check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Sheffield: Vacation Rentals (48)

  • 1 - 48 of 48
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
        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
            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
                • 3 BR
                • 2 BA
                • Sleeps 4
                26
                  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
                                  • 2 BR
                                  • 2 BA
                                  • Sleeps 8
                                    • 3 BR
                                    • 1 BA
                                    • 1 HF BA
                                    • Sleeps 6
                                    1 Review
                                      • 3 BR
                                      • 2 BA
                                      • 1 HF BA
                                      • Sleeps 6
                                      1 Review
                                        • 4 BR
                                        • 3 BA
                                        • Sleeps 15
                                        11
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 8
                                            Excellent! 4.7/5
                                            (11 reviews)
                                            avg/night
                                            • 2 BR
                                            • 2 BA
                                            • Sleeps 6
                                            11
                                              • 4 BR
                                              • 3 BA
                                              • 1 HF BA
                                              • Sleeps 10
                                                • 5 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 11
                                                2 Reviews
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 2
                                                  1 Review
                                                    • 3 BR
                                                    • 3 BA
                                                    • Sleeps 12
                                                      • 4 BR
                                                      • 4 BA
                                                      • Sleeps 10
                                                      8
                                                        Exceptional! 5.0/5
                                                        (6 reviews)
                                                        avg/night
                                                        • 3 BR
                                                        • 2 BA
                                                        • 1 HF BA
                                                        • Sleeps 6
                                                        6
                                                          • 1 BR
                                                          • 1 BA
                                                          • Sleeps 2
                                                          4
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 6
                                                            1 Review
                                                              Wonderful! 4.9/5
                                                              (11 reviews)
                                                              avg/night
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 8
                                                              11
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 8
                                                                4
                                                                  • 4 BR
                                                                  • 2 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 10
                                                                  3
                                                                    • 4 BR
                                                                    • 1 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 8
                                                                    6
                                                                      Wonderful! 4.9/5
                                                                      (8 reviews)
                                                                      avg/night
                                                                      • 3 BR
                                                                      • 1 BA
                                                                      • Sleeps 6
                                                                      8
                                                                        • 5 BR
                                                                        • 3 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 16
                                                                        2 Reviews
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 6
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 8
                                                                            6
                                                                              • 3 BR
                                                                              • 1 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 8
                                                                              1 Review
                                                                                • 2 BR
                                                                                • 1 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 6
                                                                                1 Review
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  4
                                                                                    • 3 BR
                                                                                    • 1 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 6
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 10
                                                                                        • 4 BR
                                                                                        • 2 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 10
                                                                                        2 Reviews
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 4
                                                                                            • 3 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 6
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 8
                                                                                                Exceptional! 5.0/5
                                                                                                (5 reviews)
                                                                                                avg/night
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 10
                                                                                                5
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 6
                                                                                                  • 1 - 48 of 48
                                                                                                   

                                                                                                  Recent Sheffield Reviews

                                                                                                  Peaceful, private house near everything in the Berkshires

                                                                                                  4 of 5
                                                                                                  We spent a week in this very private home in a lovely, quiet neighborhood in Great Barrington. We enjoyed being a few minutes away from the "downtown" of Great Barrington and its shops and restaurants and also having the relaxing privacy of our rental. The house is also near Stockbridge (about 10-minutes) and Lenox is about a 15 - 20 minute drive. We especially loved the very large, attractive screen porch with its array of comfy furniture, dining table/chairs and the ceiling fan. It has sliders leading to the dining room/kitchen area. The house is well suited for two couples since it has two full bathrooms. The main floor has a nice two-sink plus tub/shower bathroom that has been newly remodeled and the downstairs (basement level with its large entertainment room) has another bathroom with a walk-in shower. There is also a laundry room in the basement area. Given that it was summer, we did not spend time in the basement entertainment area but I can imagine it would be a nice feature in the colder months with its big screen TV and pool table. The living room on the main floor is spacious and offers a large fireplace which would also be lovely on a cold day. There is a brand new deck but apparently because it is new, there is no deck furniture per se (although one could move furniture from the screen porch area). The deck is right off the porch room. We enjoyed our stay at this house and were also pleased with how Noriko dealt with a few concerns/glitches we encountered.
                                                                                                  • Submitted: Sep 13, 2016
                                                                                                  • Stayed: Aug 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