Houses in West Stockbridge and Apartments – Holiday Lettings - Holiday Rentals West Stockbridge

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

145 Holiday homes

    5

    West Stockbridge holiday condo rental

    Berkshires / West Stockbridge

    2 6 1 night min

    • 2 bedrooms
    • sleeps 6
    • 1 night min
    • Child friendly
    • Air conditioning
    • Pet friendly

    from £216 / night

    £1,251 / week

    Book View

    Responds fast!
    avg. 1 hour 18 minutes

    from £216 / night

    (4) Excellent 

      10

      Farmhouse rental in West Stockbridge

      Berkshires / West Stockbridge

      5 12 2 nights min

      • 5 bedrooms
      • sleeps 12
      • 2 nights min
      • Beach / lakeside relaxation
      • Child friendly
      • Air conditioning

      from £282 / night

      £1,971 / week

      Book View

      from £282 / night

      (7) Excellent 

        18

        West Stockbridge holiday home rental

        Berkshires / West Stockbridge

        3 8 min stay varies

        • 3 bedrooms
        • sleeps 8
        • min stay varies
        • Beach / lakeside relaxation
        • Child friendly
        • Pet friendly

        from £305 / night

        £2,004 / week

        Book View

        from £305 / night

        (2) Excellent 

          8

          Apartment rental in West Stockbridge

          Berkshires / West Stockbridge

          2 6 1 night min

          • 2 bedrooms
          • sleeps 6
          • 1 night min
          • Ask owner if suitable for children
          • Air conditioning
          • Ask about pets

          from £87 / night

          £741 / week

          Book View

          Responds fast!
          avg. 1 hour 18 minutes

          from £87 / night

          (1) Excellent 

            24

            Ski home to rent in West Stockbridge

            Berkshires / West Stockbridge

            2 4 min stay varies

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

            from £144 / night

            £1,006 / week

            Book View

            Responds fast!
            avg. 9 minutes

            from £144 / night

            (39) Excellent 

              20

              Holiday home rental

              Berkshires / West Stockbridge

              5 12 min stay varies

              • 5 bedrooms
              • sleeps 12
              • min stay varies
              • Nearest beach 2 km
              • Child friendly
              • Pet friendly

              from £225 / night

              £1,338 - £2,244 / week

              Book View

              from £225 / night

                16

                Holiday b&b in West Stockbridge

                Berkshires / West Stockbridge

                2 4 2 nights min

                • 2 bedrooms
                • sleeps 4
                • 2 nights min
                • Air conditioning
                • Private garden

                from £182 / night

                £1,273 / week

                Book View

                from £182 / night

                Great rentals within 20 miles that match your search

                Distance approx 12.24 miles from West Stockbridge

                (4) Excellent 

                  24

                  Ski cottage to rent in New Marlborough

                  Berkshires / New Marlborough

                  2 4 min stay varies

                  • 2 bedrooms
                  • sleeps 4
                  • min stay varies
                  • Ski

                  from £156 / night

                  £1,092 / week

                  Book View

                  Responds fast!
                  avg. 36 minutes

                  from £156 / night

                  Distance approx 14.24 miles from West Stockbridge

                    32

                    Ski home to rent in Monterey

                    Berkshires / Monterey

                    4 12 min stay varies

                    • 4 bedrooms
                    • sleeps 12
                    • min stay varies
                    • Ski
                    • Child friendly
                    • Air conditioning

                    from £260 / night

                    £1,819 / week

                    Book View

                    Responds fast!
                    avg. 36 minutes

                    from £260 / night

                    Distance approx 16.98 miles from West Stockbridge

                    (13) Very Good 

                      13

                      Holiday home in Becket

                      Berkshires / Becket

                      2 4 2 nights min

                      • 2 bedrooms
                      • sleeps 4
                      • 2 nights min
                      • Child friendly
                      • Air conditioning
                      • Ask about pets

                      from £129 / night

                      £862 / week

                      Book View

                      from £129 / night

                      Distance approx 17.52 miles from West Stockbridge

                      (2) Excellent 

                        14

                        Holiday home in Copake

                        New York / Copake

                        3 5 3 nights min

                        • 3 bedrooms
                        • sleeps 5
                        • 3 nights min
                        • Beach / lakeside relaxation
                        • Nearest beach 0 km
                        • Child friendly

