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Great Barrington: Houses, Cottages & More (576)

  • 1 - 50 of 576
Additional fees apply. Taxes may be added.
    • 6 BR
    • 4 BA
    • 1 HF BA
    • Sleeps 12
    17
      • 4 BR
      • 2 BA
      • Sleeps 8
      2 Reviews
        • 5 BR
        • 2 BA
        • Sleeps 10
        17
          • 4 BR
          • 3 BA
          • Sleeps 8
          7
            • 4 BR
            • 2 BA
            • 1 HF BA
            • Sleeps 8
            6
              • 5 BR
              • 3 BA
              • Sleeps 7
                • 2 BR
                • 1 BA
                • Sleeps 5
                43
                  • 2 BR
                  • 2 BA
                  • Sleeps 6
                  24
                    • 4 BR
                    • 2 BA
                    • 1 HF BA
                    • Sleeps 8
                      • 3 BR
                      • 2 BA
                      • Sleeps 6
                      15
                        • 3 BR
                        • 2 BA
                        • 1 HF BA
                        • Sleeps 6
                        6
                          • 2 BR
                          • 1 BA
                          • Sleeps 5
                          15
                            • 1 BR
                            • 1 BA
                            • Sleeps 4
                            16
                              • 3 BR
                              • 2 BA
                              • Sleeps 6
                              1 Review
                                • 3 BR
                                • 2 BA
                                • Sleeps 8
                                12
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 6
                                  22
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 8
                                    6
                                      • 4 BR
                                      • 3 BA
                                      • Sleeps 8
                                      1 Review
                                        • 5 BR
                                        • 3 BA
                                        • 1 HF BA
                                        • Sleeps 12
                                        25
                                          • 5 BR
                                          • 3 BA
                                          • Sleeps 10
                                          3
                                            • 3 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 6
                                            6
                                              • 4 BR
                                              • 3 BA
                                              • Sleeps 10
                                                • 4 BR
                                                • 3 BA
                                                • 1 HF BA
                                                • Sleeps 8
                                                1 Review
                                                  • 2 BR
                                                  • 1 BA
                                                  • Sleeps 10
                                                  15
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 2
                                                    10
                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 7
                                                      2 Reviews
                                                        • 5 BR
                                                        • 2 BA
                                                        • 1 HF BA
                                                        • Sleeps 10
                                                        9
                                                          • 4 BR
                                                          • 1 BA
                                                          • 1 HF BA
                                                          • Sleeps 8
                                                          9
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            6
                                                              • 3 BR
                                                              • 3 BA
                                                              • Sleeps 10
                                                              10
                                                                • 3 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                12
                                                                  • Studio
                                                                  • 1 BA
                                                                  • Sleeps 2
                                                                  1 Review
                                                                    • 5 BR
                                                                    • 2 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 12
                                                                    8
                                                                      • 3 BR
                                                                      • 3 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 10
                                                                      17
                                                                        • 4 BR
                                                                        • 2 BA
                                                                        • Sleeps 8
                                                                        25
                                                                          • 4 BR
                                                                          • 1 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 9
                                                                          9
                                                                            • 5 BR
                                                                            • 4 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 12
                                                                            7
                                                                              • 3 BR
                                                                              • 2 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 8
                                                                              19
                                                                                • 3 BR
                                                                                • 3 BA
                                                                                • Sleeps 9
                                                                                11
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 6
                                                                                    • 2 BR
                                                                                    • 1 BA
                                                                                    • Sleeps 4
                                                                                    9
                                                                                      • 3 BR
                                                                                      • 1 BA
                                                                                      • 2 HF BA
                                                                                      • Sleeps 7
                                                                                      15
                                                                                        • 5 BR
                                                                                        • 3 BA
                                                                                        • Sleeps 12
                                                                                        27
                                                                                          • 1 BR
                                                                                          • 1 BA
                                                                                          • Sleeps 4
                                                                                            • 2 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 5
                                                                                            20
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 8
                                                                                              4
                                                                                                • 4 BR
                                                                                                • 1 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 8
                                                                                                5
                                                                                                  • 3 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 6
                                                                                                  7
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 8
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                                                                                                    • 1 - 50 of 576
                                                                                                     

                                                                                                    Recent Great Barrington Reviews

                                                                                                    Eric's lake house was fantastic, above and beyond our expectations!

                                                                                                    5 of 5
                                                                                                    The lake house is a charming cottage in a private lakefront community. The back deck is actually on the water itself...getting up in the morning and walking right out to the lake made for a beautiful, relaxing vacation experience! The cottage itself is perfectly clean and very well appointed. It easily fit our family of 9. Eric left 2 kayaks for use to use and we spent literally hours out on the lake. We would gladly stay here again, probably longer next time now that we know how wonderful it is!
                                                                                                    • Submitted: Aug 30, 2016
                                                                                                    • Stayed: Aug 2016

                                                                                                    Alford Heaven with the STARS to prove it!

                                                                                                    5 of 5
                                                                                                    Sweet, comfortable, quiet, private, warm tasty breakfast pastries, wonderful walks, a wading brook, and great views. We chose to be away from the crowd for back to back concerts at Tanglewood, and chose the Smith Homestead from the pictures on the website. All was as pictured and described. Susan and Tom were congenial, helpful hosts for a wonderful anniversary get away weekend. The description was spot on, all was clean and welcoming with gorgeous Country Curtain linens and draperies. We had a fun lunch at the Brewery in Great Barrington, and did a couple of carry-in picnics to concerts the rest of the weekend. Susan's breakfasts hand-delivered in a big 'ol basket really were a special touch. The night sky from your doorway is beyond words. We will definitely share this with friends and family, and look forward to going back!
                                                                                                    • Submitted: Aug 28, 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