Houses in Winchelsea and Caravan/Mobile Homes – Holiday Lettings - Holiday Rentals Winchelsea

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794 Holiday homes

(12) Excellent 

    15

    Winchelsea Beach holiday home rental

    Winchelsea / Winchelsea Beach

    3 6 3 nights min

    • 3 bedrooms
    • sleeps 6
    • 3 nights min
    • Beach / lakeside relaxation
    • Nearest beach 0.1 km
    • Child friendly

    from £138 / night

    £962 / week

    Book View

    Responds fast!
    avg. 3 hours 47 minutes

    from £138 / night

    (14) Very Good 

    Certificate of Excellence

      12

      Lodge rental in Winchelsea

      Rye / Winchelsea

      2 6 1 night min

      • 2 bedrooms
      • sleeps 6
      • 1 night min
      • Beach / lakeside relaxation
      • Nearest beach 1 km
      • Swimming pool

      Certificate of Excellence

      from £229 / night

      £573 / week

      Book View

      Responds fast!
      avg. 1 hour 28 minutes

      from £229 / night

      (13) Very Good 

      Certificate of Excellence

        24

        Holiday chalet in Winchelsea Beach

        Winchelsea / Winchelsea Beach

        1 3 2 nights min

        • 1 bedroom
        • sleeps 3
        • 2 nights min
        • Beach / lakeside relaxation
        • Ask owner if suitable for children
        • Private garden

        Certificate of Excellence

        from £103 / night

        £458 - £561 / week

        Book View

        from £103 / night

        (1) Excellent 

          17

          Home rental in Winchelsea

          Rye / Winchelsea

          4 6 7 nights min

          • 4 bedrooms
          • sleeps 6
          • 7 nights min
          • Beach / lakeside relaxation
          • Child friendly
          • Private garden

          from £94 / night

          £652 - £1,080 / week

          Enquire View

          from £94 / night

          (8) Excellent 

          Certificate of Excellence

            9

            Winchelsea holiday caravan/mobile home rental

            Rye / Winchelsea

            3 8 1 night min

            • 3 bedrooms
            • sleeps 8
            • 1 night min
            • Swimming pool
            • Child friendly
            • Car not necessary

            Certificate of Excellence

            from £58 / night

            £321 - £353 / week

            Book View

            Responds fast!
            avg. 1 hour 28 minutes

            from £58 / night

            (3) Excellent 

              24

              Home letting in Winchelsea

              Rye / Winchelsea

              3 8 min stay varies

              • 3 bedrooms
              • sleeps 8
              • min stay varies
              • Child friendly
              • Pet friendly
              • Private garden

              from £149 / night

              £630 - £859 / week

              Book View

              Responds fast!
              avg. 59 minutes

              from £149 / night

              (2) Average 

                31

                Winchelsea holiday home rental

                Winchelsea / Winchelsea Beach

                6 12 1 night min

                • 6 bedrooms
                • sleeps 12
                • 1 night min
                • Child friendly

                from £1,300 / night

                £1,710 / week

                Book View

                from £1,300 / night

                (5) Excellent 

                Certificate of Excellence

                  8

                  Holiday caravan/mobile home rental

                  Rye / Winchelsea

                  2 4 min stay varies

                  • 2 bedrooms
                  • sleeps 4
                  • min stay varies
                  • Swimming pool
                  • Child friendly
                  • Car not necessary

                  Certificate of Excellence

                  from £52 / night

                  £229 - £619 / week

                  Book View

                  Responds fast!
                  avg. 1 hour 28 minutes

                  from £52 / night

                  (17) Excellent 

                    27

                    Cottage rental in Winchelsea

                    Rye / Winchelsea

                    4 8 3 nights min

                    • 4 bedrooms
                    • sleeps 8
                    • 3 nights min
                    • Nearest beach 3 km
                    • Child friendly
                    • Pet friendly

                    from £287 / night

                    £1,598 / week

                    Book View

                    Responds fast!
                    avg. 2 hours 4 minutes

                    from £287 / night

                    (9) Excellent 

                    Certificate of Excellence

                      5

                      Holiday caravan/mobile home in Winchelsea

                      Rye / Winchelsea

                      2 6 min stay varies

                      • 2 bedrooms
                      • sleeps 6
                      • min stay varies
                      • Swimming pool
                      • Child friendly
                      • Car not necessary

                      Certificate of Excellence

                      from £52 / night

                      £229 - £745 / week

                      Book View

                      Responds fast!
                      avg. 1 hour 28 minutes

                      from £52 / night

                      (10) Excellent 

                      Certificate of Excellence

                        9

                        Holiday caravan/mobile home in Winchelsea

                        Rye / Winchelsea

                        2 6 min stay varies

                        • 2 bedrooms
                        • sleeps 6
                        • min stay varies
                        • Beach / lakeside relaxation
                        • Swimming pool
                        • Child friendly

