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704 Holiday homes

(61) Excellent 

    11

    Itton holiday cottage rental

    Chepstow / Itton

    2 4 min stay varies

    • 2 bedrooms
    • sleeps 4
    • min stay varies
    • Child friendly
    • Pet friendly
    “Amazing cottage with stunning garden and views to die for” Helen was the perfect 'host' she was there when we needed any information and was discreet when we were happy to stay 'at home'. The cottage was incredibly well equipped and cosy. The furnishings were wonderful and reminded us of family homes, a mixture of interesting and well loved pieces. A car would be required to stay at the cottage as it is set in countryside but parking is off road. Our two dogs, Ellie and Barney were made especially welcome which made the whole experience enjoyable without being anxious about them. The location of the property is close to some fantastic walks and Helen gave us easy directions to them. We couldn't fault the whole experience (apart from we could have had better weather) and look forward to booking again for next year.

    from £103 / night

    £481 - £613 / week

    Book View

    from £103 / night

    (30) Excellent 

      10

      Itton holiday barn let

      Chepstow / Itton

      1 2 min stay varies

      • 1 bedroom
      • sleeps 2
      • min stay varies
      • Child friendly
      • Pet friendly
      “Felt like home” If you are looking for a retreat from the hussle and bussle of every day life then Dolly's Barn is the place to stay. Warm, cosy and full of character. Stunning views and beautiful scenery. The owner Helen was very welcoming and made me feel at home. There were so many great walks nearby for me and my dogs. After being out and about during the day, curling up in front of the wood burning stove of an evening was such a treat. I had such an amazing week that I have already booked again for next year!!! I would highly recommend Dolly's Barn to other people.

      from £98 / night

      £453 - £498 / week

      Book View

      from £98 / night

      (20) Excellent 

        24

        Holiday cottage in Brockweir

        Chepstow / Brockweir

        1 2 min stay varies

        • 1 bedroom
        • sleeps 2
        • min stay varies
        • Nearest beach 90 km
        • Private garden

        from £81 / night

        £470 - £510 / week

        Book View

        Responds fast!
        avg. 1 hour 50 minutes

        from £81 / night

          35

          Holiday home in Chepstow

          Monmouthshire / Chepstow

          3 9 2 nights min

          • 3 bedrooms
          • sleeps 9
          • 2 nights min
          • Child friendly
          • Pet friendly
          • Private garden

          from £401 / night

          £2,806 / week

          Book View

          Responds fast!
          avg. 44 minutes

          from £401 / night

          (16) Very Good 

            19

            Holiday cottage in Brockweir

            Chepstow / Brockweir

            2 4 min stay varies

            • 2 bedrooms
            • sleeps 4
            • min stay varies
            • Nearest beach 100 km
            • Child friendly
            • Pet friendly

            from £84 / night

            £556 - £829 / week

            Book View

            from £84 / night

            (70) Excellent 

              17

              Holiday tower with golf nearby in Mathern

              Chepstow / Mathern

              1 2 min stay varies

              • 1 bedroom
              • sleeps 2
              • min stay varies

              from £115 / night

              £561 / week

              Book View

              Responds fast!
              avg. 17 minutes

              from £115 / night

              (2) Very Good 

                19

                Chepstow holiday home rental

                Monmouthshire / Chepstow

                3 6 3 nights min

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

                from £287 / night

                £1,718 - £2,519 / week

                Book View

                from £287 / night

                  5

                  Chepstow holiday log cabin rental

                  Monmouthshire / Chepstow

                  1 3 1 night min

                  • 1 bedroom
                  • sleeps 3
                  • 1 night min
                  • Nearest beach 50 km
                  • Car not necessary
                  • Air conditioning

                  from £103 / night

                  £722 / week

                  Book View

                  from £103 / night

                  (58) Excellent 

                    17

                    Chepstow holiday cottage rental

                    Monmouthshire / Chepstow

                    2 4 min stay varies

                    • 2 bedrooms
                    • sleeps 4
                    • min stay varies
                    • Ask owner if suitable for children
                    • Pet friendly
                    “Amazing cottage with stunning garden and views to die for” Helen was the perfect 'host' she was there when we needed any information and was discreet when we were happy to stay 'at home'. The cottage was incredibly well equipped and cosy. The furnishings were wonderful and reminded us of family homes, a mixture of interesting and well loved pieces. A car would be required to stay at the cottage as it is set in countryside but parking is off road. Our two dogs, Ellie and Barney were made especially welcome which made the whole experience enjoyable without being anxious about them. The location of the property is close to some fantastic walks and Helen gave us easy directions to them. We couldn't fault the whole experience (apart from we could have had better weather) and look forward to booking again for next year.

