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Sheffield: Houses, Cottages & More (137)

  • 1 - 50 of 137
Additional fees apply. Taxes may be added.
    Exceptional! 5.0/5
    (49 reviews)
    avg/night
    • 4 BR
    • 3 BA
    • Sleeps 9
    49
      • 4 BR
      • 3 BA
      • 1 HF BA
      • Sleeps 10
        Exceptional! 5.0/5
        (20 reviews)
        View details for price
        • 4 BR
        • 3 BA
        • 1 HF BA
        • Sleeps 8
        20
          Wonderful! 4.8/5
          (44 reviews)
          avg/night
          • 2 BR
          • 1 BA
          • Sleeps 5
          44
            • 5 BR
            • 3 BA
            • 1 HF BA
            • Sleeps 16
            3
              • 3 BR
              • 2 BA
              • Sleeps 4
              26
                Wonderful! 4.9/5
                (18 reviews)
                avg/night
                • 3 BR
                • 2 BA
                • Sleeps 8
                18
                  • 2 BR
                  • 2 BA
                  • 1 HF BA
                  • Sleeps 8
                  4
                    Wonderful! 4.8/5
                    (19 reviews)
                    avg/night
                    • 3 BR
                    • 2 BA
                    • 1 HF BA
                    • Sleeps 8
                    19
                      Exceptional! 5.0/5
                      (17 reviews)
                      avg/night
                      • 3 BR
                      • 3 BA
                      • Sleeps 9
                      17
                        Excellent! 4.6/5
                        (14 reviews)
                        avg/night
                        • 2 BR
                        • 1 BA
                        • Sleeps 4
                        14
                          Exceptional! 5.0/5
                          (5 reviews)
                          avg/night
                          • 4 BR
                          • 2 BA
                          • Sleeps 8
                          5
                            • 4 BR
                            • 3 BA
                            • 1 HF BA
                            • Sleeps 10
                            2 Reviews
                              • 3 BR
                              • 2 BA
                              • 1 HF BA
                              • Sleeps 8
                              4
                                Exceptional! 5.0/5
                                (7 reviews)
                                avg/night
                                • 3 BR
                                • 2 BA
                                • Sleeps 6
                                7
                                  • 5 BR
                                  • 1 HF BA
                                  • Sleeps 14
                                  2 Reviews
                                    • 3 BR
                                    • 1 BA
                                    • 1 HF BA
                                    • Sleeps 6
                                    1 Review
                                      • 2 BR
                                      • 2 BA
                                      • Sleeps 8
                                        • 3 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 6
                                        1 Review
                                          • 4 BR
                                          • 3 BA
                                          • Sleeps 15
                                          11
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 8
                                              • 4 BR
                                              • 3 BA
                                              • 1 HF BA
                                              • Sleeps 10
                                                • 5 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 11
                                                2 Reviews
                                                  • 3 BR
                                                  • 3 BA
                                                  • Sleeps 10
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 2
                                                    1 Review
                                                      • 4 BR
                                                      • 4 BA
                                                      • Sleeps 10
                                                      8
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        1 Review
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 2
                                                          4
                                                            • 5 BR
                                                            • 3 BA
                                                            • 1 HF BA
                                                            • Sleeps 16
                                                            2 Reviews
                                                              Wonderful! 4.9/5
                                                              (11 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              11
                                                                • 3 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                  Wonderful! 4.8/5
                                                                  (27 reviews)
                                                                  avg/night
                                                                  • 5 BR
                                                                  • 3 BA
                                                                  • Sleeps 12
                                                                  27
                                                                    • 2 BR
                                                                    • 2 BA
                                                                    • Sleeps 4
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 10
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 10
                                                                        3
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                            Wonderful! 4.9/5
                                                                            (16 reviews)
                                                                            avg/night
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 5
                                                                            16
                                                                              • 3 BR
                                                                              • 1 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 8
                                                                              1 Review
                                                                                Excellent! 4.7/5
                                                                                (22 reviews)
                                                                                avg/night
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • Sleeps 5
                                                                                22
                                                                                  Exceptional! 5.0/5
                                                                                  (6 reviews)
                                                                                  avg/night
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 6
                                                                                  6
                                                                                    • 4 BR
                                                                                    • 1 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 8
                                                                                    6
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 10
                                                                                      2 Reviews
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 8
                                                                                        6
                                                                                          • 3 BR
                                                                                          • 1 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 6
                                                                                            Exceptional! 5.0/5
                                                                                            (5 reviews)
                                                                                            avg/night
                                                                                            • 4 BR
                                                                                            • 3 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 10
                                                                                            5
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 8
                                                                                              4
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 6
                                                                                                1 Review
                                                                                                  Wonderful! 4.9/5
                                                                                                  (8 reviews)
                                                                                                  avg/night
                                                                                                  • 3 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 6
                                                                                                  8
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    1 Review
                                                                                                    • 1 - 50 of 137
                                                                                                     

                                                                                                    Recent Sheffield Reviews

                                                                                                    Perfect getaway

                                                                                                    5 of 5
                                                                                                    This is our 3rd time returning to the schoolhouse cottage and we plan to continue the yearly tradition. The cottage is clean, spacious and feels like a home away from home. Nestled up against wooded property it is quiet and peaceful yet a few minutes drive to the center of town. Excellent restaurants, shopping and hiking nearby. Our host is more than welcoming every year and we look forward to our return trip.
                                                                                                    • Submitted: Sep 19, 2016
                                                                                                    • Stayed: Sep 2016

                                                                                                    lovely week in the Berkshires

                                                                                                    5 of 5
                                                                                                    The house was perfect for a week in August in the Berkshires. Comfortable, great front porch, big back yard, and ideally located near a lake for swimming and a short walk to downtown GB.
                                                                                                    • Submitted: Sep 8, 2016
                                                                                                    • Stayed: Aug 2016

                                                                                                    Great house, very close to town, fantastic stay!

                                                                                                    5 of 5
                                                                                                    My wife and two young kids stayed in Trish's house for a week in August. The house is fantastic as it is basically all new and very comfortable, and big too. The kitchen is great and we were able to cook a lot, and the porch has great views. Beds are comfy and there is really a ton of room to spread out, which is great for us (a family living in an apartment in NYC). Also, the house is so close to downtown Great Barrington, it is just down the hill and over the train tracks. And Great Barrington is very centrally located in the Berkshires. Finally, Trish was the nicest owner I've ever dealt with on VRBO, she is great and will endeavor to make your stay the best. Five stars!
                                                                                                    • Submitted: Aug 23, 2016
                                                                                                    • Stayed: Aug 2016