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Bennington: Houses, Condos & More (254)

  • 1 - 50 of 254
Additional fees apply. Taxes may be added.
    • 4 BR
    • 3 BA
    • 1 HF BA
    • Sleeps 8
    24
      • 6 BR
      • 4 BA
      • 1 HF BA
      • Sleeps 30
      10
        • 1 BR
        • 1 BA
        • Sleeps 4
        39
          • 3 BR
          • 1 BA
          • Sleeps 5
          13
            • 3 BR
            • 2 BA
            • 1 HF BA
            • Sleeps 7
            22
              • 3 BR
              • 3 BA
              • Sleeps 8
              10
                NEW!
                • 4 BR
                • 2 BA
                • Sleeps 8
                1 Review
                  • Studio
                  • 1 BA
                  • Sleeps 3
                    • 1 BR
                    • 1 BA
                    • Sleeps 6
                    48
                      NEW!
                      • Studio
                      • 1 BA
                      • Sleeps 1
                        • 4 BR
                        • 2 BA
                        • 1 HF BA
                        • Sleeps 8
                        2 Reviews
                          NEW!
                          • 4 BR
                          • 3 BA
                          • Sleeps 8
                          1 Review
                            • 2 BR
                            • 1 BA
                            • Sleeps 6
                            8
                              • 2 BR
                              • 2 BA
                              • Sleeps 6
                              5
                                • 4 BR
                                • 1 BA
                                • 1 HF BA
                                • Sleeps 8
                                3
                                  NEW!
                                  • 4 BR
                                  • 2 BA
                                  • Sleeps 12
                                    • 2 BR
                                    • 1 BA
                                    • Sleeps 8
                                    1 Review
                                      • 5 BR
                                      • 3 BA
                                      • 1 HF BA
                                      • Sleeps 14
                                      7
                                        NEW!
                                        • 2 BR
                                        • 2 BA
                                        • Sleeps 6
                                        2 Reviews
                                          • 2 BR
                                          • 1 BA
                                          • Sleeps 7
                                          10
                                            • 4 BR
                                            • 2 BA
                                            • Sleeps 8
                                            3
                                              • 4 BR
                                              • 2 BA
                                              • Sleeps 10
                                                NEW!
                                                • 3 BR
                                                • 1 BA
                                                • 1 HF BA
                                                • Sleeps 6
                                                  • 5 BR
                                                  • 5 BA
                                                  • Sleeps 12
                                                  1 Review
                                                    • 3 BR
                                                    • 2 BA
                                                    • Sleeps 5
                                                    26
                                                      • 3 BR
                                                      • 1 BA
                                                      • Sleeps 6
                                                      6
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        8
                                                          NEW!
                                                          • 5 BR
                                                          • 5 BA
                                                          • 1 HF BA
                                                          • Sleeps 10
                                                          2 Reviews
                                                            • 1 BR
                                                            • 1 BA
                                                            • Sleeps 4
                                                            24
                                                              • 2 BR
                                                              • 1 BA
                                                              • 1 HF BA
                                                              • Sleeps 6
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 4
                                                                11
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 6
                                                                  20
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    2 Reviews
                                                                      • 5 BR
                                                                      • 2 BA
                                                                      • 2 HF BA
                                                                      • Sleeps 11
                                                                      31
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • Sleeps 10
                                                                        12
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 6
                                                                          14
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 6
                                                                            2 Reviews
                                                                              • 5 BR
                                                                              • 4 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 10
                                                                              5
                                                                                • 3 BR
                                                                                • 1 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 2
                                                                                11
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  4
                                                                                    NEW!
                                                                                    • 3 BR
                                                                                    • 1 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 6
                                                                                    1 Review
                                                                                      NEW!
                                                                                      • 3 BR
                                                                                      • 1 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 5
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        7
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 8
                                                                                          5
                                                                                            • 3 BR
                                                                                            • 1 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 8
                                                                                            13
                                                                                              • 5 BR
                                                                                              • 2 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 14
                                                                                              17
                                                                                                • 4 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 13
                                                                                                39
                                                                                                  • 4 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 12
                                                                                                  3
                                                                                                    • 4 BR
                                                                                                    • 2 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 13
                                                                                                    7
                                                                                                      • 3 BR
                                                                                                      • 2 BA
                                                                                                      • Sleeps 8
                                                                                                      2 Reviews
                                                                                                      • 1 - 50 of 254
                                                                                                       

                                                                                                      Recent Bennington Reviews

                                                                                                      Peaceful Cottage Retreat is the perfect description for this rental

                                                                                                      5 of 5
                                                                                                      From the moment we got there, Brian and Samantha made us feel at home. They welcomed us and explained if we needed ANYTHING at all just come up to their house and they will oblige. Although we went to that area with a plan to do certain things and we really weren't on the property much during the day, but whenever we saw them it was evident they meant what they said. It WAS a wonderful place to come home to at the end of the day though. My wife and I were so comfortable there , it was like coming back to our actual home. Starting the day eating fresh eggs that they left in the fridge for us, and watching the hummingbirds out the kitchen window, and finishing the day sitting outside watching the millions of stars in the sky, it was a perfect vacation for both of us. The cleanliness of the property is such that I had no problem walking around the house barefoot ( and I am one step away from being Felix Unger............lol ). I would recommend this rental to anyone !!
                                                                                                      • Submitted: Aug 27, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      A unique home with modern and rustic influences.

                                                                                                      4 of 5
                                                                                                      We enjoyed our stay. The house is clean and comfortable. You can tell that the owners paid attention to detail in designing this home. The master suite library is a quiet space where I enjoyed reading some short stories. Having the pool and hot tub to ourselves was nice, and the kids enjoyed it. The cover to the hot tub was broke, which was a bit of a pain when getting in and out, but that was being replaced when we left. There's a country mouse(who loves butter apparently) so put ALL your food away at night. Lisa the caretaker is very nice and responsive when needed. It's a great location close to Williamstown, Ma and Bennington, Vermont. We hope to be back next year.
                                                                                                      • Submitted: Aug 18, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      Family Gathering in a Tranquil Setting

                                                                                                      5 of 5
                                                                                                      This property is an extremely spacious house with plenty of room for all family members. It offers great spaces for group gathering as well as secluded corners to hide away with a good book! Indoors and out the setting is beautiful and serene and you feel you are "away from it all." A highlight was a great kitchen and outdoor grill for cooking fabulous meals. An extra plus was the swimming pool and playground - fun for adults and children. Located in the heart of the country but just 15 minutes from the cute Bennington, VT downtown. A plus was multiple sleeping options for extended family, use of wifi, great games and dvd's for rainy days, tons of books to read and a very fun billiards table. The owner is extremely attentive and quickly responds to questions, makes suggestions for local activities and gives very detailed information about the layout of the home, bathroom locations, accessibility and other elements that make planning the stay easy. I would like to mention that the pool is even nicer and bigger than I thought from the pictures and the owner provides great pool toys, floats, goggles and such. I am not sure how deep the pool is but it was deep enough for a 16-year old to enjoy swimming and splashing but shallow enough for a 7-year old to be able to stand with head above water.
                                                                                                      • Submitted: Aug 12, 2016
                                                                                                      • Stayed: Jul 2016