                    from £109 / night

                    £458 - £613 / week

                    Book View

                    from £109 / night

                      26

                      Chepstow holiday b&b rental

                      Monmouthshire / Chepstow

                      2 4 1 night min

                      • 2 bedrooms
                      • sleeps 4
                      • 1 night min
                      • Child friendly
                      • Ask about pets
                      • Private garden

                      from £172 / night

                      £1,145 / week

                      Book View

                      from £172 / night

                      (23) Excellent 

                        8

                        Home rental in Chepstow

                        Monmouthshire / Chepstow

                        1 2 6 nights min

                        • 1 bedroom
                        • sleeps 2
                        • 6 nights min
                        • Child friendly
                        • Pet friendly
                        “Felt like home” If you are looking for a retreat from the hussle and bussle of every day life then Dolly's Barn is the place to stay. Warm, cosy and full of character. Stunning views and beautiful scenery. The owner Helen was very welcoming and made me feel at home. There were so many great walks nearby for me and my dogs. After being out and about during the day, curling up in front of the wood burning stove of an evening was such a treat. I had such an amazing week that I have already booked again for next year!!! I would highly recommend Dolly's Barn to other people.

                        from £103 / night

                        £447 / week

                        Book View

                        from £103 / night

                        Great rentals within 20 miles that match your search

                        Distance approx 14.85 miles from Chepstow

                        (5) Excellent 

                          4

                          Holiday caravan/mobile home in Pucklechurch

                          Gloucestershire / Pucklechurch

                          1 5 3 nights min

                          • 1 bedroom
                          • sleeps 5
                          • 3 nights min
                          • Child friendly
                          • Pet friendly

                          from £103 / night

                          £722 / week

                          Book View

                          from £103 / night

                          Distance approx 15.76 miles from Chepstow

                          (2) Excellent 

                            24

                            Home rental in Rogerstone

                            Newport / Rogerstone

                            6 8 min stay varies

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

                            from £161 / night

                            £779 - £1,374 / week

                            Book View

                            from £161 / night

                            Distance approx 13.51 miles from Chepstow

                              4

                              Bristol holiday camper van rental

                              England / Bristol

                              1 4 3 nights min

                              • 1 bedroom
                              • sleeps 4
                              • 3 nights min
                              • Child friendly

                              from £103 / night

                              £722 / week

                              Book View

                              from £103 / night

                              Distance approx 15.19 miles from Chepstow

                              (7) Very Good 

                                33

                                Abergavenny holiday cottage rental

                                Monmouthshire / Abergavenny

                                2 4 2 nights min

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

                                from £166 / night

                                £567 / week

                                Book View

                                from £166 / night

                                Distance approx 11.96 miles from Chepstow

                                  18

                                  Cottage letting in Blakeney

                                  Forest of Dean / Blakeney

                                  2 4 min stay varies

                                  • 2 bedrooms
                                  • sleeps 4
                                  • min stay varies
                                  • Child friendly
                                  • Pet friendly
                                  • Private garden

                                  from £163 / night

                                  £1,134 - £1,369 / week

                                  Book View

                                  from £163 / night

                                  Distance approx 12.72 miles from Chepstow

                                    12

                                    Bristol holiday apartment rental

                                    England / Bristol

                                    1 3 2 nights min

                                    • 1 bedroom
                                    • sleeps 3
                                    • 2 nights min
                                    • Ask owner if suitable for children

                                    from £81 / night

                                    £561 / week

                                    Book View

                                    Responds fast!
                                    avg. 2 hours 14 minutes

                                    from £81 / night

                                    Distance approx 13.51 miles from Chepstow

                                      4

                                      Bristol holiday camper van rental

                                      England / Bristol

                                      1 5 3 nights min

                                      • 1 bedroom
                                      • sleeps 5
                                      • 3 nights min
                                      • Child friendly
                                      • Pet friendly

