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Compare 409 Vacation Homes in Chestertown with updated reviews, rates, and availability.

"The house is absolutely beautiful and we fully enjoyed our time ! Thank you so much!"

"The house was beautiful, comfortable, and impressively well-appointed with creature comforts. There was tons of space, activities, and creature comforts. The lake was serene and the host was super responsive! We could not have asked for a better experience."

"Amazing view from the back deck, very clean home, plenty of room for our family of 6. Will definitely be staying here again next time we're in Lake George!"

"Excellent location! Minutes to restaurants and shops! Very nice rental! "

Enjoy sitting in hot tub , enjoying quiet country views.

"We were looking for something for our “baby moon” before I go back to work. We had a dream checklist and this home checked off everything on our list. We brought our 3mo old and our dog and had a peaceful weekend enjoying the hot tub, the Blackstone, and the cozy fireplace. We had some questions that were answered immediately. Can’t wait to go back with friends when it’s warmer not enjoy the pool and yard more! Love love lovd"

"The host was incredibly responsive to our questions and any issues we encountered. The house is perfect for gatherings with friends and family, offering plenty of activities on-site for all ages. The kitchen is well-stocked, making our stay enjoyable. We had a wonderful time!"

Front side of house as viewed from large private driveway

"Fantastic!! Cozy!!! gorgeous views! The whole experience was wonderful. Cannot wait to go back. Owner was very responsive!"

"The house is even better in person. So many beautiful amenities and we really enjoyed having a small shallow area to swim in. Ducks would often come right up to the dock. Beautiful firepit and grill area. Very accommodating host. We rented a boat and loved having a dock to keep it at overnight. It was a perfect house for a family vacation!"

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Other property types in Chestertown

"It was clean, nicely decorated, everything was new and in working order. Would suggest adding some face/wash cloths and top sheet for bed. Also, bed was comfortable but squeaked every time you made a move. All in all nice property and enjoyed our time :)"

"Better label of letter Q was hard to see at 10 pm getting there. Couldn’t use the kayak due to they were locked up. It was a beautiful weekend and that would have been nice to use them. Everything else was good. "