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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.

  • Showing 1-50 of 300+
Additional service fee may apply.
    Exceptional! 5.0/5
    (30 reviews)
    avg/night
    • 3 BR
    • 2 BA
    • Sleeps 4
    House #424508vb
    30
    Viewed 44 times in the last 48 hours
      Exceptional! 5.0/5
      (53 reviews)
      avg/night
      • 4 BR
      • 3 BA
      • Sleeps 9
      House #95599vb
      53
      Viewed 21 times in the last 48 hours
        Excellent! 4.6/5
        (15 reviews)
        avg/night
        • 2 BR
        • 1 BA
        • Sleeps 4
        Cottage #373357vb
        15
        Viewed 13 times in the last 48 hours
          Wonderful! 4.8/5
          (48 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 5
          Cabin #219964vb
          48
          Viewed 19 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 52 times in the last 48 hours
              Wonderful! 4.9/5
              (22 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • Separate Toilet
              • Sleeps 8
              House #332864vb
              22
              Viewed 12 times in the last 48 hours
                Exceptional! 5.0/5
                (19 reviews)
                avg/night
                • 3 BR
                • 3 BA
                • Sleeps 9
                Farmhouse #710105vb
                19
                Viewed 16 times in the last 48 hours
                  • 5 BR
                  • 2 BA
                  • Separate Toilet
                  • Sleeps 11
                  House #577344vb
                  3
                  Viewed 6 times in the last 48 hours
                    Wonderful! 4.9/5
                    (14 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • Separate Toilet
                    • Sleeps 6
                    Barn #179027
                    14
                    Viewed 27 times in the last 48 hours
                      Exceptional! 5.0/5
                      (7 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • Sleeps 6
                      House #384153
                      7
                        Wonderful! 4.9/5
                        (11 reviews)
                        avg/night
                        • 4 BR
                        • 3 BA
                        • Sleeps 15
                        House #512619vb
                        11
                        Viewed 47 times in the last 48 hours
                          avg/night
                          • 2 BR
                          • 2 BA
                          • Sleeps 4
                          House #719709vb
                          3
                          Viewed 10 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 9 times in the last 48 hours
                                • 3 BR
                                • 2 BA
                                • Separate Toilet
                                • Sleeps 6
                                House #3558842
                                1
                                  avg/night
                                  • 3 BR
                                  • 2 BA
                                  • Separate Toilet
                                  • Sleeps 6
                                  House #4317148
                                  1
                                  Viewed 5 times in the last 48 hours
                                    Exceptional! 5.0/5
                                    (5 reviews)
                                    avg/night
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 8
                                    Chateau / Country House #4021614
                                    5
                                    Viewed 8 times in the last 48 hours
                                      avg/night
                                      • 4 BR
                                      • 3 BA
                                      • Separate Toilet
                                      • Sleeps 10
                                      House #772872vb
                                      0
                                      Viewed 20 times in the last 48 hours
                                        • 2 BR
                                        • 2 BA
                                        • Separate Toilet
                                        • Sleeps 8
                                        House #104868
                                        4
                                          • 3 BR
                                          • 2 BA
                                          • Separate Toilet
                                          • Sleeps 8
                                          House #497959vb
                                          4
                                          Viewed 14 times in the last 48 hours
                                            • 3 BR
                                            • 3 BA
                                            • Sleeps 10
                                            House #575213vb
                                            0
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 6
                                              House #953681vb
                                              0
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 8
                                                House #124299
                                                0
                                                Viewed 9 times in the last 48 hours
                                                  Exceptional! 5.0/5
                                                  (21 reviews)
                                                  avg/night
                                                  • 4 BR
                                                  • 3 BA
                                                  • Separate Toilet
                                                  • Sleeps 8
                                                  Chateau / Country House #396464vb
                                                  21
                                                  Viewed 30 times in the last 48 hours
                                                    Exceptional! 5.0/5
                                                    (8 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 4 BA
                                                    • Sleeps 10
                                                    House #453690vb
                                                    8
                                                    Viewed 14 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (6 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      House #804956vb
                                                      6
                                                      Viewed 32 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (15 reviews)
                                                        avg/night
                                                        • 6 BR
                                                        • 5 BA
                                                        • Sleeps 20
                                                        Estate #4258796
                                                        15
                                                        Viewed 195 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (9 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 7
                                                          House #330190
                                                          9
                                                          Viewed 9 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (20 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 5
                                                            Cottage #707780vb
                                                            20
                                                            Viewed 35 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (32 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              House #406592vb
                                                              32
                                                              Viewed 31 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (9 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                Cottage #3790476
                                                                9
                                                                Viewed 9 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (7 reviews)
                                                                  avg/night
                                                                  • 5 BR
                                                                  • 4 BA
                                                                  • Separate Toilet
                                                                  • Sleeps 12
                                                                  Chateau / Country House #777079vb
                                                                  7
                                                                  Viewed 23 times in the last 48 hours
                                                                    Excellent! 4.6/5
                                                                    (49 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    Cabin #182224