                                      from £103 / night

                                      £722 / week

                                      Book View

                                      from £103 / night

                                      Distance approx 11.99 miles from Chepstow

                                      (22) Excellent 

                                        25

                                        Holiday cottage in Blakeney

                                        Forest of Dean / Blakeney

                                        2 4 3 nights min

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

                                        from £92 / night

                                        £687 / week

                                        Book View

                                        Responds fast!
                                        avg. 1 hour 49 minutes

                                        from £92 / night

                                        Distance approx 17.35 miles from Chepstow

                                        (12) Excellent 

                                          18

                                          Holiday barn with golf nearby in Nympsfield

                                          Gloucestershire / Nympsfield

                                          2 4 min stay varies

                                          • 2 bedrooms
                                          • sleeps 4
                                          • min stay varies
                                          • Child friendly
                                          • Pet friendly

                                          from £81 / night

                                          £498 - £756 / week

                                          Book View

                                          from £81 / night

                                          Distance approx 19.46 miles from Chepstow

                                            29

                                            Holiday b&b in Abergavenny

                                            Monmouthshire / Abergavenny

                                            1 2 1 night min

                                            • 1 bedroom
                                            • sleeps 2
                                            • 1 night min
                                            • Private garden

                                            from £89 / night

                                            £618 / week

                                            Book View

                                            from £89 / night

                                            Distance approx 15.06 miles from Chepstow

                                              29

                                              Holiday home in Lydbrook

                                              Forest of Dean / Lydbrook

                                              8 16 3 nights min

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

                                              from £630 / night

                                              £1,947 - £5,004 / week

                                              Book View

                                              from £630 / night

                                              Distance approx 13.56 miles from Chepstow

                                              (66) Excellent 

                                                30

                                                Holiday cottage letting

                                                Monmouthshire / Usk

                                                2 3 min stay varies

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

                                                from £114 / night

                                                £469 - £1,224 / week

                                                Book View

                                                Responds fast!
                                                avg. 1 hour 58 minutes

                                                from £114 / night

                                                Distance approx 13.03 miles from Chepstow

                                                (12) Very Good 

                                                  20

                                                  Holiday studio in Bristol

                                                  Bristol / Central Bristol

                                                  Studio 2 2 nights min

                                                  • Studio
                                                  • sleeps 2
                                                  • 2 nights min
                                                  • Nearest beach 30 km
                                                  • Child friendly
                                                  • Car not necessary

                                                  from £92 / night

                                                  £642 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 3 hours 42 minutes

                                                  from £92 / night

                                                  Distance approx 13 miles from Chepstow

                                                  (42) Excellent 

                                                  Certificate of Excellence

                                                    66

                                                    Holiday cottage in Bristol

                                                    Bristol / Clifton, Bristol

                                                    2 4 2 nights min

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • 2 nights min
                                                    • Nearest beach 21 km
                                                    • Child friendly
                                                    • Car not necessary

                                                    Certificate of Excellence

                                                    from £126 / night

                                                    £974 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 50 minutes

                                                    from £126 / night

                                                    Distance approx 14.11 miles from Chepstow

                                                    (23) Excellent 

                                                      11

                                                      Holiday cottage in Whitchurch, Herefordshire

                                                      Ross-on-Wye / Whitchurch, Herefordshire

                                                      4 8 min stay varies

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

                                                      from £172 / night

                                                      £585 - £1,810 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 3 hours 16 minutes

                                                      from £172 / night

                                                      Distance approx 18.91 miles from Chepstow

                                                      (5) Average 

                                                        28

                                                        Abergavenny holiday cottage rental

                                                        Monmouthshire / Abergavenny

                                                        1 6 2 nights min

                                                        • 1 bedroom
                                                        • sleeps 6
                                                        • 2 nights min
                                                        • Nearest beach 0 km
                                                        • Child friendly
                                                        • Ask about pets

