HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit

Make a vacation rental in Berkshires, USA your home away from home

The Berkshires are a range of hills in Northwestern Massachusetts. Holidaymakers head for vacation rentals in the Berkshires to admire some lovely natural landscapes and take part if a host of outdoor activities, from walking to mountain biking and horseback riding. The region is also a key centre for the arts, with various important institutions located here.

Things to do in the Berkshires, USA

The region around Berkshires vacation accommodation is first and foremost a destination for outdoor activities. The world-famous Appalachian Trail runs through here, and there is also a huge network of other trails to explore taking walkers through expanses rich in natural beauty. A highlight is Mount Washington, a pretty town with easy access to the eponymous State Park. Nearby Bash Bish Falls, the highest waterfall in the state is found in this area.

In summer around Berkshire accommodation you could make the most of the region’s rivers, going on a fishing or rafting trip. On land you could head for one of the area’s many excellent golf courses. Great choices would be Berkshire Hills Country Club, Pontoosuc Lake, Wahconah, Bas Ridge, Skyline, Waubeeka, Taconic and Donnybrook.

Meanwhile in the winter, Berkshire vacation rentals are found in a good winter sport destination. Perhaps the most popular activity at this time of year is cross-country skiing, thanks to the numerous national parks, but there are also a number of resorts here, including Catamount, Bousquet and Jiminy Peak, which is the largest resort for ski and snowboard in the whole of New England.

Places to visit on holiday in Berkshires, USA

The City of Albany, in Upstate New York, is no more than an hour by car from Berkshires self-catering accommodation. It’s the capital of the state. And features New York’s Capitol with its elaborate architecture, as well as the Empire State Plaza, which is a venue for live music in the summer months. The New York State Museum is the largest of its kind in the country, and details the history of the state.

Weather in Berkshires, USA

On holiday at Berkshires vacation rentals you’ll be able to expect cold weather in winter, with temperatures slipping below freezing between November and March. There’s also quite a lot of snowfall on higher ground at this time of year. In summer there are warm conditions, from June to September.

Cheap flights to Berkshires, USA

If you head for Berkshires self-catering vacation accommodation from the UK, the most convenient way to get here would be to fly to Boston Logan International (BOS) from London Heathrow (LHR) with Delta, Virgin or British Airways, and then make the two hour drive across to Berkshire County.