                        Certificate of Excellence

                        from £63 / night

                        £298 - £476 / week

                        Book View

                        Responds fast!
                        avg. 1 hour 28 minutes

                        from £63 / night

                        (1)  

                          13

                          Holiday home in Winchelsea

                          Rye / Winchelsea

                          1 2 7 nights min

                          • 1 bedroom
                          • sleeps 2
                          • 7 nights min
                          • Beach / lakeside relaxation
                          • Child friendly
                          • Pet friendly

                          from £53 / night

                          £368 - £632 / week

                          Enquire View

                          from £53 / night

                            15

                            Holiday cottage rental

                            Rye / Winchelsea

                            2 4 7 nights min

                            • 2 bedrooms
                            • sleeps 4
                            • 7 nights min
                            • Child friendly

                            from £63 / night

                            £439 - £778 / week

                            Enquire View

                            from £63 / night

                              15

                              Home rental in Winchelsea

                              Rye / Winchelsea

                              3 5 1 night min

                              • 3 bedrooms
                              • sleeps 5
                              • 1 night min
                              • Child friendly

                              from £401 / night

                              £587 - £923 / week

                              Book View

                              from £401 / night

                                32

                                Holiday caravan/mobile home in Winchelsea

                                Rye / Winchelsea

                                2 6 min stay varies

                                • 2 bedrooms
                                • sleeps 6
                                • min stay varies
                                • Ask owner if suitable for children
                                • Ask about pets

                                from £76 / night

                                £529 / week

                                Book View

                                Responds fast!
                                avg. 51 minutes

                                from £76 / night

                                Great rentals within 20 miles that match your search

                                Distance approx 7.03 miles from Winchelsea

                                (9) Excellent 

                                  11

                                  Holiday cottage in West hill

                                  East Sussex / West hill

                                  3 7 min stay varies

                                  • 3 bedrooms
                                  • sleeps 7
                                  • min stay varies
                                  • Beach / lakeside relaxation

                                  from £86 / night

                                  £516 - £1,048 / week

                                  Book View

                                  from £86 / night

                                  Distance approx 13.16 miles from Winchelsea

                                  (42) Excellent 

                                    22

                                    Holiday barn letting

                                    Ashford / Shadoxhurst

                                    5 12 min stay varies

                                    • 5 bedrooms
                                    • sleeps 12
                                    • min stay varies
                                    • Nearest beach 15 km
                                    • Child friendly
                                    • Pet friendly

                                    from £447 / night

                                    £1,787 - £3,321 / week

                                    Book View

                                    from £447 / night

                                    Distance approx 1.97 miles from Winchelsea

                                    (29) Very Good 

                                      15

                                      Holiday apartment in Rye Centre

                                      Rye / Rye Centre

                                      2 4 min stay varies

                                      • 2 bedrooms
                                      • sleeps 4
                                      • min stay varies
                                      • Beach / lakeside relaxation
                                      • Nearest beach 4 km
                                      • Child friendly

                                      from £81 / night

                                      £324 - £718 / week

                                      Book View

                                      from £81 / night

                                      Distance approx 8.32 miles from Winchelsea

                                      (4) Excellent 

                                        54

                                        St Leonards on Sea holiday apartment rental

                                        Hastings / St Leonards on Sea

                                        3 8 5 nights min

                                        • 3 bedrooms
                                        • sleeps 8
                                        • 5 nights min
                                        • Beach / lakeside relaxation
                                        • Nearest beach 0.1 km
                                        • Child friendly

                                        from £252 / night

                                        £1,466 / week

                                        Book View

                                        from £252 / night

                                        Distance approx 13.23 miles from Winchelsea

                                          13

                                          B&b rental in Biddenden

                                          Kent / Biddenden

                                          1 2 3 nights min

                                          • 1 bedroom
                                          • sleeps 2
                                          • 3 nights min
                                          • Pet friendly
                                          • Private garden

                                          from £172 / night

                                          £1,203 / week

                                          Book View

                                          Responds fast!
                                          avg. 1 hour 20 minutes

                                          from £172 / night

                                          Distance approx 3.6 miles from Winchelsea

                                          (3) Excellent 

                                            12

                                            Holiday caravan/mobile home with shared pool, golf nearby in Camber

                                            Rye / Camber

                                            3 8 min stay varies

                                            • 3 bedrooms
                                            • sleeps 8
                                            • min stay varies
                                            • Nearest beach 1 km
                                            • Swimming pool
                                            • Child friendly

