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  • Showing 1-50 of 300+
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    Exceptional! 5.0/5
    (53 reviews)
    avg/night
    • 4 BR
    • 3 BA
    • Sleeps 9
    House #95599vb
    53
    Viewed 27 times in the last 48 hours
      Wonderful! 4.8/5
      (48 reviews)
      avg/night
      • 2 BR
      • 1 BA
      • Sleeps 5
      Cabin #219964vb
      48
      Viewed 24 times in the last 48 hours
        Exceptional! 5.0/5
        (30 reviews)
        avg/night
        • 3 BR
        • 2 BA
        • Sleeps 4
        House #424508vb
        30
        Viewed 62 times in the last 48 hours
          Excellent! 4.6/5
          (15 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 4
          Cottage #373357vb
          15
            Exceptional! 5.0/5
            (6 reviews)
            avg/night
            • 5 BR
            • 3 BA
            • 1 HF BA
            • Sleeps 16
            House #866131vb
            6
            Viewed 76 times in the last 48 hours
              Exceptional! 5.0/5
              (20 reviews)
              avg/night
              • 3 BR
              • 3 BA
              • Sleeps 9
              Farmhouse #710105vb
              20
              Viewed 10 times in the last 48 hours
                avg/night
                • 2 BR
                • 2 BA
                • 1 HF BA
                • Sleeps 8
                House #104868
                4
                Viewed 9 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 13 times in the last 48 hours
                    • 5 BR
                    • 2 BA
                    • 1 HF BA
                    • Sleeps 11
                    House #577344vb
                    3
                      Wonderful! 4.9/5
                      (14 reviews)
                      avg/night
                      • 3 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 6
                      Barn #179027
                      14
                      Viewed 18 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 25 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
                                • 1 HF BA
                                • Sleeps 6
                                House #3893807
                                2
                                Viewed 5 times in the last 48 hours
                                  • 3 BR
                                  • 2 BA
                                  • 1 HF BA
                                  • Sleeps 6
                                  House #3558842
                                  1
                                    • 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
                                        Viewed 6 times in the last 48 hours
                                          • 3 BR
                                          • 2 BA
                                          • 1 HF BA
                                          • Sleeps 8
                                          House #497959vb
                                          4
                                          Viewed 10 times in the last 48 hours
                                            • 3 BR
                                            • 3 BA
                                            • Sleeps 10
                                            House #575213vb
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 6
                                              House #953681vb
                                                avg/night
                                                • 2 BR
                                                • 2 BA
                                                • Sleeps 8
                                                House #124299
                                                Viewed 16 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 33 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (15 reviews)
                                                      avg/night
                                                      • 6 BR
                                                      • 5 BA
                                                      • Sleeps 20
                                                      Estate #4258796
                                                      15
                                                      Viewed 188 times in the last 48 hours
                                                        Wonderful! 4.9/5
                                                        (9 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 7
                                                        House #330190
                                                        9
                                                        Viewed 7 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (20 reviews)
                                                          avg/night
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 5
                                                          Cottage #707780vb
                                                          20
                                                          Viewed 56 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
                                                              Wonderful! 4.9/5
                                                              (32 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              House #406592vb
                                                              32
                                                              Viewed 19 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
                                                                  Exceptional! 5.0/5
                                                                  (7 reviews)
                                                                  avg/night
                                                                  • 5 BR
                                                                  • 4 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 12
                                                                  Chateau / Country House #777079vb
                                                                  7
                                                                  Viewed 29 times in the last 48 hours
                                                                    • 4 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    House #711169vb
                                                                    3
                                                                    Viewed 33 times in the last 48 hours
                                                                      Wonderful! 4.9/5
                                                                      (23 reviews)
                                                                      avg/night
                                                                      • 5 BR
                                                                      • 5 BA
                                                                      • Sleeps 12
                                                                      House #729783vb
                                                                      23
                                                                      Viewed 39 times in the last 48 hours
                                                                        Wonderful! 4.8/5
                                                                        (38 reviews)
                                                                        avg/night
                                                                        • 2 BR
                                                                        • 2 BA
                                                                        • Sleeps 6
                                                                        Cottage #293009
                                                                        38
                                                                        Viewed 49 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 20 times in the last 48 hours
                                                                            Excellent! 4.7/5
                                                                            (7 reviews)
                                                                            avg/night
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            Farmhouse #3765427
                                                                            7
                                                                            Viewed 12 times in the last 48 hours
                                                                              Exceptional! 5.0/5
                                                                              (10 reviews)
                                                                              avg/night
                                                                              • 6 BR
                                                                              • 3 BA
                                                                              • Sleeps 10
                                                                              House #4064007
                                                                              10
                                                                              Viewed 58 times in the last 48 hours
                                                                                Wonderful! 4.8/5
                                                                                (11 reviews)
                                                                                avg/night
                                                                                • 1 BR
                                                                                • 1 BA
                                                                                • Sleeps 4
                                                                                Apartment #437137vb
                                                                                11
                                                                                Viewed 40 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 38 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 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 16 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 16 times in the last 48 hours
                                                                                          Excellent! 4.7/5
                                                                                          (7 reviews)
                                                                                          avg/night
                                                                                          • 4 BR
                                                                                          • 1 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 8
                                                                                          House #700566vb
                                                                                          7
                                                                                          Viewed 12 times in the last 48 hours
                                                                                            Wonderful! 4.9/5
                                                                                            (16 reviews)
                                                                                            avg/night
                                                                                            • 6 BR
                                                                                            • 6 BA
                                                                                            • Sleeps 12
                                                                                            Estate #568397vb
                                                                                            16
                                                                                            Viewed 24 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 7 times in the last 48 hours
                                                                                                • 1 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 3
                                                                                                Cabin #4153303
                                                                                                3
                                                                                                Viewed 26 times in the last 48 hours
                                                                                                  Wonderful! 4.8/5
                                                                                                  (9 reviews)
                                                                                                  avg/night
                                                                                                  • 2 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 5
                                                                                                  Farmhouse #719766vb
                                                                                                  9
                                                                                                  Viewed 13 times in the last 48 hours
                                                                                                    Wonderful! 4.9/5
                                                                                                    (16 reviews)
                                                                                                    avg/night
                                                                                                    • 6 BR
                                                                                                    • 5 BA
                                                                                                    • Sleeps 12
                                                                                                    House #406384vb
                                                                                                    16
                                                                                                    Viewed 73 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 40 times in the last 48 hours
                                                                                                      • 1 - 50 of 300+