                                                                    49
                                                                    Viewed 53 times in the last 48 hours
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      House #711169vb
                                                                      3
                                                                      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 23 times in the last 48 hours
                                                                          Wonderful! 4.8/5
                                                                          (38 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          Cottage #293009
                                                                          38
                                                                          Viewed 91 times in the last 48 hours
                                                                            Excellent! 4.7/5
                                                                            (7 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            Farmhouse #3765427
                                                                            7
                                                                            Viewed 15 times in the last 48 hours
                                                                              Wonderful! 4.8/5
                                                                              (18 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 3 BA
                                                                              • Separate Toilet
                                                                              • Sleeps 10
                                                                              House #272149vb
                                                                              18
                                                                              Viewed 23 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 32 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 13 times in the last 48 hours
                                                                                    Excellent! 4.7/5
                                                                                    (25 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 1 BA
                                                                                    • Separate Toilet
                                                                                    • Sleeps 6
                                                                                    House #178378
                                                                                    25
                                                                                    Viewed 66 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (10 reviews)
                                                                                      avg/night
                                                                                      • 6 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 10
                                                                                      House #4064007
                                                                                      10
                                                                                      Viewed 33 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (13 reviews)
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 3
                                                                                        Cottage #555172vb
                                                                                        13
                                                                                        Viewed 12 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (17 reviews)
                                                                                          avg/night
                                                                                          • 5 BR
                                                                                          • 2 BA
                                                                                          • Separate Toilet
                                                                                          • Sleeps 12
                                                                                          House #561543vb
                                                                                          17
                                                                                          Viewed 8 times in the last 48 hours
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 3
                                                                                            Cabin #4153303
                                                                                            3
                                                                                            Viewed 14 times in the last 48 hours
                                                                                              Wonderful! 4.8/5
                                                                                              (9 reviews)
                                                                                              avg/night
                                                                                              • 2 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 5
                                                                                              Farmhouse #719766vb
                                                                                              9
                                                                                              Viewed 19 times in the last 48 hours
                                                                                                Exceptional! 5.0/5
                                                                                                (16 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Separate Toilet
                                                                                                • Sleeps 12
                                                                                                House #583082vb
                                                                                                16
                                                                                                Viewed 43 times in the last 48 hours
                                                                                                  avg/night
                                                                                                  • 4 BR
                                                                                                  • 2 BA
                                                                                                  • Separate Toilet
                                                                                                  • Sleeps 8
                                                                                                  House #4222851
                                                                                                  0
                                                                                                  Viewed 5 times in the last 48 hours
                                                                                                    Wonderful! 4.8/5
                                                                                                    (25 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 1 BA
                                                                                                    • Sleeps 6
                                                                                                    House #3002193
                                                                                                    25
                                                                                                    Viewed 33 times in the last 48 hours
                                                                                                      Wonderful! 4.9/5
                                                                                                      (16 reviews)
                                                                                                      avg/night
                                                                                                      • 6 BR
                                                                                                      • 5 BA
                                                                                                      • Sleeps 12
                                                                                                      House #406384vb
                                                                                                      16
                                                                                                      Viewed 62 times in the last 48 hours
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