                                                        from £69 / night

                                                        £413 / week

                                                        Book View

                                                        from £69 / night

                                                        Distance approx 16.16 miles from Chepstow

                                                        (5) Excellent 

                                                          19

                                                          Holiday barn in Whitchurch

                                                          Ross-on-Wye / Whitchurch

                                                          2 4 2 nights min

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

                                                          from £166 / night

                                                          £1,163 / week

                                                          Book View

                                                          from £166 / night

                                                          Distance approx 14.81 miles from Chepstow

                                                          (3) Very Good 

                                                            7

                                                            Symonds Yat holiday cottage rental

                                                            Ross-on-Wye / Symonds Yat

                                                            2 2 2 nights min

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

                                                            from £86 / night

                                                            £390 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 2 hours 5 minutes

                                                            from £86 / night

                                                            Distance approx 14.86 miles from Chepstow

                                                              8

                                                              Holiday b&b in Pucklechurch

                                                              Gloucestershire / Pucklechurch

                                                              1 2 1 night min

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • 1 night min

                                                              from £79 / night

                                                              £487 / week

                                                              Book View

                                                              from £79 / night

                                                              Distance approx 17.37 miles from Chepstow

                                                              (6) Excellent 

                                                                7

                                                                Nympsfield holiday barn rental

                                                                Gloucestershire / Nympsfield

                                                                2 4 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • min stay varies
                                                                • Child friendly
                                                                • Pet friendly

                                                                from £81 / night

                                                                £458 - £705 / week

                                                                Book View

                                                                from £81 / night

                                                                Distance approx 3.14 miles from Chepstow Show on Map

                                                                (63) Excellent 

                                                                Certificate of Excellence

                                                                  14

                                                                  Holiday cottage with indoor pool in Forest of Dean

                                                                  Gloucestershire / Forest of Dean

                                                                  2 4 3 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 4
                                                                  • 3 nights min
                                                                  • Nearest beach 60 km
                                                                  • Swimming pool
                                                                  • Child friendly

                                                                  Certificate of Excellence

                                                                  from £92 / night

                                                                  £630 - £871 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 1 hour 36 minutes

                                                                  from £92 / night

                                                                  Distance approx 13.51 miles from Chepstow

                                                                    9

                                                                    Holiday apartment rental

                                                                    England / Bristol

                                                                    1 4 2 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 4
                                                                    • 2 nights min
                                                                    • Child friendly
                                                                    • Car not necessary

                                                                    from £92 / night

                                                                    £573 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 2 hours 6 minutes

                                                                    from £92 / night

                                                                    Distance approx 11.15 miles from Chepstow

                                                                      17

                                                                      Holiday apartment in Weston-in-Gordano

                                                                      Portishead / Weston-in-Gordano

                                                                      2 5 1 night min

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

                                                                      from £138 / night

                                                                      £796 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 1 hour 19 minutes

                                                                      from £138 / night

                                                                      Distance approx 12.79 miles from Chepstow

                                                                        7

                                                                        Holiday apartment in Bristol

                                                                        England / Bristol

                                                                        1 2 2 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 2
                                                                        • 2 nights min
                                                                        • Ask owner if suitable for children

                                                                        from £63 / night

                                                                        £441 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 2 hours 47 minutes

                                                                        from £63 / night

                                                                        Distance approx 17.01 miles from Chepstow

                                                                        (4) Excellent 

                                                                          29

                                                                          Holiday barn in Tetbury

                                                                          Cotswolds / Tetbury

                                                                          1 2 min stay varies

                                                                          • 1 bedroom
                                                                          • sleeps 2
                                                                          • min stay varies
                                                                          • Private garden

                                                                          from £126 / night

                                                                          £516 - £687 / week

                                                                          Book View

                                                                          from £126 / night

                                                                          Distance approx 12.75 miles from Chepstow

                                                                          (3) Excellent 

                                                                          Certificate of Excellence

                                                                            9

                                                                            Holiday apartment with golf nearby in Bristol

                                                                            England / Bristol

                                                                            1 4 min stay varies

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • min stay varies
                                                                            • Nearest beach 40 km
                                                                            • Child friendly

                                                                            Certificate of Excellence

                                                                            from £92 / night

                                                                            £544 - £813 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 2 hours 19 minutes

