Search Chalets in Chestertown from CA $600

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Browse Select Chestertown Chalets

Escape to a serene cabin surrounded by trees and a rock formation, offering a peaceful retreat.

"This home was an ideal space for our group! The games and firepit were a hit; very little time spent using technology is always a win! The space was cozy and welcoming, we'd love to visit again."

Relax on the enclosed porch with a table, chairs, and a comfortable seating area.

"A very clean and cozy place to stay. The owners are the nicest folks you can imagine. We will be booking again when we return."

Escape to a serene winter retreat surrounded by snow-covered trees and a tranquil atmosphere.

"The house was very clean and a great layout and location! Would stay again!!"

Enjoy a peaceful retreat in this charming single-story house with a covered porch and lush surroundings.

"Had a peaceful time staying here and it’s not to far from gore mountain for a ski trip."

Stunning two-story building with a gabled roof, set amidst a beautifully maintained garden.

"The house is clean, comfortable, great for large groups, and the view is amazing. Highly recommend! "

Escape to a secluded cabin surrounded by tall trees, with a cozy porch and a large rock in the front yard.

"We came to ski Gore. 5 of us. 2 grandparents, 1 adult and 2 grandchildren ages 8&9. Perfect place to stay after the slopes. Loved the fireplace. Kitchen was well equipped. House was clean and comfortable for our group. Would stay again for sure"

Enjoy the forest views from the cabin's welcoming deck with Adirondack chairs.

"Amazing home, well appointed and all the comforts and then some. Private, beautiful, scenic with access to the Schroon River! So close to the lovely town of Bolton Landing we loved every moment!"

CA $1,111 total

includes taxes & fees

Aug 24 - Aug 25

Enjoy a serene view of the surrounding winter landscape from this deck.

"Amazing location on a beautiful and peaceful lake. Very private and well stocked. Kayaks and paddleboards available for use. Less than 2 miles from local restaurant and shops."

Escape to a serene forest retreat with a cozy cabin featuring a spacious deck and a charming staircase.

"Overall the property was clean and tidy for our arrival. Upstairs area perfect for children/extra guests but my partner and I enjoyed the one downstairs just fine. Stairs may be a bit tough for those with walking issues (they are a bit narrow) but otherwise not bad for some 20-somethings like us! Easy access to restaurants/attractions up and down the lake and the pool was nicely kept too."

Guests can enjoy a cozy cabin-style retreat with a spacious deck and fireplace.

"We had a nice stay among the trees and found fun things to do in town. "

Relax by the serene lake with a dining area under a shaded umbrella, surrounded by lush greenery and a tranquil atmosphere.

"Exactly as advertised. Great location and accommodating hosts."

"Great property just a short drive away from Gore Mountain. Even in the middle of a snow storm the hosts made sure everything was taken care of. Highly recommend! "

Situated in a natural setting, this lodge features a large window and a door with a green frame, surrounded by a well-maintained lawn and trees.

"A fantastic property for a group ranging from kids 2-9 and adults. The property had all we needed and plenty of space to play and hang out."

Situated in a forested area, this cabin offers a cozy retreat with a balcony and fire pit.

"Place was beautiful. Located near Gore mountain and many things to do."

Escape to a serene retreat surrounded by nature, with a cozy cabin-style lodging featuring a front porch and picnic areas.

"Stayed for one night in the Bay Harbor Suite with friends. Loved the use of all the water toys and a great view!"

Adorned with festive lights, this charming house features a unique triangular structure and a cozy porch area.

Relax on the deck with a glass-top table and two comfortable chairs, shaded by a large umbrella.

"A relaxing month in a beautiful country setting. The owner was very responsive to all of our needs. The house and kitchen had all the necessary equipment and supplies."