                                            from £52 / night

                                            £521 / week

                                            Book View

                                            Responds fast!
                                            avg. 3 hours 26 minutes

                                            from £52 / night

                                            Distance approx 8.25 miles from Winchelsea

                                            (44) Very Good 

                                            Certificate of Excellence

                                              18

                                              Apartment rental in St Leonards on Sea with golf nearby

                                              Hastings / St Leonards on Sea

                                              2 4 2 nights min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 2 nights min
                                              • Beach / lakeside relaxation
                                              • Child friendly
                                              • Car not necessary

                                              Certificate of Excellence

                                              from £46 / night

                                              £321 / week

                                              Book View

                                              Responds fast!
                                              avg. 40 minutes

                                              from £46 / night

                                              Distance approx 6.52 miles from Winchelsea

                                              (1) Excellent 

                                                9

                                                Holiday lodge rental

                                                Kent / New Romney

                                                1 2 7 nights min

                                                • 1 bedroom
                                                • sleeps 2
                                                • 7 nights min
                                                • Nearest beach 9 km

                                                from £74 / night

                                                £516 - £665 / week

                                                Book View

                                                Responds fast!
                                                avg. 1 hour 50 minutes

                                                from £74 / night

                                                Distance approx 5.11 miles from Winchelsea

                                                (34) Excellent 

                                                Certificate of Excellence

                                                  9

                                                  Holiday cottage rental

                                                  East Sussex / Rye

                                                  1 2 3 nights min

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • 3 nights min
                                                  • Private garden

                                                  Certificate of Excellence

                                                  from £86 / night

                                                  £561 - £619 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 2 hours 52 minutes

                                                  from £86 / night

                                                  Distance approx 12.34 miles from Winchelsea

                                                  (4) Very Good 

                                                    13

                                                    Holiday villa in Bexhill-on-Sea

                                                    East Sussex / Bexhill-on-Sea

                                                    4 9 3 nights min

                                                    • 4 bedrooms
                                                    • sleeps 9
                                                    • 3 nights min
                                                    • Child friendly
                                                    • Private garden

                                                    from £252 / night

                                                    £1,718 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 2 hours 55 minutes

                                                    from £252 / night

                                                    Distance approx 19.05 miles from Winchelsea

                                                    (13) Excellent 

                                                      25

                                                      Hythe holiday home rental

                                                      Kent / Hythe

                                                      3 6 2 nights min

                                                      • 3 bedrooms
                                                      • sleeps 6
                                                      • 2 nights min
                                                      • Child friendly
                                                      • Car not necessary
                                                      • Private garden

                                                      from £149 / night

                                                      £1,145 - £2,107 / week

                                                      Book View

                                                      from £149 / night

                                                      Distance approx 18.21 miles from Winchelsea

                                                      (43) Excellent 

                                                      Certificate of Excellence

                                                        10

                                                        Holiday barn in Heathfield

                                                        East Sussex / Heathfield

                                                        2 4 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • min stay varies
                                                        • Nearest beach 32 km
                                                        • Child friendly
                                                        • Private garden

                                                        Certificate of Excellence

                                                        from £75 / night

                                                        £447 - £865 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 58 minutes

                                                        from £75 / night

                                                        Distance approx 4.66 miles from Winchelsea

                                                        (5) Excellent 

                                                        Certificate of Excellence

                                                          23

                                                          Holiday barn in Beckley

                                                          East Sussex / Beckley

                                                          3 6 min stay varies

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Nearest beach 14 km
                                                          • Child friendly
                                                          • Pet friendly

                                                          Certificate of Excellence

                                                          from £171 / night

                                                          £716 - £1,200 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 1 hour 19 minutes

                                                          from £171 / night

                                                          Distance approx 14.35 miles from Winchelsea

                                                          (2) Excellent 

                                                            11

                                                            Dymchurch holiday apartment rental

                                                            Kent / Dymchurch

                                                            2 5 7 nights min

                                                            • 2 bedrooms
                                                            • sleeps 5
                                                            • 7 nights min
                                                            • Beach / lakeside relaxation
                                                            • Child friendly
                                                            • Car not necessary

                                                            from £57 / night

                                                            £393 - £918 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 2 hours 18 minutes

                                                            from £57 / night

                                                            Distance approx 3.38 miles from Winchelsea

                                                            (26) Excellent 

                                                              15

                                                              Holiday cottage in Camber

                                                              Rye / Camber

                                                              1 4 min stay varies

                                                              • 1 bedroom
                                                              • sleeps 4
                                                              • min stay varies
                                                              • Beach / lakeside relaxation
                                                              • Child friendly
                                                              • Pet friendly