                        from £173 / night

                        £1,251 / week

                        Book View

                        Responds fast!
                        avg. 2 hours 41 minutes

                        from £173 / night

                        Distance approx 4.67 miles from West Stockbridge Show on Map

                        (1) Excellent 

                          17

                          Holiday home in Stockbridge

                          Berkshires / Stockbridge

                          2 6 7 nights min

                          • 2 bedrooms
                          • sleeps 6
                          • 7 nights min
                          • Child friendly
                          • Air conditioning
                          • Private garden

                          from £186 / night

                          £1,299 / week

                          Book View

                          from £186 / night

                          Distance approx 11.58 miles from West Stockbridge

                            31

                            Pittsfield holiday home rental

                            Berkshires / Pittsfield

                            7 18 2 nights min

                            • 7 bedrooms
                            • sleeps 18
                            • 2 nights min
                            • Child friendly
                            • Ask about pets

                            from £266 / night

                            £1,951 / week

                            Book View

                            from £266 / night

                            Distance approx 13 miles from West Stockbridge

                            (1) Excellent 

                              21

                              Old Chatham holiday home rental

                              New York / Old Chatham

                              2 4 2 nights min

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

                              from £130 / night

                              £910 / week

                              Book View

                              from £130 / night

                              Distance approx 9.21 miles from West Stockbridge

                              (4) Excellent 

                                30

                                Holiday home in Great Barrington

                                Berkshires / Great Barrington

                                5 12 2 nights min

                                • 5 bedrooms
                                • sleeps 12
                                • 2 nights min
                                • Nearest beach 0.32 km
                                • Child friendly
                                • Air conditioning

                                from £260 / night

                                £2,295 - £3,023 / week

                                Book View

                                from £260 / night

                                Distance approx 12.84 miles from West Stockbridge

                                  23

                                  Holiday home in Monterey

                                  Berkshires / Monterey

                                  4 10 3 nights min

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

                                  from £355 / night

                                  £2,482 / week

                                  Book View

                                  from £355 / night

                                  Distance approx 9.56 miles from West Stockbridge

                                  (1) Excellent 

                                    10

                                    Tyringham holiday cottage rental

                                    Berkshires / Tyringham

                                    1 2 2 nights min

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

                                    from £195 / night

                                    £1,364 / week

                                    Book View

                                    Responds fast!
                                    avg. 1 hour 29 minutes

                                    from £195 / night

                                    Distance approx 9.6 miles from West Stockbridge

                                      48

                                      Holiday home in Hillsdale

                                      New York / Hillsdale

                                      5 14 2 nights min

                                      • 5 bedrooms
                                      • sleeps 14
                                      • 2 nights min
                                      • Ask owner if suitable for children

                                      from £518 / night

                                      £3,926 - £5,738 / week

                                      Book View

                                      from £518 / night

                                      Distance approx 17.14 miles from West Stockbridge

                                        22

                                        Holiday home in Otis

                                        Berkshires / Otis

                                        6 14 7 nights min

                                        • 6 bedrooms
                                        • sleeps 14
                                        • 7 nights min
                                        • Ask owner if suitable for children
                                        • Ask about pets

                                        from £518 / night

                                        £3,624 - £4,832 / week

                                        Book View

                                        from £518 / night

                                        Distance approx 5.53 miles from West Stockbridge Show on Map

                                        (4) Excellent 

                                          18

                                          Holiday home with golf nearby in Lee

                                          Berkshires / Lee

                                          5 9 7 nights min

                                          • 5 bedrooms
                                          • sleeps 9
                                          • 7 nights min
                                          • Beach / lakeside relaxation
                                          • Child friendly
                                          • Air conditioning

