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A holiday rental home in Sheffield, Massachusetts is a wonderful choice for your next breakaway to the northern United States

There is something for everyone to enjoy when you choose Sheffield for a breakaway. A holiday rental home in Sheffield will put you close to all of the most popular activities and attractions in the Berkshires.

Things to Do on Holiday to Sheffield, Massachusetts

Whether you visit during the summer or the winter months you will find that there are many activities to enjoy. During the winter the activities include skiing, snowboarding, snowshoe treks and ice skating. Ski lessons and equipment rental are available. The spring and summer bring the opportunity for hiking, cycling, golf, boating and fishing. Visit nearby wineries to participate in a wine tasting or make a stop to a spa for a bit of pampering.

Places to Visit on Holiday to Sheffield, Massachusetts

Dozens of interesting attractions are located in and near Sheffield. Museums and lovely outdoor spots are amongst the offerings. The Emily Dickinson Museum and the Norman Rockwell Museum are each attractions dedicated to the work of a specific artist or writer. At these museums you can learn about the lives of the writer and artist and, at the Rockwell Museum, see examples of his work. Other museums are the Animajic Museum of Animation, Special Effects and Art, the Berkshire Scenic Railway Museum and the Bidwell House Museum. The Bidwell House Museum is the former home of a colonial era preacher. Here you can learn about what daily life was like during that time period. The Ashley House is another must-see for anyone interested in history. It was here that a slave made a decision to sue her owners for her freedom. The Appalachian Trail and the Ashuwillticook Rail Trails both offer gorgeous hiking and cycling trails as well as the chance to spot a variety of birds and other wildlife.

Weather in Sheffield, Massachusetts

Very cold winters and warm, pleasant summers are what you can expect when you holiday to Sheffield. The average low temperatures during the winter months are between -12° and -2° C and the average highs are 1° to 7° C. During the spring the average lows are between 6° and 11° C and the average spring highs are between 13° to 20° C. In the summer, the average lows are 11° to 13° C and the highs are 24° to 27° C. There is between 80 and 127 mm of snow or rain per month.

Travel to Sheffield, Massachusetts

The nearest airport to Sheffield is Bradley International Airport (BDL) which is 49 km away. Another option is Albany International Airport (ALB) which is 68 km from Sheffield. You will need a car for use during your stay.

