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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    Exceptional! 5.0/5
    (53 reviews)
    avg/night
    • 4 BR
    • 3 BA
    • Sleeps 9
    House #95599vb
    53
    Viewed 22 times in the last 48 hours
      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
        (21 reviews)
        avg/night
        • 4 BR
        • 3 BA
        • 1 HF BA
        • Sleeps 8
        Chateau / Country House #396464vb
        21
        Viewed 11 times in the last 48 hours
          Wonderful! 4.8/5
          (48 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 5
          Cabin #219964vb
          48
          Viewed 23 times in the last 48 hours
            Excellent! 4.6/5
            (15 reviews)
            avg/night
            • 2 BR
            • 1 BA
            • Sleeps 4
            Cottage #373357vb
            15
            Viewed 14 times in the last 48 hours
              Wonderful! 4.9/5
              (22 reviews)
              avg/night
              • 3 BR
              • 2 BA
              • 1 HF BA
              • Sleeps 8
              House #332864vb
              22
              Viewed 12 times in the last 48 hours
                Exceptional! 5.0/5
                (6 reviews)
                avg/night
                • 5 BR
                • 3 BA
                • 1 HF BA
                • Sleeps 16
                House #866131vb
                6
                Viewed 49 times in the last 48 hours
                  avg/night
                  • 2 BR
                  • 2 BA
                  • 1 HF BA
                  • Sleeps 8
                  House #104868
                  4
                  Viewed 5 times in the last 48 hours
                    Exceptional! 5.0/5
                    (19 reviews)
                    avg/night
                    • 3 BR
                    • 3 BA
                    • Sleeps 9
                    Farmhouse #710105vb
                    19
                    Viewed 15 times in the last 48 hours
                      • 5 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 11
                      House #577344vb
                      3
                      Viewed 11 times in the last 48 hours
                        Wonderful! 4.9/5
                        (14 reviews)
                        avg/night
                        • 3 BR
                        • 2 BA
                        • 1 HF BA
                        • Sleeps 6
                        Barn #179027
                        14
                        Viewed 41 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 49 times in the last 48 hours
                              avg/night
                              • 2 BR
                              • 2 BA
                              • Sleeps 4
                              House #719709vb
                              3
                              Viewed 7 times in the last 48 hours
                                • 1 BR
                                • 1 BA
                                • Sleeps 2
                                Apartment #766104vb
                                2
                                  avg/night
                                  • 3 BR
                                  • 1 BA
                                  • 1 HF BA
                                  • Sleeps 6
                                  House #3893807
                                  1
                                  Viewed 26 times in the last 48 hours
                                    avg/night
                                    • 3 BR
                                    • 2 BA
                                    • 1 HF BA
                                    • Sleeps 6
                                    House #3558842
                                    1
                                    Viewed 5 times in the last 48 hours
                                      • 3 BR
                                      • 2 BA
                                      • 1 HF BA
                                      • Sleeps 6
                                      House #4317148
                                      1
                                        Exceptional! 5.0/5
                                        (5 reviews)
                                        avg/night
                                        • 4 BR
                                        • 2 BA
                                        • Sleeps 8
                                        Chateau / Country House #4021614
                                        5
                                          avg/night
                                          • 4 BR
                                          • 3 BA
                                          • 1 HF BA
                                          • Sleeps 10
                                          House #772872vb
                                          0
                                          Viewed 20 times in the last 48 hours
                                            • 3 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 8
                                            House #497959vb
                                            4
                                            Viewed 5 times in the last 48 hours
                                              avg/night
                                              • 3 BR
                                              • 3 BA
                                              • Sleeps 10
                                              House #575213vb
                                              0
                                              Viewed 6 times in the last 48 hours
                                                • 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
                                                    (8 reviews)
                                                    avg/night
                                                    • 4 BR
                                                    • 4 BA
                                                    • Sleeps 10
                                                    House #453690vb
                                                    8
                                                    Viewed 8 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (6 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 6
                                                      House #804956vb
                                                      6
                                                      Viewed 16 times in the last 48 hours
                                                        Exceptional! 5.0/5
                                                        (14 reviews)
                                                        avg/night
                                                        • 6 BR
                                                        • 5 BA
                                                        • Sleeps 20
                                                        Estate #4258796
                                                        14
                                                        Viewed 174 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (9 reviews)
                                                          avg/night
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 7
                                                          House #330190
                                                          9
                                                          Viewed 13 times in the last 48 hours
                                                            Wonderful! 4.9/5
                                                            (20 reviews)
                                                            avg/night
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 5
                                                            Cottage #707780vb
                                                            20
                                                            Viewed 30 times in the last 48 hours
                                                              Wonderful! 4.9/5
                                                              (32 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              House #406592vb
                                                              32
                                                              Viewed 30 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (9 reviews)
                                                                avg/night
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 6
                                                                Cottage #3790476
                                                                9
                                                                Viewed 13 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (7 reviews)
                                                                  avg/night
                                                                  • 5 BR
                                                                  • 4 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 12
                                                                  Chateau / Country House #777079vb
                                                                  7
                                                                  Viewed 15 times in the last 48 hours
                                                                    Excellent! 4.6/5
                                                                    (49 reviews)
                                                                    avg/night
                                                                    • 2 BR
                                                                    • 1 BA
                                                                    • Sleeps 4
                                                                    Cabin #182224
                                                                    49
                                                                    Viewed 38 times in the last 48 hours
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      House #711169vb
                                                                      3
                                                                      Viewed 38 times in the last 48 hours
                                                                        Wonderful! 4.9/5
                                                                        (23 reviews)
                                                                        avg/night
                                                                        • 5 BR
                                                                        • 5 BA
                                                                        • Sleeps 12
                                                                        House #729783vb