                                                              from £92 / night

                                                              £367 - £630 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 2 hours 7 minutes

                                                              from £92 / night

                                                              Distance approx 9.93 miles from Winchelsea

                                                                16

                                                                Holiday barn in Benenden

                                                                Kent / Benenden

                                                                2 4 2 nights min

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • 2 nights min
                                                                • Nearest beach 25 km
                                                                • Pet friendly
                                                                • Private garden

                                                                from £201 / night

                                                                £911 / week

                                                                Book View

                                                                from £201 / night

                                                                Distance approx 4.65 miles from Winchelsea

                                                                (5) Excellent 

                                                                  17

                                                                  East Guldeford holiday cottage rental

                                                                  Rye / East Guldeford

                                                                  2 4 4 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 4
                                                                  • 4 nights min
                                                                  • Ask owner if suitable for children
                                                                  • Ask about pets

                                                                  from £109 / night

                                                                  £762 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 1 hour 9 minutes

                                                                  from £109 / night

                                                                  Distance approx 19.25 miles from Winchelsea

                                                                  (2) Excellent 

                                                                    18

                                                                    Holiday home rental

                                                                    East Sussex / Eastbourne

                                                                    4 6 7 nights min

                                                                    • 4 bedrooms
                                                                    • sleeps 6
                                                                    • 7 nights min
                                                                    • Nearest beach 0.1 km
                                                                    • Child friendly
                                                                    • Private garden

                                                                    from £166 / night

                                                                    £802 - £1,145 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 2 hours 51 minutes

                                                                    from £166 / night

                                                                    Distance approx 14.67 miles from Winchelsea

                                                                      24

                                                                      Etchingham holiday studio rental

                                                                      East Sussex / Etchingham

                                                                      4 10 min stay varies

                                                                      • 4 bedrooms
                                                                      • sleeps 10
                                                                      • min stay varies
                                                                      • Ask owner if suitable for children
                                                                      • Ask about pets

                                                                      from £220 / night

                                                                      £1,539 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 51 minutes

                                                                      from £220 / night

                                                                      Distance approx 3.42 miles from Winchelsea

                                                                      (13) Very Good 

                                                                        17

                                                                        Camber holiday chalet rental

                                                                        Rye / Camber

                                                                        3 8 2 nights min

                                                                        • 3 bedrooms
                                                                        • sleeps 8
                                                                        • 2 nights min
                                                                        • Beach / lakeside relaxation
                                                                        • Swimming pool
                                                                        • Child friendly

                                                                        from £92 / night

                                                                        £481 - £785 / week

                                                                        Book View

                                                                        from £92 / night

                                                                        Distance approx 3.4 miles from Winchelsea

                                                                          8

                                                                          Camber holiday caravan/mobile home rental

                                                                          Rye / Camber

                                                                          3 6 1 night min

                                                                          • 3 bedrooms
                                                                          • sleeps 6
                                                                          • 1 night min
                                                                          • Nearest beach 0.5 km
                                                                          • Swimming pool
                                                                          • Child friendly

                                                                          from £63 / night

                                                                          £453 - £2,290 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 11 minutes

                                                                          from £63 / night

                                                                          Distance approx 6.78 miles from Winchelsea

                                                                          (28) Excellent 

                                                                            21

                                                                            Holiday townhouse in Central Hastings

                                                                            Hastings / Central Hastings

                                                                            4 8 7 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 8
                                                                            • 7 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Nearest beach 2 km
                                                                            • Child friendly

                                                                            from £123 / night

                                                                            £859 - £1,260 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 1 hour 54 minutes

                                                                            from £123 / night

                                                                            Distance approx 3.6 miles from Winchelsea

                                                                              6

                                                                              Camber holiday caravan/mobile home rental

                                                                              Rye / Camber

                                                                              3 8 min stay varies

                                                                              • 3 bedrooms
                                                                              • sleeps 8
                                                                              • min stay varies
                                                                              • Child friendly
                                                                              • Pet friendly

                                                                              from £229 / night

                                                                              £413 - £859 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 3 hours 12 minutes

                                                                              from £229 / night

                                                                              Distance approx 5.24 miles from Winchelsea

                                                                                7

                                                                                Holiday caravan/mobile home with shared pool in Hastings

                                                                                East Sussex / Hastings

                                                                                3 6 2 nights min

                                                                                • 3 bedrooms
                                                                                • sleeps 6
                                                                                • 2 nights min
                                                                                • Nearest beach 7 km
                                                                                • Swimming pool
                                                                                • Child friendly