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  • 1 - 50 of 300+
Additional service fee may apply.
    Exceptional! 5.0/5
    (52 reviews)
    avg/night
    • 4 BR
    • 3 BA
    • Sleeps 9
    House #95599vb
    52
    Viewed 9 times in the last 48 hours
      Exceptional! 5.0/5
      (29 reviews)
      avg/night
      • 3 BR
      • 2 BA
      • Sleeps 4
      House #424508vb
      29
      Viewed 39 times in the last 48 hours
        Excellent! 4.6/5
        (15 reviews)
        avg/night
        • 2 BR
        • 1 BA
        • Sleeps 4
        Cottage #373357vb
        15
        Viewed 10 times in the last 48 hours
          Wonderful! 4.9/5
          (21 reviews)
          avg/night
          • 3 BR
          • 2 BA
          • Separate Toilet
          • Sleeps 8
          House #332864vb
          21
            Wonderful! 4.8/5
            (48 reviews)
            avg/night
            • 2 BR
            • 1 BA
            • Sleeps 5
            Cabin #219964vb
            48
            Viewed 13 times in the last 48 hours
              Exceptional! 5.0/5
              (5 reviews)
              avg/night
              • 5 BR
              • 3 BA
              • Separate Toilet
              • Sleeps 16
              House #866131vb
              5
              Viewed 5 times in the last 48 hours
                Exceptional! 5.0/5
                (18 reviews)
                avg/night
                • 3 BR
                • 3 BA
                • Sleeps 9
                Farmhouse #710105vb
                18
                Viewed 8 times in the last 48 hours
                  Wonderful! 4.9/5
                  (11 reviews)
                  avg/night
                  • 4 BR
                  • 3 BA
                  • Sleeps 15
                  House #512619vb
                  11
                  Viewed 20 times in the last 48 hours
                    Exceptional! 5.0/5
                    (7 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Sleeps 6
                    House #384153
                    7
                      • 5 BR
                      • 2 BA
                      • Separate Toilet
                      • Sleeps 11
                      House #577344vb
                      2
                        Wonderful! 4.9/5
                        (14 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • Separate Toilet
                        • Sleeps 6
                        Barn #179027
                        14
                        Viewed 17 times in the last 48 hours
                          Wonderful! 4.9/5
                          (18 reviews)
                          avg/night
                          • 3 BR
                          • 2 BA
                          • Sleeps 8
                          House #211271
                          18
                            • 3 BR
                            • 2 BA
                            • Separate Toilet
                            • Sleeps 8
                            House #497959vb
                            4
                            Viewed 14 times in the last 48 hours
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              House #719709vb
                              1
                              Viewed 9 times in the last 48 hours
                                • 1 BR
                                • 1 BA
                                • Sleeps 2
                                Apartment #766104vb
                                2
                                  avg/night
                                  • 3 BR
                                  • 1 BA
                                  • Separate Toilet
                                  • Sleeps 6
                                  House #3893807
                                  1
                                  Viewed 12 times in the last 48 hours
                                    • 2 BR
                                    • 2 BA
                                    • Sleeps 8
                                    House #124299
                                      • 4 BR
                                      • 3 BA
                                      • Separate Toilet
                                      • Sleeps 10
                                      Chateau / Country House #464637vb
                                      2
                                      Viewed 8 times in the last 48 hours
                                        • 3 BR
                                        • 2 BA
                                        • Separate Toilet
                                        • Sleeps 6
                                        House #3558842
                                        1
                                          avg/night
                                          • 4 BR
                                          • 3 BA
                                          • Separate Toilet
                                          • Sleeps 10
                                          House #772872vb
                                          Viewed 16 times in the last 48 hours
                                            • 2 BR
                                            • 2 BA
                                            • Separate Toilet
                                            • Sleeps 8
                                            House #104868
                                            4
                                              Exceptional! 5.0/5
                                              (5 reviews)
                                              avg/night
                                              • 4 BR
                                              • 2 BA
                                              • Sleeps 8
                                              Chateau / Country House #4021614
                                              5
                                              Viewed 5 times in the last 48 hours
                                                avg/night
                                                • 3 BR
                                                • 2 BA
                                                • Separate Toilet
                                                • Sleeps 6
                                                House #4317148
                                                1
                                                Viewed 10 times in the last 48 hours
                                                  • 3 BR
                                                  • 3 BA
                                                  • Sleeps 10
                                                  House #575213vb
                                                    avg/night
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 6
                                                    House #953681vb
                                                    Viewed 5 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (21 reviews)
                                                      • 4 BR
                                                      • 3 BA
                                                      • Separate Toilet
                                                      • Sleeps 8
                                                      Chateau / Country House #396464vb
                                                      21
                                                      Viewed 9 times in the last 48 hours
                                                        • 4 BR
                                                        • 4 BA
                                                        • Sleeps 10
                                                        House #453690vb
                                                        8
                                                          Exceptional! 5.0/5
                                                          (6 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          House #804956vb
                                                          6
                                                          Viewed 10 times in the last 48 hours
                                                            Exceptional! 5.0/5
                                                            (12 reviews)
                                                            avg/night
                                                            • 6 BR
                                                            • 5 BA
                                                            • Sleeps 20
                                                            Estate #4258796
                                                            12
                                                            Viewed 86 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (9 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 7
                                                              House #330190
                                                              9
                                                                Exceptional! 5.0/5
                                                                (71 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                Cottage #216065
                                                                71
                                                                Viewed 55 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (17 reviews)
                                                                  avg/night
                                                                  • 6 BR
                                                                  • 4 BA
                                                                  • Separate Toilet
                                                                  • Sleeps 12
                                                                  Estate #629154vb
                                                                  17
                                                                  Viewed 6 times in the last 48 hours
                                                                    Exceptional! 5.0/5
                                                                    (5 reviews)
                                                                    avg/night
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 2
                                                                    Apartment #735097vb
                                                                    5
                                                                      Exceptional! 5.0/5
                                                                      (7 reviews)
                                                                      avg/night
                                                                      • 5 BR
                                                                      • 4 BA
                                                                      • Separate Toilet
                                                                      • Sleeps 12
                                                                      Chateau / Country House #777079vb
                                                                      7
                                                                      Viewed 20 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (32 reviews)
                                                                        avg/night
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 8
                                                                        House #406592vb
                                                                        32
                                                                        Viewed 8 times in the last 48 hours
                                                                          Wonderful! 4.9/5
                                                                          (18 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 5
                                                                          Cottage #707780vb
                                                                          18
                                                                          Viewed 26 times in the last 48 hours
                                                                            Excellent! 4.6/5
                                                                            (48 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            Cabin #182224
                                                                            48
                                                                            Viewed 21 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (8 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • Sleeps 6
                                                                              House #572212vb
                                                                              8
                                                                              Viewed 6 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (21 reviews)
                                                                                avg/night
                                                                                • 5 BR
                                                                                • 5 BA
                                                                                • Sleeps 12
                                                                                House #729783vb
                                                                                21
                                                                                  Wonderful! 4.8/5
                                                                                  (37 reviews)
                                                                                  avg/night
                                                                                  • 2 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  Cottage #293009
                                                                                  37
                                                                                  Viewed 33 times in the last 48 hours
                                                                                    Exceptional! 5.0/5
                                                                                    (9 reviews)
                                                                                    avg/night
                                                                                    • 6 BR
                                                                                    • 3 BA
                                                                                    • Sleeps 10
                                                                                    House #4064007
                                                                                    9
                                                                                    Viewed 15 times in the last 48 hours
                                                                                      Excellent! 4.7/5
                                                                                      (9 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 7
                                                                                      House #997342
                                                                                      9
                                                                                      Viewed 11 times in the last 48 hours
                                                                                        • 2 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        Cottage #3790476
                                                                                        9
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 8
                                                                                          Farmhouse #3765427
                                                                                          7
                                                                                            Exceptional! 5.0/5
                                                                                            (29 reviews)
                                                                                            avg/night
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 6
                                                                                            Chalet #170905
                                                                                            29
                                                                                            Viewed 21 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (22 reviews)
                                                                                              avg/night
                                                                                              • 1 BR
                                                                                              • 1 BA
                                                                                              • Sleeps 5
                                                                                              Cabin #189705vb
                                                                                              22
                                                                                              Viewed 8 times in the last 48 hours
                                                                                                Wonderful! 4.9/5
                                                                                                (32 reviews)
                                                                                                avg/night
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 2
                                                                                                Apartment #3591655
                                                                                                32
                                                                                                Viewed 21 times in the last 48 hours
                                                                                                  Exceptional! 5.0/5
                                                                                                  (46 reviews)
                                                                                                  avg/night
                                                                                                  • 1 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 2
                                                                                                  Apartment #675472vb
                                                                                                  46
                                                                                                  Viewed 15 times in the last 48 hours
                                                                                                    Very Good! 4.0/5
                                                                                                    (8 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 7
                                                                                                    House #344576vb
                                                                                                    8
                                                                                                    Viewed 14 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (37 reviews)
                                                                                                      avg/night
                                                                                                      • 6 BR
                                                                                                      • 5 BA
                                                                                                      • Sleeps 14
                                                                                                      House #470802vb
                                                                                                      37
                                                                                                      Viewed 47 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+
                                                                                                       