                                                                        23
                                                                        Viewed 27 times in the last 48 hours
                                                                          Wonderful! 4.8/5
                                                                          (38 reviews)
                                                                          avg/night
                                                                          • 2 BR
                                                                          • 2 BA
                                                                          • Sleeps 6
                                                                          Cottage #293009
                                                                          38
                                                                          Viewed 72 times in the last 48 hours
                                                                            Excellent! 4.7/5
                                                                            (7 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            Farmhouse #3765427
                                                                            7
                                                                            Viewed 8 times in the last 48 hours
                                                                              Wonderful! 4.8/5
                                                                              (18 reviews)
                                                                              avg/night
                                                                              • 3 BR
                                                                              • 3 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 10
                                                                              House #272149vb
                                                                              18
                                                                              Viewed 36 times in the last 48 hours
                                                                                Exceptional! 5.0/5
                                                                                (17 reviews)
                                                                                avg/night
                                                                                • 6 BR
                                                                                • 4 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 12
                                                                                Estate #629154vb
                                                                                17
                                                                                Viewed 9 times in the last 48 hours
                                                                                  Exceptional! 5.0/5
                                                                                  (14 reviews)
                                                                                  avg/night
                                                                                  • 5 BR
                                                                                  • 2 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 10
                                                                                  Barn #616214vb
                                                                                  14
                                                                                  Viewed 20 times in the last 48 hours
                                                                                    Excellent! 4.7/5
                                                                                    (25 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 1 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 6
                                                                                    House #178378
                                                                                    25
                                                                                    Viewed 57 times in the last 48 hours
                                                                                      Exceptional! 5.0/5
                                                                                      (10 reviews)
                                                                                      avg/night
                                                                                      • 6 BR
                                                                                      • 3 BA
                                                                                      • Sleeps 10
                                                                                      House #4064007
                                                                                      10
                                                                                      Viewed 35 times in the last 48 hours
                                                                                        Wonderful! 4.9/5
                                                                                        (13 reviews)
                                                                                        $89
                                                                                        avg/night
                                                                                        • 1 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 3
                                                                                        Cottage #555172vb
                                                                                        13
                                                                                        Viewed 13 times in the last 48 hours
                                                                                          Wonderful! 4.9/5
                                                                                          (17 reviews)
                                                                                          avg/night
                                                                                          • 5 BR
                                                                                          • 2 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 12
                                                                                          House #561543vb
                                                                                          17
                                                                                          Viewed 14 times in the last 48 hours
                                                                                            • 1 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 3
                                                                                            Cabin #4153303
                                                                                            3
                                                                                            Viewed 15 times in the last 48 hours
                                                                                              Exceptional! 5.0/5
                                                                                              (16 reviews)
                                                                                              avg/night
                                                                                              • 4 BR
                                                                                              • 3 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 12
                                                                                              House #583082vb
                                                                                              16
                                                                                              Viewed 41 times in the last 48 hours
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 2 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 8
                                                                                                House #4222851
                                                                                                0
                                                                                                Viewed 6 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (25 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 6
                                                                                                  House #3002193
                                                                                                  25
                                                                                                  Viewed 34 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (16 reviews)
                                                                                                    avg/night
                                                                                                    • 6 BR
                                                                                                    • 5 BA
                                                                                                    • Sleeps 12
                                                                                                    House #406384vb
                                                                                                    16
                                                                                                    Viewed 96 times in the last 48 hours
                                                                                                      Wonderful! 4.8/5
                                                                                                      (9 reviews)
                                                                                                      avg/night
                                                                                                      • 2 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 5
                                                                                                      Farmhouse #719766vb
                                                                                                      9
                                                                                                      Viewed 15 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Sheffield: Houses, Cottages & More (300+)

