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: Budget Vacation Rentals (37)

  • 1 - 37 of 37
Additional fees apply. Taxes may be added.
    • 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
          • 1 BA
          • Sleeps 6
          12
            • 3 BR
            • 2 BA
            • Sleeps 8
            10
              • 2 BR
              • 1 BA
              • Sleeps 5
              4
                • 4 BR
                • 3 BA
                • 1 HF BA
                • Sleeps 12
                18
                  • 2 BR
                  • 1 BA
                  • Sleeps 6
                  2 Reviews
                    • 2 BR
                    • 2 BA
                    • Sleeps 4
                    3
                      • 3 BR
                      • 3 BA
                      • 1 HF BA
                      • Sleeps 6
                        • 3 BR
                        • 2 BA
                        • Sleeps 8
                        8
                          • 5 BR
                          • 2 BA
                          • Sleeps 11
                          4
                            • 1 BR
                            • 1 BA
                            • Sleeps 6
                              • 3 BR
                              • 2 BA
                              • Sleeps 8
                              6
                                • 5 BR
                                • 3 BA
                                • Sleeps 12
                                33
                                  • 1 BR
                                  • 1 BA
                                  • Sleeps 4
                                    • 3 BR
                                    • 1 BA
                                    • Sleeps 6
                                    11
                                      • 1 BR
                                      • 1 BA
                                      • Sleeps 4
                                        • 2 BR
                                        • 1 BA
                                        • Sleeps 6
                                          • 3 BR
                                          • 2 BA
                                          • Sleeps 9
                                          5
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 8
                                            5
                                              • 6 BR
                                              • 3 BA
                                              • Sleeps 16
                                              1 Review
                                                • 2 BR
                                                • 1 BA
                                                • Sleeps 8
                                                3
                                                  • 1 BR
                                                  • 1 BA
                                                  • Sleeps 4
                                                  6
                                                    • 4 BR
                                                    • 1 BA
                                                    • Sleeps 8
                                                    4
                                                      • 4 BR
                                                      • 2 BA
                                                      • Sleeps 9
                                                      2 Reviews
                                                        • 2 BR
                                                        • 2 BA
                                                        • Sleeps 5
                                                        3
                                                          • 2 BR
                                                          • 1 BA
                                                          • Sleeps 6
                                                            • 5 BR
                                                            • 2 BA
                                                            • Sleeps 12
                                                            6
                                                              • 4 BR
                                                              • 2 BA
                                                              • Sleeps 6
                                                              11
                                                                • 2 BR
                                                                • 2 BA
                                                                • Sleeps 7
                                                                22
                                                                  • 2 BR
                                                                  • 1 BA
                                                                  • Sleeps 7
                                                                  6
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • Sleeps 10
                                                                    3
                                                                      • 1 BR
                                                                      • 1 BA
                                                                      • Sleeps 6
                                                                      14
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 5
                                                                        1 Review
                                                                        • 1 - 37 of 37
                                                                         

                                                                        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

                                                                        If you like peace and quiet...this is the place for you!

                                                                        5 of 5
                                                                        First, I have to say the owners were amazing. Bob was easy to contact and offered answers to all questions I had....right away. My family has been coming to the Lake George area for years. Often times, Lake George Village is a lot of action and people. Can get a bit busy. We wanted more woods, lake, small town, quiet and peacfulnes. We traveled more north on Rt.9...we discovered the town of Bolton Landing and Diamond Point. Locals are amazing. Make you feel right at home in the small cozy town. Love to eat out overlooking lake and renting boats for the day. I found Bob's beautiful cabin online. My husband was not happy we me booking something online...but the minute we drove down the private road and approached the cabin he looked and me and said "this is amazing...you did good". I told Bob what we were looking for and his cabin checked all it boxes. There is a small community on Trout Lake. Only 5 minutes from Lake George. It is stunning. The cabin overlooks the lake. I mean its you, deck, some grassy area and then the Lake...literally all to yourself. There was not a cup of coffee or glass of wine not had from Bob's deck or dock. The dock was huge. We had a party of 8, 4 adults and 4 children. No one was bored or disappointed. Kids fished daily and actually caught some decent fish. Dock loaded with lounges. We used all fun equipment from floats, extra swim dock and even kayaks. First time we did kayaks and it's so relaxing. The dock was a place to relax, chat and enjoy everything around you. The cabin was cozy and had everything needed. We came up with our linens (which you don't have to bring) and our food. I must say a charcoal grill makes the food taste so much better. The deck off the cabin had two rocking Adirondack chairs that you saw sun come and down. Candles lit and enjoyed fire pit, smores and family time. If you are looking to travel to Lake George area, want a reliable owner who loves his property and has everything you need for a peaceful vacation contact Bob. You won't be disappointed...I promise you.!
                                                                        • Submitted: Aug 21, 2016
                                                                        • Stayed: Aug 2016

                                                                        Just What We've Been Looking For

                                                                        5 of 5
                                                                        This was our 5th summer vacation week in LG and we've finally found a place to stay that suits us completely.The Boardwalk Cottage really has it all. First impression was that the cottage is so well maintained and so clean. Terri obviously cares about providing a quality place for vacationers. The bathrooms were recently updated and clean. Bedrooms have very comfortable beds and the air conditioners keep everything comfortable. My family slept so well all week.The kitchen was fully stocked with all that we needed. A gas grill on the patio (which is also very nice) allowed us to stay put for dinner most nights. The location is another plus. Right within walking distance to the beach (307 "little" steps according to my daughter), Shepard Park, the grocery store, the heart of the village, restaurants, shopping and just about everything you need. The Cottage was just the right place for our family of 4, but I believe that a family of 5-7 would be just as comfortable. Terri is great to work with and the staff at the Marina really makes you feel like you are at home. Needless to say, I highly recommend that you consider staying at the Cottage. We'll be returning again next summer.
                                                                        • Submitted: Aug 21, 2016
                                                                        • Stayed: Aug 2016