Cottages in Winster and Holiday rentals - Holiday Lettings - Holiday Rentals Winster

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1,392 Holiday homes

(159) Excellent 

    22

    Cottage rental in Winster

    Peak District National Park / Winster

    3 7 min stay varies

    • 3 bedrooms
    • sleeps 7
    • min stay varies
    • Child friendly
    • Private garden
    “The cottage is very well equipped and comfortable” First impressions were how clean it was. We were here for a weekend and the only disappointment was that we didn't have enough time to use all of the equipment! We tried very hard to use all of the sitting areas. The cosy lounge was first while watching the TV (no time for a film). In the morning it was reading the papers in the games room and finally the garden room Sunday afternoon. I would recommend for larger groups as plenty of room to spread out while also enough space to be together. The location was ideal for walking cycling and the shops in Matlock are nearby if needed. We only saw our hosts briefly (which suited us) but were encouraged and able to contact them easily if we required anything.

    from £49 / night

    £345 - £1,195 / week

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    from £49 / night

    (53) Excellent 

      16

      Barn rental in Winster

      Peak District National Park / Winster

      3 5 2 nights min

      • 3 bedrooms
      • sleeps 5
      • 2 nights min
      • Child friendly
      “A really comfortable stay with village and countryside on the doorstep” This tastefully furnished and very well eqiupped cottage had everything we needed for a great stay. The living/dining room is larger and more comfortable than the photos convey. There are plenty of walks on the doorstep or a short drive away, and the village is adequately equipped for groceries and a choice of two pubs. The visitor information was valuable, particularly the ordnance survey. We couldn't have wanted for more.

      from £92 / night

      £630 - £745 / week

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      Responds fast!
      avg. 1 hour 56 minutes

      from £92 / night

      (32) Excellent 

        17

        Winster holiday cottage rental

        Peak District National Park / Winster

        1 2 2 nights min

        • 1 bedroom
        • sleeps 2
        • 2 nights min
        • Nearest beach 165 km
        • Child friendly

        from £80 / night

        £350 - £360 / week

        Enquire View

        from £80 / night

          24

          Holiday home rental

          Peak District National Park / Winster

          3 6 7 nights min

          • 3 bedrooms
          • sleeps 6
          • 7 nights min
          • Child friendly
          • Private garden

          from £72 / night

          £504 - £913 / week

          Enquire View

          from £72 / night

          (5) Very Good 

            19

            Home rental in Winster

            Peak District National Park / Winster

            6 18 min stay varies

            • 6 bedrooms
            • sleeps 18
            • min stay varies
            • Child friendly
            • Pet friendly

            from £686 / night

            £4,801 / week

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            from £686 / night

            (75) Very Good 

            Certificate of Excellence

              25

              Holiday cottage in Winster

              Peak District National Park / Winster

              2 5 3 nights min

              • 2 bedrooms
              • sleeps 5
              • 3 nights min
              • Child friendly
              • Pet friendly
              • Private garden
              “Exellent holiday cottage” We spent a wonderful 4 days here in the Peak District. The cottage is absolutely perfect and very well located in a super village with 2 pubs and a small shop. The owner was incredibly helpful - we would definitely stay here again.

              Certificate of Excellence

              from £98 / night

              £579 - £766 / week

              Book View

              Responds fast!
              avg. 3 hours 33 minutes

              from £98 / night

              (5) Excellent 

                17

                Winster holiday cottage accommodation

                Peak District National Park / Winster

                1 2 2 nights min

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

                from £75 / night

                £430 / week

                Book View

                from £75 / night

                (8) Excellent 

                  19

                  Holiday cottage rental

                  Peak District National Park / Winster

                  2 4 min stay varies

                  • 2 bedrooms
                  • sleeps 4
                  • min stay varies
                  • Ask owner if suitable for children
                  • Private garden

                  from £92 / night

                  £550 - £669 / week

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                  from £92 / night

                    19

                    Holiday home in Winster

                    Peak District National Park / Winster

                    2 4 7 nights min

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

                    from £61 / night

                    £425 - £727 / week

                    Enquire View

                    from £61 / night

                    (13) Very Good 

                      14

                      Holiday cottage in Winster

                      Peak District National Park / Winster

                      1 2 3 nights min

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

                      from £86 / night

                      £602 / week

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                      Responds fast!
                      avg. 1 hour 59 minutes

                      from £86 / night

                        16

                        Winster holiday cottage let

                        Peak District National Park / Winster

                        2 3 7 nights min

                        • 2 bedrooms
                        • sleeps 3
                        • 7 nights min
                        • Child friendly
                        • Pet friendly
                        • Private garden