                                                                                                      Sheffield: Vacation Rentals (467)

                                                                                                       

                                                                                                      Recent Sheffield Reviews

                                                                                                      Cozy winter visit

                                                                                                      5 of 5
                                                                                                      We had a really nice stay over New Years weekend. The house was comfortable and cozy, with lots of toys and games for our granddaughter--who also loved visiting the goats. We're sorry that it was winter, because the pool and patio area looked great!
                                                                                                      • Submitted: Jan 24, 2017
                                                                                                      • Stayed: Dec 2016

                                                                                                      Stunning- perfect group getaway!

                                                                                                      5 of 5
                                                                                                      Me & my husband came here for our weekend wedding celebration with our family & friends. This house has EVERYTHING you need to enjoy yourself. We had enough space for 20 people (including kids and even our pup!) to sleep and play with more than enough room. It goes without saying that the architecture is stunning (It looks even better in person than the photos!) The property manager was attentive to our needs if anything came up, without intruding on our privacy. They even left out a dog bed & water bowl for our pup! The downstairs was a great playroom with the tv and table tennis. They had already set up the airbeds for us for the extra guests sleeping in the yoga studio! It was the perfect weekend that we'll remember for ever! Just a couple things to note: the hot tub was at the house but elsewhere on the property (it might say this in the listing, so maybe we just didn't read correctly) and the fireplace is downstairs (and currently not working, which would have been nice to have a heads up on.) otherwise, this house far surpassed our expectations. The property its on is quiet & serene.
                                                                                                      • Submitted: Jan 20, 2017
                                                                                                      • Stayed: Jan 2017

                                                                                                      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