Photo by Julie Miller

Find 4 Star Hotels in Chestertown, NY from SAR291

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Compare Chestertown 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Lodges At Cresthaven
Property grounds
Lodges At Cresthaven
4.0 star property
9.2 out of 10, Wonderful, (332)
"Excellent stay."
The price is SAR 990
SAR 1,092 total
includes taxes & fees
24 Sep - 25 Sep
Lodges At Cresthaven
Friends Lake Inn
Property entrance
Friends Lake Inn
4.0 star property
9.0 out of 10, Wonderful, (80)
"This hotel is beautiful, old style Adirondacks with cute rooms and great dining. While it is charming, the bed at least in the room I had was a springboard type of mattress you’d find at a koa camp. For the price to stay there I was shocked with it being one of the most uncomfortable sleeps I’ve gotten at any hotel and I travel a lot. Beds are an important piece to me. Aside from the super uncomfortable bed, the place was really nice. They didn’t skip on any Adirondack decor, the food for dinner...
The price is SAR 837
SAR 929 total
includes taxes & fees
24 Sep - 25 Sep
Friends Lake Inn
Chateau Rooms
Lake view
Chateau Rooms
4.5 star property
9.0 out of 10, Wonderful, (47)
"Wonderful setting and quiet environment"
Chateau Rooms
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Frequently asked questions

What are the best 4-star hotels in Chestertown?
Make lifelong vacation memories in Chestertown at Friends Lake Inn. A favorite 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 vacation 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 SAR291

What's the difference between 5-star and 4-star hotels in Chestertown?
If you decide to vacation 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 accommodations. 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.
Does Chestertown have any 4-star all-inclusive resorts?
Finding your dream vacation in Chestertown is as easy as entering your travel dates and selecting our “All inclusive” filter. Stay and play where everything is already taken care of like your room, meals and activities, or opt for a standard 4-star resort in or around this popular destination.
What are the top 4-star hotels in downtown Chestertown?
Enjoy the city sights effortlessly when you book a stay at Friends Lake Inn. Only 6 kilometers west from the heart of Chestertown, this 4-star hotel is the perfect location to make the most of this buzzing city with the added bonus of on-site ski equipment rental services and a garden.