                        from £53 / night

                        £368 - £642 / week

                        Enquire View

                        from £53 / night

                        (7) Excellent 

                          9

                          Holiday home in Winster

                          Peak District National Park / Winster

                          3 7 3 nights min

                          • 3 bedrooms
                          • sleeps 7
                          • 3 nights min
                          • Child friendly
                          • Private garden

                          from £108 / night

                          £406 - £1,149 / week

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                          from £108 / night

                          (5) Excellent 

                            15

                            Holiday home in Winster

                            Peak District National Park / Winster

                            2 4 3 nights min

                            • 2 bedrooms
                            • sleeps 4
                            • 3 nights min
                            • Child friendly
                            • Pet friendly

                            from £85 / night

                            £357 - £850 / week

                            Enquire View

                            from £85 / night

                            (17) Excellent 

                              18

                              Home letting in Winster

                              Peak District National Park / Winster

                              1 2 3 nights min

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

                              from £64 / night

                              £298 - £679 / week

                              Enquire View

                              from £64 / night

                              (5) Excellent 

                                19

                                Winster holiday home rental

                                Peak District National Park / Winster

                                2 2 3 nights min

                                • 2 bedrooms
                                • sleeps 2
                                • 3 nights min
                                • Child friendly

                                from £85 / night

                                £269 - £714 / week

                                Enquire View

                                from £85 / night

                                (11) Very Good 

                                  6

                                  Holiday home in Winster

                                  Peak District National Park / Winster

                                  2 3 3 nights min

                                  • 2 bedrooms
                                  • sleeps 3
                                  • 3 nights min
                                  • Child friendly

                                  from £73 / night

                                  £290 - £709 / week

                                  Enquire View

                                  from £73 / night

                                  (1) Excellent 

                                    10

                                    Home letting in Winster

                                    Peak District National Park / Winster

                                    1 2 3 nights min

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

                                    from £110 / night

                                    £349 - £890 / week

                                    Enquire View

                                    from £110 / night

                                      15

                                      Holiday home in Winster

                                      Peak District National Park / Winster

                                      2 4 3 nights min

                                      • 2 bedrooms
                                      • sleeps 4
                                      • 3 nights min
                                      • Child friendly
                                      • Pet friendly
                                      • Private garden

                                      from £88 / night

                                      £305 - £889 / week

                                      Enquire View

                                      from £88 / night

                                      (13) Very Good 

                                        10

                                        Holiday home accommodation

                                        Peak District National Park / Winster

                                        1 2 3 nights min

                                        • 1 bedroom
                                        • sleeps 2
                                        • 3 nights min
                                        • Child friendly

                                        from £77 / night

                                        £231 - £554 / week

                                        Enquire View

                                        from £77 / night

                                          17

                                          Holiday home with golf nearby in Winster

                                          Peak District National Park / Winster

                                          3 6 3 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 3 nights min
                                          • Pet friendly
                                          • Private garden

                                          from £121 / night

                                          £457 - £1,253 / week

                                          Enquire View

                                          from £121 / night

                                          (3) Excellent 

                                            30

                                            Winster holiday home rental

                                            Peak District National Park / Winster

                                            6 14 3 nights min

                                            • 6 bedrooms
                                            • sleeps 14
                                            • 3 nights min
                                            • Child friendly
                                            • Private garden

                                            from £444 / night

                                            £1,557 - £5,751 / week

                                            Enquire View

                                            from £444 / night

                                            (16) Very Good 

                                              17

                                              Winster holiday home rental

                                              Peak District National Park / Winster

                                              3 7 3 nights min

                                              • 3 bedrooms
                                              • sleeps 7
                                              • 3 nights min
                                              • Child friendly
                                              • Private garden

                                              from £89 / night

                                              £372 - £1,058 / week

                                              Enquire View

                                              from £89 / night

                                              (3) Very Good 

                                                12

                                                Home rental in Winster

                                                Peak District National Park / Winster

                                                4 8 3 nights min

                                                • 4 bedrooms
                                                • sleeps 8
                                                • 3 nights min
                                                • Child friendly

                                                from £179 / night

                                                £669 - £2,093 / week

                                                Enquire View

                                                from £179 / night

                                                (3) Average 

                                                  13

                                                  Holiday home with golf nearby in Winster

                                                  Peak District National Park / Winster

                                                  2 3 3 nights min

                                                  • 2 bedrooms
                                                  • sleeps 3
                                                  • 3 nights min
                                                  • Child friendly
                                                  • Pet friendly

                                                  from £97 / night

                                                  £335 - £954 / week

                                                  Enquire View

                                                  from £97 / night

                                                    15

                                                    Holiday home rental

                                                    Peak District National Park / Winster

                                                    2 4 3 nights min

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

                                                    from £94 / night

                                                    £323 - £839 / week

                                                    Enquire View

                                                    from £94 / night

                                                    (3) Excellent 

                                                      10

                                                      Holiday home in Winster

                                                      Peak District National Park / Winster

                                                      2 4 3 nights min

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • 3 nights min
                                                      • Private garden

