A waterfront town with a pier, dock, and several buildings.

Compare and book 4 Star hotels in Chestertown, New York

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Check availability on Chestertown 4 Star Hotels

Our top choices for Chestertown 4-star hotels

Seasonal outdoor pool

Lodges At Cresthaven

Lodges At Cresthaven
4.0 star property
Lake George
9.4 out of 10, Exceptional, (619 reviews)
"The best place!"
United States
Allie
The price is 11.830.429 ₫
13.131.776 ₫ total
includes taxes & fees
26 Jul - 27 Jul
Lodges At Cresthaven
Luxury Studio Suite, 1 King Bed, Lake View (#1) | Lake view

Chateau Rooms

Chateau Rooms
4.5 star property
Bolton Landing
9.2 out of 10, Wonderful, (72 reviews)
"Our stay was incredible when we arrived we found out that our room got upgraded, and it was the most beautiful well kept cleaned and wonderful room with an amazing lake side view. Plus the location is impeccable, and it truly made our stay so much more memorable."
United States
Raquel
Chateau Rooms
Premier Room | 1 bedroom, premium bedding, iron/ironing board, free WiFi

Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.8 out of 10, Excellent, (110 reviews)
"Everything was clean and pretty and the staff was helpful and wonderful. Would go again"
United States
Jonathan
The price is 5.110.776 ₫
5.673.119 ₫ total
includes taxes & fees
21 Jul - 22 Jul
Friends Lake Inn
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Learn more about Chestertown

Nestled in the Adirondacks, this charming town offers hiking trails and kayaking on Friends Lake during summer months. Winter visitors can hit the slopes at nearby Gore Mountain in North Creek or explore the Natural Stone Bridge and Caves in Pottersville.

See all hotels in Chestertown
A snowy lodge with cabins and tall pine trees.
Photo by Julie Miller
Open Photo by Julie Miller

Top Chestertown Hotel Reviews

Frequently asked questions

What are the best 4-star hotels in Chestertown?
Make lifelong holiday memories in Chestertown at Friends Lake Inn. A favourite with Expedia customers, this 4-star hotel comes with lots of conveniences for a comfortable and relaxing stay.
How much does it cost to stay in a 4-star hotel in Chestertown?
To find a 4-star hotel in Chestertown that matches your budget, make use of Expedia's sort and search filters. Browse what's available during your holiday dates and use our pricing filter to set your limit. You can also sort your results by the most wallet-friendly escape first.

  • Search for the lowest price from 5.673.119 ₫

What's the difference between 5-star and 4-star hotels in Chestertown?
If you decide to holiday at a 4-star hotel in Chestertown, you'll usually find loads of conveniences to make sure you're comfortable, such as a gym, restaurant and pool. You can experience top-quality service and deluxe accommodation. Go for a 5-star hotel and you'll have access to a few more perks — think concierge assistance, on-site spas and indulgent turndown services. You're likely to get extra amenities and first-rate services at a 5-star stay, though both are awesome options for luxury guests.