                                          from £619 / night

                                          £4,330 / week

                                          Book View

                                          from £619 / night

                                          Distance approx 15.53 miles from West Stockbridge

                                            19

                                            Holiday home in Philmont

                                            New York / Philmont

                                            3 4 2 nights min

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

                                            from £169 / night

                                            £1,126 / week

                                            Book View

                                            from £169 / night

                                            Distance approx 9.52 miles from West Stockbridge

                                              32

                                              North Egremont holiday private room rental

                                              Berkshires / North Egremont

                                              1 2 1 night min

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

                                              from £130 / night

                                              £910 / week

                                              Book View

                                              Responds fast!
                                              avg. 33 minutes

                                              from £130 / night

                                              Distance approx 11.15 miles from West Stockbridge

                                                12

                                                Monterey holiday home rental

                                                Berkshires / Monterey

                                                7 21 nights min

                                                • sleeps 7
                                                • 21 nights min
                                                • Ask owner if suitable for children
                                                • Car not necessary
                                                • Ask about pets

                                                from £154 / night

                                                £1,079 / week

                                                Book View

                                                from £154 / night

                                                Distance approx 16.79 miles from West Stockbridge

                                                (1) Excellent 

                                                  26

                                                  Holiday home in Hancock

                                                  Berkshires / Hancock

                                                  4 8 1 night min

                                                  • 4 bedrooms
                                                  • sleeps 8
                                                  • 1 night min
                                                  • Child friendly
                                                  • Private garden

                                                  from £74 / night

                                                  £465 - £974 / week

                                                  Book View

                                                  from £74 / night

                                                  Distance approx 8.74 miles from West Stockbridge

                                                    10

                                                    Holiday b&b in Lee

                                                    Berkshires / Lee

                                                    1 2 2 nights min

                                                    • 1 bedroom
                                                    • sleeps 2
                                                    • 2 nights min
                                                    • Nearest beach 5 km
                                                    • Ask owner if suitable for children
                                                    • Ask about pets

                                                    from £69 / night

                                                    £607 - £758 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 36 minutes

                                                    from £69 / night

                                                    Distance approx 8.68 miles from West Stockbridge

                                                    (1) Excellent 

                                                      8

                                                      Holiday b&b in Lee

                                                      Berkshires / Lee

                                                      1 2 2 nights min

                                                      • 1 bedroom
                                                      • sleeps 2
                                                      • 2 nights min
                                                      • Nearest beach 8 km
                                                      • Ask owner if suitable for children
                                                      • Air conditioning

                                                      from £156 / night

                                                      £798 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 36 minutes

                                                      from £156 / night

                                                      Distance approx 2.75 miles from West Stockbridge Show on Map

                                                      (1) Excellent 

                                                        24

                                                        Holiday cottage in Stockbridge

                                                        Berkshires / Stockbridge

                                                        2 4 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • min stay varies
                                                        • Air conditioning

                                                        from £259 / night

                                                        £1,813 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 12 minutes

                                                        from £259 / night

                                                        Distance approx 9.56 miles from West Stockbridge

                                                          9

                                                          Tyringham holiday home rental

                                                          Berkshires / Tyringham

                                                          1 4 2 nights min

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

                                                          from £217 / night

                                                          £1,299 - £1,906 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 1 hour 29 minutes

                                                          from £217 / night

                                                          Distance approx 14.63 miles from West Stockbridge

                                                            13

                                                            Holiday condo in Hancock

                                                            Berkshires / Hancock

                                                            3 6 30 nights min

                                                            • 3 bedrooms
                                                            • sleeps 6
                                                            • 30 nights min
                                                            • Swimming pool
                                                            • Child friendly
                                                            • Air conditioning

                                                            from £216 / night

                                                            £1,510 / week

                                                            Book View

                                                            from £216 / night

                                                            Distance approx 5.1 miles from West Stockbridge

                                                              9

                                                              Canaan holiday cottage rental

                                                              New York / Canaan

                                                              1 2 7 nights min

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • 7 nights min
                                                              • Beach / lakeside relaxation
                                                              • Nearest beach 2 km
                                                              • Air conditioning