                                                      from £87 / night

                                                      £335 - £828 / week

                                                      Enquire View

                                                      from £87 / night

                                                      (7) Very Good 

                                                        8

                                                        Holiday home in Winster

                                                        Peak District National Park / Winster

                                                        3 6 3 nights min

                                                        • 3 bedrooms
                                                        • sleeps 6
                                                        • 3 nights min
                                                        • Child friendly
                                                        • Private garden

                                                        from £95 / night

                                                        £339 - £1,112 / week

                                                        Enquire View

                                                        from £95 / night

                                                        (8) Excellent 

                                                          17

                                                          Home letting in Winster

                                                          Peak District National Park / Winster

                                                          7 16 3 nights min

                                                          • 7 bedrooms
                                                          • sleeps 16
                                                          • 3 nights min
                                                          • Child friendly
                                                          • Pet friendly
                                                          • Private garden

                                                          from £552 / night

                                                          £1,946 - £7,091 / week

                                                          Enquire View

                                                          from £552 / night

                                                            16

                                                            Holiday cottage in Winster

                                                            Peak District National Park / Winster

                                                            2 3 3 nights min

                                                            • 2 bedrooms
                                                            • sleeps 3
                                                            • 3 nights min
                                                            • Child friendly

                                                            from £95 / night

                                                            £335 - £901 / week

                                                            Enquire View

                                                            from £95 / night

                                                            Great rentals within 20 miles that match your search

                                                            Distance approx 6.76 miles from Winster

                                                            (5) Very Good 

                                                            Certificate of Excellence

                                                              20

                                                              Monyash holiday barn rental

                                                              Derbyshire / Monyash

                                                              3 6 min stay varies

                                                              • 3 bedrooms
                                                              • sleeps 6
                                                              • min stay varies
                                                              • Child friendly
                                                              • Private garden

                                                              Certificate of Excellence

                                                              from £126 / night

                                                              £642 - £1,082 / week

                                                              Book View

                                                              from £126 / night

                                                              Distance approx 19.61 miles from Winster

                                                              (34) Excellent 

                                                              Certificate of Excellence

                                                                8

                                                                Holiday shepherds hut in Buxton

                                                                Derbyshire / Buxton

                                                                1 2 1 night min

                                                                • 1 bedroom
                                                                • sleeps 2
                                                                • 1 night min
                                                                • Suitable for children age 5+
                                                                • Pet friendly
                                                                • Private garden

                                                                Certificate of Excellence

                                                                from £81 / night

                                                                £401 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 2 hours 18 minutes

                                                                from £81 / night

                                                                Distance approx 9.89 miles from Winster

                                                                  4

                                                                  Holiday home in Clay Cross

                                                                  Chesterfield / Clay Cross

                                                                  4 8 3 nights min

                                                                  • 4 bedrooms
                                                                  • sleeps 8
                                                                  • 3 nights min
                                                                  • Child friendly

                                                                  from £98 / night

                                                                  £682 / week

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                                                                  Responds fast!
                                                                  avg. 2 hours 50 minutes

                                                                  from £98 / night

                                                                  Distance approx 3.41 miles from Winster Show on Map

                                                                  (32) Very Good 

                                                                  Certificate of Excellence

                                                                    24

                                                                    Holiday cottage in Matlock

                                                                    Derbyshire / Matlock

                                                                    2 4 2 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • 2 nights min
                                                                    • Suitable for children age 5+

                                                                    Certificate of Excellence

                                                                    from £115 / night

                                                                    £573 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 9 minutes

                                                                    from £115 / night

                                                                    Distance approx 12.77 miles from Winster

                                                                    (1) Excellent 

                                                                      15

                                                                      Ellastone holiday cottage accommodation

                                                                      Staffordshire / Ellastone

                                                                      3 6 min stay varies

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • min stay varies
                                                                      • Child friendly
                                                                      • Private garden

                                                                      from £229 / night

                                                                      £1,546 - £2,348 / week

                                                                      Book View

                                                                      from £229 / night

                                                                      Distance approx 12.57 miles from Winster

                                                                        12

                                                                        Holiday camper van in Belper

                                                                        Derbyshire / Belper

                                                                        2 4 2 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 4
                                                                        • 2 nights min
                                                                        • Child friendly
                                                                        • Air conditioning