                                                                                from £98 / night

                                                                                £682 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 3 hours 10 minutes

                                                                                from £98 / night

                                                                                Distance approx 2.77 miles from Winchelsea

                                                                                  26

                                                                                  Hastings holiday caravan/mobile home rental

                                                                                  East Sussex / Hastings

                                                                                  2 6 7 nights min

                                                                                  • 2 bedrooms
                                                                                  • sleeps 6
                                                                                  • 7 nights min
                                                                                  • Child friendly

                                                                                  from £90 / night

                                                                                  £630 / week

                                                                                  Book View

                                                                                  from £90 / night

                                                                                  Top Destination reviews

                                                                                  Winchelsea Beach - Beautiful Beach House
                                                                                  Amazing beach house!

                                                                                  We have just arrived home from the most fantastic short break in this magical beach house! I honestly fell in love with this beautiful property. It was such a delight to stay in a rental that you could tell was so very loved and well looked after by its owners. The interior was immaculate, and the owners were so helpful, answering any questions/queries straight away. We miss it already and will definitely be back! see more
                                                                                  The Post Office - Winchelsea (near Rye)
                                                                                  Excellent value - but do take a car!

                                                                                  7 of us enjoyed a long weekend at the Old Post Office and had a great time during our stay. The house is tucked away in picturesque Winchelsea and is great for short walks and a little exploring as there is lots of rich history here. The rooms were all beautiful and clean - beds were very comfy! The house had everything we needed, and the outdoor patio area was a lovely addition. The owners are extremely helpful and responsive and sent us a welcome pack 2 weeks before our arrival. Only one of us was able to drive so this did make popping to the shops a little difficult as the nearest Co-op is a 30 minute walk away, and getting to the beach takes even longer, so I would recommend you take a car and don't rely too much on public transport when coming here. The Post Office is excellent value and I would happily recommend it to others. I only wish we could have stayed longer.see more
                                                                                  Cordwainers - sleeps 8 in 4 bedrooms
                                                                                  stunning views ,great location ,lovely house

                                                                                  this is now our second stay at Cordwainers , we were impressed as the first time we came in Jan 2016 , stunning views towards Rye from the garden , the house itself is extremely well maintained by the owner , the rooms very comfy as well as the beds , a view even from both shower rooms is even better in the morning , everything about this home is family friendly a perfect holiday let in a great location , great local shop providing local cheese meats fruit & veg , terrific local pub New Inn does cracking food great choice of beers ,and a stunning beer garden , the church of St Thomas has a unique history as does Winchelsea itself ,the Museum is also well worth a visit too with some great books by local historian Malcolm Pratt that are a must read " Winchelsea : the tale of a medieval town" is his first covering up to the 18th century the second is "Winchelsea : a port of stranded pride! also being close to Rye and Hastings makes Winchelsea an ideal holiday base for many local attractions , the views from all four points of the compass in Winchelsea are pretty amazing , will certainly be returning to Cordwainers next year and must thank Helen for the bubbly and lovely chocolates you could not wish for a more helpful or genuine host many thanks Helensee more
                                                                                  Jasmine Caravan
                                                                                  brilliant caravan

                                                                                  everything you need is on park coop just outside gates another pub but club on site very good had no need to go to other pub club food good and good prices.caravan exceptional clean tidy and very well equiped even down to dog treats for our two dogs left in caravan aswell as milk/tea/coffee/buscuits ten out of tensee more
                                                                                  Sandy Shores - 6 Berth with Deck frontage
                                                                                  Thoroughly well Provided for Guests

                                                                                  Very impressed with Owners Caravan and Manager. Could not find any negative comment as everything had been well planned to make this an enjoyable stay. We found the location excellent and so near the beach … see more
                                                                                  'Beach Belle' - Gold Standard Caravan.
                                                                                  Very Nice

                                                                                  Very nice caravan, clean and welcome. Happy to come back soon. Had sone nice days at Winchelsea and Rye. … see more
                                                                                  Seascape - 6 berth home from home
                                                                                  Excellent, clean accommodation

                                                                                  Good site, near a well stocked shop. Good facilities everywhere. Near recreation ground for dog walking. Very comfortable accommodation with everything needed within. Site owners need to tarmac road where we stayed. Very deep puddles and impossible to get to waste bins when we left. Had to take rubbish home.see more
                                                                                  Winchelsea Beach Holiday Annex with river frontage
                                                                                  fantastic place

                                                                                  lovely place very pretty garden great views and great fishing lovely touch the wine and chocs would love to go again in fact we want to move in … see more

                                                                                  Also consider