  • Showing 1-50 of 300+
Additional service fee may apply.
  View Map Map
    avg/night
    • 2 BR
    • 1 BA
    • Sleeps 4
    Apartment #3752748
    4
    Viewed 33 times in the last 48 hours
      Wonderful! 4.8/5
      (38 reviews)
      avg/night
      • 2 BR
      • 2 BA
      • Sleeps 6
      Cottage #293009
      38
      Viewed 84 times in the last 48 hours
        Exceptional! 5.0/5
        (6 reviews)
        avg/night
        • 5 BR
        • 5 BA
        • Separate Toilet
        • Sleeps 10
        House #857164vb
        6
        Viewed 16 times in the last 48 hours
          avg/night
          • 2 BR
          • 2 BA
          • Sleeps 8
          Condo #907348vb
          0
          Viewed 53 times in the last 48 hours
            Wonderful! 4.8/5
            (23 reviews)
            avg/night
            • 1 BR
            • 1 BA
            • Sleeps 4
            House #310035vb
            23
            Viewed 15 times in the last 48 hours
              Exceptional! 5.0/5
              (25 reviews)
              avg/night
              • Studio
              • 1 BA
              • Sleeps 2
              Cottage #571465vb
              25
              Viewed 23 times in the last 48 hours
                avg/night
                • 2 BR
                • 2 BA
                • Sleeps 8
                Condo #4281302
                1
                Viewed 22 times in the last 48 hours
                  Wonderful! 4.9/5
                  (20 reviews)
                  avg/night
                  • 2 BR
                  • 1 BA
                  • Sleeps 5
                  Cottage #707780vb
                  20
                  Viewed 38 times in the last 48 hours
                    Exceptional! 5.0/5
                    (6 reviews)
                    avg/night
                    • 5 BR
                    • 3 BA
                    • Separate Toilet
                    • Sleeps 16
                    House #866131vb
                    6
                    Viewed 56 times in the last 48 hours
                      Exceptional! 5.0/5
                      (30 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 4
                      House #424508vb
                      30
                      Viewed 42 times in the last 48 hours
                        Wonderful! 4.8/5
                        (11 reviews)
                        avg/night
                        • 1 BR
                        • 1 BA
                        • Sleeps 4
                        Apartment #437137vb
                        11
                        Viewed 44 times in the last 48 hours
                          Exceptional! 5.0/5
                          (7 reviews)
                          avg/night
                          • 4 BR
                          • 3 BA
                          • Sleeps 8
                          House #585864vb
                          7
                          Viewed 34 times in the last 48 hours
                            Exceptional! 5.0/5
                            (9 reviews)
                            avg/night
                            • 3 BR
                            • 2 BA
                            • Separate Toilet
                            • Sleeps 8
                            House #854910vb
                            9
                            Viewed 16 times in the last 48 hours
                              Wonderful! 4.8/5
                              (19 reviews)
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 8
                              House #236935vb
                              19
                              Viewed 13 times in the last 48 hours
                                Exceptional! 5.0/5
                                (29 reviews)
                                avg/night
                                • 4 BR
                                • 3 BA
                                • Separate Toilet
                                • Sleeps 8
                                House #580967vb
                                29
                                Viewed 14 times in the last 48 hours
                                  Wonderful! 4.8/5
                                  (5 reviews)
                                  avg/night
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 6
                                  House #830744vb
                                  5
                                  Viewed 43 times in the last 48 hours
                                    Wonderful! 4.8/5
                                    (22 reviews)
                                    avg/night
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 5
                                    Cabin #189705vb
                                    22
                                    Viewed 36 times in the last 48 hours
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 8
                                      Condo #724286vb
                                      2
                                      Viewed 41 times in the last 48 hours
                                        Wonderful! 4.9/5
                                        (17 reviews)
                                        avg/night
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 6
                                        Cottage #300900
                                        17
                                        Viewed 50 times in the last 48 hours
                                          Exceptional! 5.0/5
                                          (14 reviews)
                                          avg/night
                                          • 6 BR
                                          • 5 BA
                                          • Sleeps 20
                                          Estate #4258796
                                          14
                                          Viewed 182 times in the last 48 hours
                                            Wonderful! 4.9/5
                                            (32 reviews)
                                            avg/night
                                            • 1 BR
                                            • 1 BA
                                            • Sleeps 3
                                            House #135474vb
                                            32
                                            Viewed 23 times in the last 48 hours
                                              Exceptional! 5.0/5
                                              (9 reviews)
                                              avg/night
                                              • 2 BR
                                              • 2 BA
                                              • Sleeps 6
                                              Cottage #3790476
                                              9
                                              Viewed 15 times in the last 48 hours
                                                Wonderful! 4.8/5
                                                (13 reviews)
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Separate Toilet
                                                • Sleeps 8
                                                House #607741vb
                                                13
                                                Viewed 37 times in the last 48 hours
                                                  Wonderful! 4.9/5
                                                  (15 reviews)
                                                  avg/night
                                                  • 6 BR
                                                  • 6 BA
                                                  • Sleeps 12
                                                  Estate #568397vb
                                                  15
                                                  Viewed 33 times in the last 48 hours
                                                    Wonderful! 4.9/5
                                                    (15 reviews)
                                                    avg/night
                                                    • 2 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    House #3720156
                                                    15
                                                    Viewed 15 times in the last 48 hours
                                                      Excellent! 4.6/5
                                                      (48 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 1 BA
                                                      • Sleeps 4
                                                      Cabin #182224
                                                      48
                                                      Viewed 52 times in the last 48 hours
                                                        Excellent! 4.4/5
                                                        (11 reviews)
                                                        avg/night
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 4
                                                        House #3860654
                                                        11
                                                        Viewed 31 times in the last 48 hours
                                                          avg/night
                                                          • 3 BR
                                                          • 1 BA
                                                          • Separate Toilet
                                                          • Sleeps 6
                                                          House #4272947
                                                          3
                                                          Viewed 15 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (17 reviews)
                                                            avg/night
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            House #3893831
                                                            17
                                                            Viewed 34 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (23 reviews)
                                                              avg/night
                                                              • 5 BR
                                                              • 5 BA
                                                              • Sleeps 12
                                                              House #729783vb
                                                              23
                                                              Viewed 16 times in the last 48 hours
                                                                Wonderful! 4.9/5
                                                                (36 reviews)
                                                                avg/night
                                                                • 3 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                House #469617vb
                                                                36
                                                                Viewed 30 times in the last 48 hours
                                                                  Excellent! 4.6/5
                                                                  (11 reviews)
                                                                  avg/night
                                                                  • 4 BR
                                                                  • 1 BA
                                                                  • Separate Toilet
                                                                  • Sleeps 8
                                                                  House #467696vb
                                                                  11
                                                                  Viewed 19 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (5 reviews)
