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!

Chestertown: Houses, Cabins & More (382)

  • 1 - 50 of 382
    • 2 BR
    • 1 BA
    • 1 HF BA
    • Sleeps 7
    6
      • 3 BR
      • 3 BA
      • Sleeps 8
      8
        • 4 BR
        • 2 BA
        • Sleeps 12
        4
          • 3 BR
          • 2 BA
          • Sleeps 10
          5
            • 6 BR
            • 3 BA
            • Sleeps 20
            11
              • 3 BR
              • 2 BA
              • 1 HF BA
              • Sleeps 8
              12
                • 2 BR
                • 2 BA
                • Sleeps 8
                  • 2 BR
                  • 1 BA
                  • Sleeps 5
                  6
                    • 2 BR
                    • 2 BA
                    • 1 HF BA
                    • Sleeps 8
                    11
                      • 1 BR
                      • 1 BA
                      • Sleeps 6
                      6
                        • 2 BR
                        • 2 BA
                        • Sleeps 4
                        5
                          • 2 BR
                          • 1 BA
                          • Sleeps 6
                          12
                            • 3 BR
                            • 2 BA
                            • Sleeps 8
                            10
                              • 3 BR
                              • 2 BA
                              • Sleeps 6
                              6
                                • 2 BR
                                • 1 BA
                                • Sleeps 6
                                16
                                  • 3 BR
                                  • 3 BA
                                  • Sleeps 6
                                  5
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 8
                                    9
                                      • 4 BR
                                      • 2 BA
                                      • Sleeps 10
                                      4
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 5
                                        3
                                          • 3 BR
                                          • 2 BA
                                          • 1 HF BA
                                          • Sleeps 6
                                          2 Reviews
                                            • 4 BR
                                            • 1 BA
                                            • Sleeps 7
                                            8
                                              • 3 BR
                                              • 3 BA
                                              • Sleeps 7
                                              6
                                                • 4 BR
                                                • 2 BA
                                                • 1 HF BA
                                                • Sleeps 8
                                                  • 4 BR
                                                  • 1 BA
                                                  • Sleeps 7
                                                  1 Review
                                                    • 4 BR
                                                    • 4 BA
                                                    • 1 HF BA
                                                    • Sleeps 16
                                                    1 Review
                                                      • 3 BR
                                                      • 2 BA
                                                      • 1 HF BA
                                                      • Sleeps 6
                                                      2 Reviews
                                                        • 2 BR
                                                        • 1 BA
                                                        • Sleeps 5
                                                        4
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 4
                                                          2 Reviews
                                                            • 8 BR
                                                            • 2 BA
                                                            • 1 HF BA
                                                            • Sleeps 16
                                                            13
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 10
                                                                • 2 BR
                                                                • 1 BA
                                                                • Sleeps 6
                                                                4
                                                                  • 4 BR
                                                                  • 3 BA
                                                                  • Sleeps 14
                                                                  3
                                                                    • 4 BR
                                                                    • 4 BA
                                                                    • Sleeps 13
                                                                    4
                                                                      • 4 BR
                                                                      • 1 BA
                                                                      • Sleeps 8
                                                                        • 3 BR
                                                                        • 3 BA
                                                                        • Sleeps 8
                                                                        1 Review
                                                                          • 3 BR
                                                                          • 2 BA
                                                                          • Sleeps 8
                                                                            • 5 BR
                                                                            • 2 BA
                                                                            • Sleeps 8
                                                                            6
                                                                              • 5 BR
                                                                              • 3 BA
                                                                              • Sleeps 12
                                                                              9
                                                                                • 2 BR
                                                                                • 2 BA
                                                                                • Sleeps 5
                                                                                  • 2 BR
                                                                                  • 1 BA
                                                                                  • Sleeps 6
                                                                                  4
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    14
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 10
                                                                                        • 4 BR
                                                                                        • 3 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 12
                                                                                        18
                                                                                          • 3 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 12
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 10
                                                                                            6
                                                                                              • 4 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 12
                                                                                                • 5 BR
                                                                                                • 3 BA
                                                                                                • Sleeps 12
                                                                                                12
                                                                                                  • 12 BR
                                                                                                  • 12 BA
                                                                                                  • Sleeps 36
                                                                                                    • 4 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 10
                                                                                                    45
                                                                                                    • 1 - 50 of 382
                                                                                                     

                                                                                                    Recent Chestertown Reviews

                                                                                                    Cute cozy condo!

                                                                                                    5 of 5
                                                                                                    We loved this place! It was the cutest condo. I love the "cabin feel" it had and it was the perfect amount of space for us and our 2 kids. It was clean/well maintained. All the neighbors were nice and it was perfect having the outdoor fire place. Having Tripp Lake right there to use was awesome too and we totally took advantage. Plus, it's a short 15 min drive into Lake George. Couldn't have been happier with the location.
                                                                                                    • Submitted: Aug 25, 2016
                                                                                                    • Stayed: Aug 2016

                                                                                                    Lovely Adirondack Retreat

                                                                                                    4 of 5
                                                                                                    This house was beautiful and very clean. The pictures provided are a very accurate description of what to expect from the house. There’s so much space, inside & out. We thought the location was great with a short walk to Brant Lake, and a short drive to Lake George. The property manager and owner were very accommodating. We had to contact the property manager a few times and she answered promptly every time. The owner even let us park at his house which is directly across from the lake. This was great for getting the kayaks down, as well as children and senior citizens. The only reason I am leaving 4 stars instead of 5 is b/c of the heat. Unfortunately for us, we chose a weekend that happened to be the hottest of the year. We know that is out of everyone’s control, but we just wish more was done to battle that heat. It would’ve helped a lot if there were at least curtains on the windows to block the heat. We were able to work something out, but it was uncomfortable for a little bit. I did notice some complaints from previous renters that we just did not see. We didn’t think the house was sparsely furnished. What we needed was there, and it was completely fine. We saw no issues with the lighting in the house. There were some discrepancies on certain amenities listed, but those items were cleared up before we went up there. The upstairs shower is small and works better as a tub than a shower, but I felt that was shown in the pictures so we expected that before we went up. It is the first year this house is rented, so I’m sure any issues that may arise will be worked out, especially since we continually saw prompt accommodating responses. All in all, we really enjoyed the house, and had a great vacation. I would recommend others to stay here.
                                                                                                    • Submitted: Aug 23, 2016
                                                                                                    • Stayed: Aug 2016

                                                                                                    Great Family Vacation

                                                                                                    5 of 5
                                                                                                    GREAT FAMILY VACATION Our family of 5 REALLY enjoyed this condo! We all slept great in it because we felt so at home and it was so quiet and peaceful! Everything about the condo was excellent- it was clean, organized, cozy, and functional while also beautifully decorated! It is a very short walk to Tripp lake and our kids spent hours there swimming out to the float, kayaking and making sandcastles. We loved the scenery and solitude while only being 20 min away from Lake George and all the action. We went parasailing, on a steam boat ride, to Fort William Henry, to water slide world, and mini golfing. We enjoyed meals on the screened in porch and meals out as there are tons of choices for restaurants. We hope to visit again and explore even more!
                                                                                                    • Submitted: Aug 22, 2016
                                                                                                    • Stayed: Aug 2016