Photo by Julie Miller

Search Chalets in Chestertown

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 16 Chalets in Chestertown with updated reviews, rates, and availability.

Private Chalet In NW Bay With 25 Foot Dock!!

10.0 out of 10, Exceptional, (112)
"We loved our stay here and the location was perfect to view the lake and access all of the outdoor activities we could ask for! Patti was so accommodating letting us take our dog with us and even left us a bowl of puppy treats! All the little touches when we first walked in created such a great impression, cookies on a platter for us, some wine to ring in the new year, lit candles, handwritten notes, stocked firewood, and all of the winter and holiday decor to make us feel special. The chalet is...
Private Chalet In NW Bay With 25 Foot Dock!!

Adirondack “River Rapture"- Lake George/Mount Gore

10.0 out of 10, Exceptional, (33)
"This property is amazing. The pictures are accurate and a great spot. The house is everything you would want in the Adirondacks. The location was convenient to so much. The owners are very helpful if needed and very friendly. The house is a must if traveling to the area."
Adirondack “River Rapture"- Lake George/Mount Gore

Lake Front Chalet

10.0 out of 10, Exceptional, (7)
"This was out first time at this amazing property. Scenic views of the lake from the comfortable couches on the deck. There was a lot to do, kayaks and paddle boat supplied. You can easily walk into the lake and swim to the float. The house itself was wonderful. The bed was very comfortable as was the couch. Everything was very clean with modern appliances and decor was very inviting. We will definitely be returning to this haven on the lake!"
Lake Front Chalet

Bolton Landing Mountain House!

8.8 out of 10, Excellent, (6)
"Exactly what a group of 4 friends needed. "
The price is SAR 1,874
SAR 3,504 total
includes taxes & fees
6 Jan - 7 Jan
Bolton Landing Mountain House!

A Private Chalet in the Adirondacks that feels like home w/a standby Generator!

10.0 out of 10, Exceptional, (95)
"We are very impressed and want to stay again. "
A Private Chalet in the Adirondacks that feels like home w/a standby Generator!

Birch Hill Lodge, Amazing chalet near Gore Mountain w/hot tub, playroom, fireplace

10.0 out of 10, Exceptional, (10)
"We stayed last weekend at this beautiful house. Everything was as advertised and better. Our resident chef was impressed by the high end kitchen appliances and cookware. There were six of us and plenty of room to spread out. The hot tub, the pool, the game room, the deck, the fire pit. Something for everyone. The hot tub was the perfect temperature and the pool was, too! We had a fantastic dinner we cooked on the grill and ate at the large dining table. Lots of laughter and leisure. Highly...
Birch Hill Lodge, Amazing chalet near Gore Mountain w/hot tub, playroom, fireplace

Lake George/ Gore / snowmobile trail access NEW HOME

10.0 out of 10, Exceptional, (11)
"Great place to stay. Convenient to lake george but away from the craziness of town. The home is beautiful with plenty of space and parking. Very clean. The homeowner even gave some excellent recommendations for pizza and a local swimming hole!"
Lake George/ Gore / snowmobile trail access NEW HOME

Loon Lake, Chestertown - Spotless, bright chalet, sleeps 6-8, near public beach

10.0 out of 10, Exceptional, (84)
"We had a wonderful time at Haus Kronov. It's large, clean and stocked perfectly. The covered porch and the huge deck are game changers."
Loon Lake, Chestertown - Spotless, bright chalet, sleeps 6-8, near public beach

3 BR Adirondack Beach House with a spacious loft near the beach and water views!

8.6 out of 10, Excellent, (14)
"Definitively a go!"
3 BR Adirondack Beach House with a spacious loft near the beach and water views!

Lake George Secluded Chalet: Terrace, Firepit, BBQ Grill, Foosball, Air Hockey

10.0 out of 10, Exceptional, (2)
"Had a great time. The host Katie was remarkably responsive. Beautiful property and very close to town. Super easy check-in/check-out. "
Lake George Secluded Chalet: Terrace, Firepit, BBQ Grill, Foosball, Air Hockey

Tucked Away in ADKs - Minutes from Gore

10.0 out of 10, Exceptional, (4)
"We had a great time staying at the property in North Creek! The house was very clean and spacious, the hosts were very communicative, the location was great (just 30 minutes away from Lake George, 10 minutes from Lake Minerva and a3 minutes away from charming downtown North Creek). Highly recommend and will stay again when traveling to the area!"
Tucked Away in ADKs - Minutes from Gore

Cozy Chalet on Mill Creek

10.0 out of 10, Exceptional, (7)
"This house was perfect for our stay!!! ( 4 “ Senior” adults. It was secluded, soothing creek along back of property but easy to travel to Saratoga Springs Race track, Ft Ticonderoga, Lake George, several nearby town with great restaurants and —-ice cream!! House was roomy, clean, fully stocked and comfortable beds. Lots of natural and artificial light!"
Cozy Chalet on Mill Creek

Balsam Point Lake House a Lakeside Getaway for Family Fun and Relaxation.

10.0 out of 10, Exceptional, (4)
"Enjoyed hiking Castle Rock and Sawyer Mt trails nearby. Visited the Adirondack Experience history Museum on a rainy afternoon. If you enjoy the outdoor it’s a great retreat! We brought plenty of food and enjoyed the charcoal grill every night. Very private and relaxing! Very much enjoyed our stay here!"
Balsam Point Lake House a Lakeside Getaway for Family Fun and Relaxation.

Lake George Chalet - The Pines Chickadee #29

10.0 out of 10, Exceptional, (2)
"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."
Lake George Chalet - The Pines Chickadee #29

Gore Mountain Chalet - 5 Minutes to Gore Mountain - 4 Bedrooms

Gore Mountain Chalet - 5 Minutes to Gore Mountain - 4 Bedrooms

Chalet on Private Alderbrook Lake

2.0 star property
Chalet on Private Alderbrook Lake
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Chestertown
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chestertown

Peaceful Lakeside Retreat with Private Beach

9.2 out of 10, Wonderful, (17)
"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 :)"
Peaceful Lakeside Retreat with Private Beach

Cozy retreat with fireplace, kayaks, and shared beach/pond access

9.0 out of 10, Wonderful, (16)
"Beautiful place wood location"
Cozy retreat with fireplace, kayaks, and shared beach/pond access

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (55)
"It’s a wonderful place beautiful fireplace cozy cabin. Bed is so comfy. Just know there is only one bathroom but it’s big and nice. Worth the stay. "
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.