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!

Narrow Results

Chestertown: Houses, Cabins & More (387)

  • 1 - 30 of 387
    • 3 BR
    • 3 BA
    • Sleeps 8
    6
    Request to Book View Details
    24 hrs Confirmation within 24 hours
      • 6 BR
      • 3 BA
      • Sleeps 20
      10
      Request to Book View Details
      24 hrs Confirmation within 24 hours
        • 3 BR
        • 2 BA
        • Sleeps 8
        4
        Request to Book View Details
        24 hrs Confirmation within 24 hours
          • 4 BR
          • 1 BA
          • Sleeps 7
          7
          Request to Book View Details
          24 hrs Confirmation within 24 hours
            • 6 BR
            • 4 BA
            • 1 HF BA
            • Sleeps 22
            Request to Book View Details
            24 hrs Confirmation within 24 hours
              • 5 BR
              • 2 BA
              • Sleeps 8
                • 4 BR
                • 4 BA
                • 1 HF BA
                • Sleeps 16
                1 Review
                Request to Book View Details
                24 hrs Confirmation within 24 hours
                  • 4 BR
                  • 3 BA
                  • 1 HF BA
                  • Sleeps 8
                  2 Reviews
                  Request to Book View Details
                  24 hrs Confirmation within 24 hours
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    4
                      • 4 BR
                      • 2 BA
                      • 1 HF BA
                      • Sleeps 10
                      1 Review
                        • 2 BR
                        • 2 BA
                        • Sleeps 8
                        2 Reviews
                          • 5 BR
                          • 2 BA
                          • Sleeps 12
                          Request to Book View Details
                          24 hrs Confirmation within 24 hours
                            • 2 BR
                            • 1 BA
                            • 1 HF BA
                            • Sleeps 7
                            4
                            Request to Book View Details
                            24 hrs Confirmation within 24 hours
                              • 6 BR
                              • 2 BA
                              • Sleeps 11
                              Request to Book View Details
                              24 hrs Confirmation within 24 hours
                                • 2 BR
                                • 2 BA
                                • Sleeps 6
                                  • 5 BR
                                  • 3 BA
                                  • 1 HF BA
                                  • Sleeps 10
                                  26
                                    • 6 BR
                                    • 3 BA
                                    • Sleeps 16
                                      • 5 BR
                                      • 3 BA
                                      • 2 HF BA
                                      • Sleeps 10
                                        • 4 BR
                                        • 2 BA
                                        • Sleeps 24
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 10
                                          3
                                          Request to Book View Details
                                          24 hrs Confirmation within 24 hours
                                            • 3 BR
                                            • 1 BA
                                            • 1 HF BA
                                            • Sleeps 6
                                            Request to Book View Details
                                            24 hrs Confirmation within 24 hours
                                              $117
                                              avg/night
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 5
                                              1 Review
                                              Request to Book View Details
                                              24 hrs Confirmation within 24 hours
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 6
                                                12
                                                Request to Book View Details
                                                24 hrs Confirmation within 24 hours
                                                  • 3 BR
                                                  • 2 BA
                                                  • Sleeps 9
                                                  25
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 5
                                                    2 Reviews
                                                    Request to Book View Details
                                                    24 hrs Confirmation within 24 hours
                                                      • 3 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 8
                                                      9
                                                        • 3 BR
                                                        • 3 BA
                                                        • Sleeps 7
                                                        3
                                                        Request to Book View Details
                                                        24 hrs Confirmation within 24 hours
                                                          • 3 BR
                                                          • 2 BA
                                                          • 1 HF BA
                                                          • Sleeps 8
                                                          1 Review
                                                          Request to Book View Details
                                                          24 hrs Confirmation within 24 hours
                                                            • 2 BR
                                                            • 1 BA
                                                            • Sleeps 5
                                                            5
                                                            Request to Book View Details
                                                            24 hrs Confirmation within 24 hours
                                                              • 2 BR
                                                              • 1 BA
                                                              • Sleeps 6
                                                              6
                                                              Request to Book View Details
                                                              24 hrs Confirmation within 24 hours
                                                              • 1 - 30 of 387
                                                               

                                                              Recent Chestertown Reviews

                                                              Great location, great house, and great experience.

                                                              5 of 5
                                                              We rented this house for a New Years Week get away. The home and the owners were terrific. The pictures on the site do not reflect how spacious this house actually is. We had 4 adults and 4 children under 12 and we were all very comfortable. We could tell that the sheets and the blankets were clean, so was the house. The house had everything we needed. It is private and quiet. The correspondence with the owner was outstanding. Thank you for a wonderful stay and for accommodating us for an extra night. We had so much fun, we didn't want to leave. I would really like to rent this home next time I am in the area.
                                                              • Submitted: Jan 10, 2016
                                                              • Stayed: Dec 2015

                                                              WONDERFUL IMMACULATE TOWNHOUSE WITH ALL AMENITIES

                                                              5 of 5
                                                              From the moment I was in contact with Joe, the owner of the townhouse, I knew it was going to be a great place. He was so accommodating and easy to communicate with. Everything that is posted in the listing is accurate and even better in person. We had all the comforts of home and couldn't have asked for anything more. We went skiing at Gore Mountain which is about a 20 minute drive from the townhouse. We took a day trip into Saratoga Springs and Ballston Spa (about 1 hour away). If you're into antiques, Ballston Spa had many great shops! We enjoyed time just relaxing in the home, renting movies, playing board games and sitting by the toasty fireplace. We can't wait to book another getaway with Joe & Dana in the near future! Thank you again for your warm hospitality!! Kathy, Tom and Family
                                                              • Submitted: Jan 5, 2016
                                                              • Stayed: Dec 2015

                                                              Great House, clean and what we were looking for. Thank you Nicole

                                                              5 of 5
                                                              Great property , quiet and restful
                                                              • Submitted: Jan 5, 2016
                                                              • Stayed: Dec 2015