                                                                                                       

                                                                                                      Recent Sheffield Reviews

                                                                                                      Amazing house for large group

                                                                                                      5 of 5
                                                                                                      Stayed here for a four day weekend to celebrate New Years with a group of ten of us. The house was perfect could not ask for a more accommodating place to get away from the city and relax with friends. There was more than enough room where ten adults felt spread out and there where extra beds and a futon still empty. The layout of the house is ideal all the bedrooms are upstairs with an extra tv space. The down stairs is a large open space with living room, dining room, and the kitchen. We had a chef come and cook for us for NYE and it was great being able to spread out in one room. Went skiing a few days at Jiminy Peak which is less than an hour drive. Every one already can't wait to return in the summer.
                                                                                                      • Submitted: Jan 5, 2017
                                                                                                      • Stayed: Dec 2016

                                                                                                      Perfectly Fantastic Family Weekend

                                                                                                      5 of 5
                                                                                                      The Playhouse provides all that is necessary to have a fabulous time with family or a large group. I have looked for a place to hold our annual family Christmas gathering for quite some time and came across the listing for The Playhouse. Our annual holiday trip with our two grown children and their families to visit my husband's hometown and family in the Berkshires involved getting five hotel rooms and not enough room to enjoy everyone's company. The Playhouse fills this need in a wonderful way. The open areas are spacious and easily accommodated our large gathering on Saturday afternoon with brothers, sisters, nieces and nephews from 14 weeks to 70 years. On the main floor, the great room with it's open beams, beautiful lighting, wonderful views and great sound system was perfect setting for the adults at our gathering. Downstairs, the playroom area was great for the younger children to play ping pong and board games. Never once did we hear "I'm bored". The two kitchens are well equipped to handle cooking and serving food for our large group. The bedrooms are set up for convenience, comfort and a quiet retreat from activity. The mattresses and bedding are the best! Bathrooms plentiful and the heated floors much appreciated with 11 degree weather outside. The night we arrived we had eight inches of snow and the property manager Sean was there to dig us out first thing in the morning. He was informative upon our arrival and very responsive if we called him with a question. The property owner Daniel was also very accommodating and responsive. Much thought went into the planning and design of The Playhouse for beauty, comfort and function. Finally, my best recommendation is that we have already booked The Playhouse again for even longer stay next year.
                                                                                                      • Submitted: Dec 21, 2016
                                                                                                      • Stayed: Dec 2016

                                                                                                      Lovely!

                                                                                                      5 of 5
                                                                                                      What a warm and charming cottage! The location is extremely convenient. Ruth and Gareth were very welcoming. We will stay agian.
                                                                                                      • Submitted: Dec 1, 2016
                                                                                                      • Stayed: Nov 2016