                                                              from £87 / night

                                                              £607 / week

                                                              Book View

                                                              from £87 / night

                                                              Distance approx 2.43 miles from West Stockbridge Show on Map

                                                                19

                                                                Stockbridge holiday home rental

                                                                Berkshires / Stockbridge

                                                                4 10 2 nights min

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

                                                                from £604 / night

                                                                £2,114 - £3,564 / week

                                                                Book View

                                                                from £604 / night

                                                                Distance approx 6.25 miles from West Stockbridge Show on Map

                                                                  15

                                                                  Holiday private room accommodation

                                                                  Berkshires / Lee

                                                                  1 1 1 night min

                                                                  • 1 bedroom
                                                                  • sleeps 1
                                                                  • 1 night min
                                                                  • Beach / lakeside relaxation
                                                                  • Nearest beach 3 km

                                                                  from £58 / night

                                                                  £109 / week

                                                                  Book View

                                                                  from £58 / night

                                                                  Distance approx 13 miles from West Stockbridge

                                                                    19

                                                                    Old Chatham holiday villa rental

                                                                    New York / Old Chatham

                                                                    2 4 2 nights min

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

                                                                    from £147 / night

                                                                    £1,027 / week

                                                                    Book View

                                                                    from £147 / night

                                                                    Distance approx 16.34 miles from West Stockbridge

                                                                    (3) Very Good 

                                                                      25

                                                                      Holiday home rental

                                                                      New York / Valatie

                                                                      3 5 7 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 5
                                                                      • 7 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Child friendly
                                                                      • Air conditioning

                                                                      from £216 / night

                                                                      £1,507 / week

                                                                      Book View

                                                                      from £216 / night

                                                                      Distance approx 19.18 miles from West Stockbridge

                                                                      (1) Very Good 

                                                                        4

                                                                        Holiday home in Hancock

                                                                        Berkshires / Hancock

                                                                        2 4 2 nights min

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

                                                                        from £2,157 / night

                                                                        £25,848 / week

                                                                        Book View

                                                                        from £2,157 / night

                                                                        Distance approx 10.2 miles from West Stockbridge

                                                                          21

                                                                          Holiday home rental

                                                                          Berkshires / Great Barrington

                                                                          4 12 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 12
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child friendly
                                                                          • Air conditioning

                                                                          from £497 / night

                                                                          £3,473 / week

                                                                          Book View

                                                                          from £497 / night

                                                                          Distance approx 15.77 miles from West Stockbridge

                                                                          (1) Very Good 

                                                                            6

                                                                            Hancock holiday apartment let

                                                                            Berkshires / Hancock

                                                                            2 6 1 night min

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

                                                                            from £222 / night

                                                                            £1,330 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 16 minutes

                                                                            from £222 / night

                                                                            Distance approx 15.94 miles from West Stockbridge

                                                                              8

                                                                              Holiday condo with shared pool in Hancock

                                                                              Berkshires / Hancock

                                                                              2 8 7 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 8
                                                                              • 7 nights min
                                                                              • Swimming pool
                                                                              • Child friendly
                                                                              • Air conditioning

                                                                              from £178 / night

                                                                              £1,241 / week

                                                                              Book View

                                                                              from £178 / night

                                                                              Distance approx 8.77 miles from West Stockbridge

                                                                                14

                                                                                Holiday home in Spencertown

                                                                                New York / Spencertown

                                                                                2 6 30 nights min

                                                                                • 2 bedrooms
                                                                                • sleeps 6
                                                                                • 30 nights min
                                                                                • Beach / lakeside relaxation
                                                                                • Child friendly
                                                                                • Air conditioning

                                                                                from £116 / night

                                                                                £809 / week

                                                                                Book View

                                                                                from £116 / night

                                                                                Distance approx 14.43 miles from West Stockbridge

                                                                                  17

                                                                                  New Marlborough holiday home rental

                                                                                  Berkshires / New Marlborough

                                                                                  4 7 min stay varies

                                                                                  • 4 bedrooms
                                                                                  • sleeps 7
                                                                                  • min stay varies
                                                                                  • Child friendly
                                                                                  • Private garden

                                                                                  from £130 / night

                                                                                  £768 / week

                                                                                  Book View

                                                                                  from £130 / night

                                                                                  Also consider