check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr
Use filters to narrow your search results!

Chesterfield: Houses, Apartments & More (120)

  • 1 - 50 of 120
Additional fees apply. Taxes may be added.
    • 1 BR
    • 1 BA
    • Sleeps 4
    15
      • 2 BR
      • 1 BA
      • Sleeps 4
      13
        • 4 BR
        • 2 BA
        • 1 HF BA
        • Sleeps 8
        3
          • 2 BR
          • 1 BA
          • Sleeps 6
          12
            • 2 BR
            • 2 BA
            • Sleeps 6
            22
              • 4 BR
              • 3 BA
              • Sleeps 10
              14
                • 2 BR
                • 1 BA
                • Sleeps 6
                15
                  • 2 BR
                  • 1 BA
                  • Sleeps 8
                  22
                    • 4 BR
                    • 4 BA
                    • Sleeps 6
                    7
                      • 3 BR
                      • 1 BA
                      • 1 HF BA
                      • Sleeps 6
                      1 Review
                        • 4 BR
                        • 2 BA
                        • Sleeps 8
                        10
                          • 2 BR
                          • 1 BA
                          • Sleeps 5
                          15
                            • 1 BR
                            • 1 BA
                            • Sleeps 3
                              • 4 BR
                              • 2 BA
                              • Sleeps 8
                              2 Reviews
                                • 3 BR
                                • 2 BA
                                • Sleeps 7
                                16
                                  NEW!
                                  • 2 BR
                                  • 1 BA
                                  • Sleeps 5
                                  1 Review
                                    NEW!
                                    • 1 BR
                                    • 1 BA
                                    • Sleeps 2
                                    1 Review
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 2
                                      3
                                        • 3 BR
                                        • 2 BA
                                        • 1 HF BA
                                        • Sleeps 8
                                          • 3 BR
                                          • 1 BA
                                          • 1 HF BA
                                          • Sleeps 6
                                          17
                                            • 4 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 12
                                              NEW!
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 6
                                                NEW!
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 6
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 2
                                                    • 1 BR
                                                    • 1 BA
                                                    • Sleeps 4
                                                      • 1 BR
                                                      • 1 BA
                                                      • Sleeps 2
                                                      17
                                                        • 1 BR
                                                        • 1 BA
                                                        • Sleeps 2
                                                        6
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 8
                                                          20
                                                            • 3 BR
                                                            • 1 BA
                                                            • Sleeps 8
                                                            1 Review
                                                              • 3 BR
                                                              • 3 BA
                                                              • Sleeps 9
                                                                NEW!
                                                                • 3 BR
                                                                • 1 BA
                                                                • 1 HF BA
                                                                • Sleeps 6
                                                                1 Review
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 6
                                                                  11
                                                                    • 1 BR
                                                                    • 1 BA
                                                                    • Sleeps 3
                                                                    2 Reviews
                                                                      • 4 BR
                                                                      • 1 BA
                                                                      • 1 HF BA
                                                                      • Sleeps 8
                                                                      35
                                                                        • 1 BR
                                                                        • 1 BA
                                                                        • Sleeps 5
                                                                        20
                                                                          • 2 BR
                                                                          • 1 BA
                                                                          • Sleeps 4
                                                                          11
                                                                            • 2 BR
                                                                            • 1 BA
                                                                            • Sleeps 4
                                                                            8
                                                                              • 2 BR
                                                                              • 1 BA
                                                                              • Sleeps 4
                                                                              14
                                                                                • 4 BR
                                                                                • 2 BA
                                                                                • Sleeps 8
                                                                                17
                                                                                  • 1 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 4
                                                                                  4
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    6
                                                                                      • 2 BR
                                                                                      • 1 BA
                                                                                      • Sleeps 6
                                                                                      16
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 6
                                                                                        13
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          2 Reviews
                                                                                            • 3 BR
                                                                                            • 1 BA
                                                                                            • Sleeps 5
                                                                                            16
                                                                                              • 5 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 6
                                                                                              2 Reviews
                                                                                                NEW!
                                                                                                • 2 BR
                                                                                                • 1 BA
                                                                                                • Sleeps 8
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • Sleeps 4
                                                                                                  9
                                                                                                    • 2 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 6
                                                                                                    33
                                                                                                      • 2 BR
                                                                                                      • 1 BA
                                                                                                      • Sleeps 6
                                                                                                      8
                                                                                                      • 1 - 50 of 120
                                                                                                       

                                                                                                      Recent Chesterfield Reviews

                                                                                                      Peace and nature

                                                                                                      5 of 5
                                                                                                      We had a beautiful, peaceful time at Djuna's place. It is so quiet, not even the sound of cars going by. Just a nice pond for swimming, a big yard, and a comfortable house. Like others have said, this is a peaceful refuge in nature . . . not a luxury rental. Djuna is easy to work with and very responsive if you need help. Her place was perfect for unwinding, and it's near Jacob's Pillow and the Lee outlets. Overall, just the pretty, serene week we were hoping for. Thanks, Djuna!
                                                                                                      • Submitted: Aug 28, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      home away from home

                                                                                                      5 of 5
                                                                                                      Our stay there was great. The apartment was clean and comfortable, the fridge was stocked well. After driving 1200 miles the last thing I wanted to do was grocery shopping. They had a great back yard with a pool. The wildlife was wild, if you are a bird lover you must put this place on your list. I would give Frank and his wife Manon 5 stars, thanks again for a great time.
                                                                                                      • Submitted: Aug 27, 2016
                                                                                                      • Stayed: Aug 2016

                                                                                                      Well appointed home, built by the owners who are masters of their craft.

                                                                                                      5 of 5
                                                                                                      We enjoyed a week in this quiet side of the Berkshires. Lee and Lenox are about a half hours drive, but the traffic was negligible over the tree lined (hilly!) roads. The kitchen was equipped sufficiently to eat meals at home, and the deck afforded a view of the woods beyond where coyotes roam, and bears are reputed to wander. The details of the home's construction were exceptional. The layout would be suitable for two couples for a long weekend. The second floor has a beautiful bathroom with a sunken tub, but no shower. It looks like a spa!
                                                                                                      • Submitted: Aug 25, 2016
                                                                                                      • Stayed: Aug 2016