                                                                            from £92 / night

                                                                            Distance approx 14.81 miles from Chepstow

                                                                            (6) Excellent 

                                                                            Certificate of Excellence

                                                                              9

                                                                              Holiday cottage in Symonds Yat

                                                                              Ross-on-Wye / Symonds Yat

                                                                              2 4 2 nights min

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

                                                                              Certificate of Excellence

                                                                              from £103 / night

                                                                              £504 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 2 hours 5 minutes

                                                                              from £103 / night

                                                                              Distance approx 14.81 miles from Chepstow

                                                                              (5) Excellent 

                                                                              Certificate of Excellence

                                                                                6

                                                                                Holiday cottage in Symonds Yat

                                                                                Ross-on-Wye / Symonds Yat

                                                                                2 4 2 nights min

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

                                                                                Certificate of Excellence

                                                                                from £103 / night

                                                                                £504 / week

                                                                                Book View

                                                                                Responds fast!
                                                                                avg. 2 hours 5 minutes

                                                                                from £103 / night

                                                                                Distance approx 16.02 miles from Chepstow

                                                                                  15

                                                                                  Frampton on Severn holiday cottage rental

                                                                                  Cotswolds / Frampton on Severn

                                                                                  2 4 2 nights min

                                                                                  • 2 bedrooms
                                                                                  • sleeps 4
                                                                                  • 2 nights min
                                                                                  • Nearest beach 75 km
                                                                                  • Child friendly
                                                                                  • Pet friendly

                                                                                  from £338 / night

                                                                                  £2,061 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 2 hours 35 minutes

                                                                                  from £338 / night

                                                                                  Top Destination reviews

                                                                                  Spring Cottage
                                                                                  A beautiful find

                                                                                  I don't normally write reviews but felt I needed to. My friend and I booked this cottage as our yearly pre-summer holiday break...the wind down before having the kids at home for 6 weeks. We normally do Clovelly which we adore but I felt like a change. The drive to the cottage instantly relaxed you, down a lane that only fits one car but with properties and views so quaint I felt miles from all the world's stresses. We arrived at the gorgeous cottage and I have to say the photos on here are true to size. It was lovely to arrive to real coffee, fresh eggs and homemade bread. The little cottage garden with the willow Tree had a lovely bistro set underneath, and eating breakfast there in the mornings was a dream. It was so quiet...Yes the owners live in the house opposite, however you don't notice it and it's not overlooking you or intrusive. The walks were stunning. We walked up the steep hill through the woods, back along the river, through fields with horses...the amazing walk to tintern abbey down the old railway track, along the river, a pint in the local pub...it was truly a relaxing find a million miles from anywhere.... We both felt it was great value and beautifully done. Only wish we had longer to do more of the walks on offer.see more
                                                                                  Maes-y-Felin Monmouthshire farmstay cottage- 46322
                                                                                  Great place

                                                                                  I just needed somewhere to stay that was convenient for events in Abergavenny and Blaenavon but not too remote. This cottage was perfect for this. The facilities were great and we made full use of them. I cannot fault the cottage and we were made most welcome. I would love to go back and would recommend it to anyonesee more
                                                                                  The Welsh Gatehouse (Book for more nights and the price will decrease)
                                                                                  Magic. We just loved it....

                                                                                  We had a fantastic and really memorable stay. To say that it is unique is just not doing it justice, as it is sooooo romantic and so cosy that we would love to be there every weekend. We had intended to do lot's of sightseeing, but we found it hard to tear ourselves away from the place. The stairs up are different, but what do you expect in what is a property / castle built over 500 years ago! Highly recommend visiting Tintern Abbey, the other side of Chepstow.see more
                                                                                  Oakgrove Cottage
                                                                                  Relaxing oasis!

                                                                                  Just what we needed, we have a 3 month old baby and just wanted somewhere we could totally chill without worrying about neighbours etc if he cried which obviously they do! We had everything we needed in the property, when we arrived Gina met us and showed us how everything worked and recommended a few places to go and eat. The accomodation was clean and well looked after and we felt relaxed as soon as we unpacked. We had a couple of days just relaxing and sunbathing but we ate out every night at the local pubs and everyone was so friendly especially at the Anchor the food was amazing too. If you want to do lots there are plenty of places to visit and lots of walks but if you just want a lazy time like us then the accomodation suits that too as there is a lovely patio area where you can just relax and at nightime watch the local wildlife, we had a badger come right up to the window. Overall a total oasis from the busy city!see more

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