                                                                        from £58 / night

                                                                        £401 / week

                                                                        Book View

                                                                        from £58 / night

                                                                        Distance approx 12.57 miles from Winster

                                                                        (28) Very Good 

                                                                          24

                                                                          Holiday barn in Winkhill

                                                                          Leek / Winkhill

                                                                          3 8 min stay varies

                                                                          • 3 bedrooms
                                                                          • sleeps 8
                                                                          • min stay varies
                                                                          • Child friendly
                                                                          • Ask about pets

                                                                          from £126 / night

                                                                          £796 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 2 hours 56 minutes

                                                                          from £126 / night

                                                                          Distance approx 6.73 miles from Winster

                                                                          (21) Very Good 

                                                                            18

                                                                            Holiday cottage in Monyash

                                                                            Derbyshire / Monyash

                                                                            2 4 3 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 4
                                                                            • 3 nights min
                                                                            • Suitable for children age 5+

                                                                            from £81 / night

                                                                            £401 - £607 / week

                                                                            Book View

                                                                            from £81 / night

                                                                            Distance approx 13.33 miles from Winster

                                                                            (2) Excellent 

                                                                              13

                                                                              Holiday home in Buxton

                                                                              Derbyshire / Buxton

                                                                              2 4 2 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • 2 nights min
                                                                              • Child friendly
                                                                              • Pet friendly
                                                                              • Private garden

                                                                              from £75 / night

                                                                              £521 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 3 hours 56 minutes

                                                                              from £75 / night

                                                                              Distance approx 14.75 miles from Winster

                                                                                12

                                                                                Holiday chalet in Uttoxeter

                                                                                Staffordshire / Uttoxeter

                                                                                1 4 1 night min

                                                                                • 1 bedroom
                                                                                • sleeps 4
                                                                                • 1 night min
                                                                                • Child friendly
                                                                                • Ask about pets

                                                                                from £155 / night

                                                                                £928 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 1 hour 59 minutes

                                                                                from £155 / night

                                                                                Distance approx 16.69 miles from Winster

                                                                                  6

                                                                                  Holiday apartment in Sheffield

                                                                                  South Yorkshire / Sheffield

                                                                                  3 10 4 nights min

                                                                                  • 3 bedrooms
                                                                                  • sleeps 10
                                                                                  • 4 nights min
                                                                                  • Child friendly
                                                                                  • Air conditioning
                                                                                  • Pet friendly

                                                                                  from £252 / night

                                                                                  £1,764 / week

                                                                                  Book View

                                                                                  from £252 / night

                                                                                  Top Destination reviews

                                                                                  Derbyshire Village House sleeping up to 18 adults, pub, shop in walking distance
                                                                                  Great House

                                                                                  My aunty booked this for our family for a long weekend - what I found out when I got there is that my ancestors used to actually own the house and my Granddad who was with us had grew up there. Fantastic and beautiful old house located in a quaint little village with plenty of family history. Even without the family history - I would recommend staying here to anyone.see more
                                                                                  Ivy Cottage, Peak District Luxury Accomodation
                                                                                  Beautiful cottage in a lovely quaint village.

                                                                                  Spent 4 nights in this beautiful cottage. Matt and Becky made a wonderful job of ensuring everything was available for us. Everything we needed was in the cottage. They had even put a welcome basket out for us. We enjoyed it so much we have already booked to go again next month. … see more
                                                                                  The Old Barn
                                                                                  Ex uni get together

                                                                                  Very comfortable and clean cottage. Poor phone recep but wifi good. SharonT is very friendly. She let us stay on till after lunch as she had a day gap before the next guests. Thank you Sharon! … see more
                                                                                  Briar Cottage,Peak District National Park, Winster
                                                                                  Beautiful period cottage. Cosy

                                                                                  Super little cottage nestled in the heart of Winster. Every comfort catered for. A lovely period cottage with stylish, contemporary kitchen and bathroom. Thoroughly enjoyed our stay. Great little pubs nearby with plenty of character, nice food and drink, and very pleasant staff. Great walk over to Stanton Moor. Fabulous all round. Many thanks!see more
                                                                                  The Croft Winster
                                                                                  Best Christmas

                                                                                  What a fantastic cottage in the most picturesque village served by a great little friendly shop and 2 welcoming pubs. The cottage had lots of character and charm was also well appointed warm and clean. Highly recommend as this all helped us have a fantastic Christmas … see more
                                                                                  The Spook cosy detached cottage with garden and off road parking
                                                                                  Lovely

                                                                                  The cutest house in a perfect little village. Hiking trails just around the corner and close to Matlock Bath, Haddon Hall and Chatsworth. I explored the area by myself and couldn't be more pleased. The owner was very nice and helpful. She stood outside waiting for me when I arrived after midnight! The house is quite simply decorated and had everything I needed. I loved the view from the windows and the cute little garden. The wi-fi was great in every part of the house. I highly recommend staying at the Spook!see more

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