                                                                    avg/night
                                                                    • Studio
                                                                    • 1 BA
                                                                    • Sleeps 3
                                                                    Studio #846966vb
                                                                    5
                                                                    Viewed 33 times in the last 48 hours
                                                                      Exceptional! 5.0/5
                                                                      (16 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 1 BA
                                                                      • Separate Toilet
                                                                      • Sleeps 8
                                                                      House #3811779
                                                                      16
                                                                      Viewed 26 times in the last 48 hours
                                                                        Excellent! 4.7/5
                                                                        (10 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 1 BA
                                                                        • Separate Toilet
                                                                        • Sleeps 6
                                                                        Chateau / Country House #4149878
                                                                        10
                                                                        Viewed 55 times in the last 48 hours
                                                                          • 3 BR
                                                                          • 1 BA
                                                                          • Sleeps 6
                                                                          Apartment #901029vb
                                                                          1
                                                                            Wonderful! 4.9/5
                                                                            (14 reviews)
                                                                            avg/night
                                                                            • 5 BR
                                                                            • 3 BA
                                                                            • Sleeps 10
                                                                            House #603552vb
                                                                            14
                                                                            Viewed 36 times in the last 48 hours
                                                                              Excellent! 4.7/5
                                                                              (22 reviews)
                                                                              avg/night
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 6
                                                                              Condo #3471790
                                                                              22
                                                                              Viewed 12 times in the last 48 hours
                                                                                Wonderful! 4.8/5
                                                                                (16 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 10
                                                                                House #601571vb
                                                                                16
                                                                                Viewed 39 times in the last 48 hours
                                                                                  Excellent! 4.7/5
                                                                                  (27 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 8
                                                                                  House #419897vb
                                                                                  27
                                                                                  Viewed 37 times in the last 48 hours
                                                                                    Wonderful! 4.8/5
                                                                                    (5 reviews)
                                                                                    avg/night
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 7
                                                                                    House #774024vb
                                                                                    5
                                                                                    Viewed 21 times in the last 48 hours
                                                                                      Wonderful! 4.8/5
                                                                                      (23 reviews)
                                                                                      avg/night
                                                                                      • 7 BR
                                                                                      • 4 BA
                                                                                      • Sleeps 10
                                                                                      Farmhouse #444851vb
                                                                                      23
                                                                                      Viewed 39 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (9 reviews)
                                                                                        avg/night
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        House #892478vb
                                                                                        9
                                                                                        Viewed 49 times in the last 48 hours
                                                                                          Exceptional! 5.0/5
                                                                                          (16 reviews)
                                                                                          avg/night
                                                                                          • 6 BR
                                                                                          • 5 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 16
                                                                                          House #396147vb
                                                                                          16
                                                                                          Viewed 57 times in the last 48 hours
                                                                                            Exceptional! 5.0/5
                                                                                            (26 reviews)
                                                                                            avg/night
                                                                                            • 2 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            Condo #651723vb
                                                                                            26
                                                                                            Viewed 26 times in the last 48 hours
                                                                                              avg/night
                                                                                              • 3 BR
                                                                                              • 4 BA
                                                                                              • Sleeps 10
                                                                                              Chateau / Country House #856467vb
                                                                                              4
                                                                                              Viewed 29 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (11 reviews)
                                                                                                avg/night
                                                                                                • 3 BR
                                                                                                • 2 BA
                                                                                                • Sleeps 6
                                                                                                House #471229vb
                                                                                                11
                                                                                                Viewed 7 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (14 reviews)
                                                                                                  avg/night
                                                                                                  • 5 BR
                                                                                                  • 2 BA
                                                                                                  • Separate Toilet
                                                                                                  • Sleeps 10
                                                                                                  Barn #616214vb
                                                                                                  14
                                                                                                  Viewed 53 times in the last 48 hours
                                                                                                    Exceptional! 5.0/5
                                                                                                    (8 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Separate Toilet
                                                                                                    • Sleeps 6
                                                                                                    House #4153058
                                                                                                    8
                                                                                                    Viewed 12 times in the last 48 hours
                                                                                                      Wonderful! 4.8/5
                                                                                                      (24 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 6
                                                                                                      Condo #238631vb
                                                                                                      24
                                                                                                      Viewed 15 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+