check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr
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!

Chatham: House Rentals (173)

  • 1 - 50 of 173
Additional fees apply. Taxes may be added.
    • 3 BR
    • 2 BA
    • 1 HF BA
    • Sleeps 8
    2 Reviews
      • 6 BR
      • 5 BA
      • 1 HF BA
      • Sleeps 12
      1 Review
        NEW!
        • 3 BR
        • 3 BA
        • Sleeps 8
          • 3 BR
          • 2 BA
          • Sleeps 8
          1 Review
            • 2 BR
            • 2 BA
            • Sleeps 6
            6
              NEW!
              • 2 BR
              • 2 BA
              • Sleeps 6
              1 Review
                • 4 BR
                • 1 BA
                • 1 HF BA
                • Sleeps 8
                5
                  • 3 BR
                  • 2 BA
                  • 1 HF BA
                  • Sleeps 10
                  7
                    • 3 BR
                    • 2 BA
                    • 1 HF BA
                    • Sleeps 8
                      • 3 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 9
                        • 3 BR
                        • 3 BA
                        • Sleeps 6
                        5
                          NEW!
                          • 2 BR
                          • 1 BA
                          • Sleeps 4
                            NEW!
                            • 3 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 8
                            1 Review
                              • 3 BR
                              • 3 BA
                              • 2 HF BA
                              • Sleeps 11
                              3
                                • 4 BR
                                • 3 BA
                                • Sleeps 8
                                4
                                  • 4 BR
                                  • 3 BA
                                  • Sleeps 10
                                  2 Reviews
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 10
                                    5
                                      • 3 BR
                                      • 2 BA
                                      • Sleeps 11
                                      19
                                        NEW!
                                        • 2 BR
                                        • 1 BA
                                        • 1 HF BA
                                        • Sleeps 5
                                        1 Review
                                          NEW!
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 8
                                          5
                                            • 3 BR
                                            • 3 BA
                                            • Sleeps 8
                                            3
                                              • 3 BR
                                              • 3 BA
                                              • 1 HF BA
                                              • Sleeps 10
                                              6
                                                • 3 BR
                                                • 2 BA
                                                • 2 HF BA
                                                • Sleeps 8
                                                15
                                                  NEW!
                                                  • 6 BR
                                                  • 5 BA
                                                  • 1 HF BA
                                                  • Sleeps 10
                                                  4
                                                    • 4 BR
                                                    • 2 BA
                                                    • Sleeps 10
                                                    25
                                                      • 3 BR
                                                      • 3 BA
                                                      • Sleeps 9
                                                      4
                                                        • 5 BR
                                                        • 4 BA
                                                        • Sleeps 10
                                                        2 Reviews
                                                          • 4 BR
                                                          • 3 BA
                                                          • Sleeps 12
                                                          9
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 9
                                                            3
                                                              • 3 BR
                                                              • 1 BA
                                                              • Sleeps 7
                                                              8
                                                                • 6 BR
                                                                • 3 BA
                                                                • 1 HF BA
                                                                • Sleeps 16
                                                                2 Reviews
                                                                  • 3 BR
                                                                  • 2 BA
                                                                  • 1 HF BA
                                                                  • Sleeps 7
                                                                  6
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 8
                                                                    3
                                                                      • 2 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      17
                                                                        • 3 BR
                                                                        • 2 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 10
                                                                        8
                                                                          • 3 BR
                                                                          • 3 BA
                                                                          • Sleeps 8
                                                                          24
                                                                            • 3 BR
                                                                            • 3 BA
                                                                            • Sleeps 10
                                                                            10
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 7
                                                                              5
                                                                                • 3 BR
                                                                                • 3 BA
                                                                                • 1 HF BA
                                                                                • Sleeps 6
                                                                                5
                                                                                  • 3 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  8
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    3
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • 1 HF BA
                                                                                      • Sleeps 8
                                                                                      7
                                                                                        NEW!
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                          • 4 BR
                                                                                          • 3 BA
                                                                                          • Sleeps 6
                                                                                            NEW!
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 6
                                                                                                • 6 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 25
                                                                                                79
                                                                                                  • 3 BR
                                                                                                  • 2 BA
                                                                                                  • Sleeps 5
                                                                                                  13
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 10
                                                                                                    9
                                                                                                      • 3 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 5
                                                                                                      • 1 - 50 of 173
                                                                                                       

                                                                                                      Recent Chatham Reviews

                                                                                                      Amazing getaway!

                                                                                                      5 of 5
                                                                                                      We had a lovely time at Ed and Kathy's Grey House in Canaan, NY. It's really well-designed, and the furnishings were beautiful as well as comfortable. We particularly enjoyed the private feeling of the land--you can't see any other houses. The only thing to bear in mind is that you need to enable wifi calling on your phone, as there is no land line and almost no service. That said, you can text freely over wifi (and use your computer). Other than that, it was ideal, and a quick drive to Chatham, Williamstown and lots of local Berkshire fun.
                                                                                                      • Submitted: Aug 28, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      Perfect vacation home in berkshires

                                                                                                      5 of 5
                                                                                                      This was our first trip to Berkshire and this beautiful property made it a perfect home for our family. Our kids didn't want to leave the house at all. It's so peaceful and quite. The pool was a treat for the kids. The house has an open floor plan that makes for a good setup for kids and grown ups to spread out and still enjoy together. It is conveniently located to all Berkshire attractions. The owners are a text away and were quick to respond to our questions. We couldn't have found a better place for our week away in the berkshires.
                                                                                                      • Submitted: Aug 15, 2016
                                                                                                      • Stayed: Jul 2016

                                                                                                      Fun for All!

                                                                                                      5 of 5
                                                                                                      So much to do at the house. Plenty of space to spread out or be together. Big dining table in and out for family meals. We loved the game room of course with the pool table, karaoke, ping pong and all the rest. Jody had great communication with us all week as well as before and after our stay. Definitely enjoyed our week and the kids were so sad to leave!
                                                                                                      • Submitted: Aug 11, 2016
                                                                                                      • Stayed: Jul 2016