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

4 Stars Hotels in Chestertown, New York from CA $287

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Check availability on Chestertown 4 Star Hotels

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

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, (621 reviews)
"Room Was clean and staff was friendly"
United States
peter
The price is CA $585
CA $649 total
includes taxes & fees
Aug 5 - Aug 6
Lodges At Cresthaven
Premier Room

Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.8 out of 10, Excellent, (112 reviews)
"Everything was clean and pretty and the staff was helpful and wonderful. Would go again"
United States
Jonathan
The price is CA $259
CA $287 total
includes taxes & fees
Jul 30 - Jul 31
Friends Lake Inn
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
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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

Find out more about Chestertown

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Chestertown are calling your name. Known for providing first-rate service in amazing locations, each of the Chestertown 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Chestertown. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Chestertown, New York, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Chestertown hotels with 4 Stars provide everything you need to unwind in style.

Frequently asked questions

What are the best 4-star hotels in Chestertown?
Relax in comfort at Friends Lake Inn. According to reviews by our guests, this is one of Chestertown's top 4-star hotels.
How much does it cost to stay in a 4-star hotel in Chestertown?
To book a 4-star hotel in Chestertown that matches your budget, use Expedia's filters. Check out the availability during your travel dates and use our pricing filter to set your limit. You can also list your results by the most economical retreat first.

  • Search for the lowest price from CA $287

What's the difference between 5-star and 4-star hotels in Chestertown?
Treat yourself to luxury living during your Chestertown getaway by staying at a 4-star hotel. As well as featuring upmarket accommodations, these properties are typically filled with amenities such as large beds, bathrobes and plenty more. A 5-star hotel will go above and beyond to make your trip an even more lavish and unforgettable one. 24-hour front desk, elegant furnishings and gourmet dining are just the start of the first-rate services and conveniences you'll likely get access to.

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