                                                                                                      Recent Reviews

                                                                                                      Home away from Home..comfy and cozy

                                                                                                      5 of 5
                                                                                                      Our family spent Christmas at this wonderful house. It is a perfect place to create memories in the Berkshires. Close to Butternut and Bish Bash Falls. We hiked to the falls and it was wonderful. The house is comfy and cozy well equipped with everything you need for a great stay. The cherrry floors in the bedrooms are just beautiful. There is a gourmet kitchen with everything from top of the line pots and pans to every spice under the sun!! The owners even made our stay extra special by leaving a nice bottle of wine on the counter for us. How nice is that? We would highly reccommend this home. You will not want to leave on the day of your departure. We wish we were still there!! Thanks Edy and Chris. It was a 10 plus!!! We hope to come back soon!!
                                                                                                      • Review Submitted: 09-Jan-2010
                                                                                                      • Date of Stay: Dec 2009

                                                                                                      Fantastic Getaway

                                                                                                      5 of 5
                                                                                                      I can only echo what all of the other reviews have said. This is a wonderful cottage away from it all. It is kept in meticulous condition and you want for nothing. I debated writing a review as to keep this place a secret but decided it was o.k to share it! We spent time in there over Christmas so when we entered the house to the warm fireplace going, and the adorable Christmas tree we knew it was going to be magical. And it was. Can't wait to visit again. Thanks Bruce and Deanna!
                                                                                                      • Review Submitted: 05-Jan-2010
                                                                                                      • Date of Stay: Dec 2009