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Find All-inclusive Resorts in Chestertown, NY

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Check availability on Chestertown All-inclusive Resorts

Our top choices for Chestertown all inclusive hotels

Premier Room | 1 bedroom, premium bedding, individually decorated
Friends Lake Inn

Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.6 out of 10, Excellent, (102)
"Friendly staff, room was clean, well maintained. Ate at the restaurant, food was great. "
United States
Erin
Friends Lake Inn
Exterior
Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins
2.0 star property
Chestertown
9.2 out of 10, Wonderful, (146)
"Excellent location and staff was very friendly."
United States
Logan
Pine Tree Motel & Cabins
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.
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Top Chestertown Hotel Reviews

Frequently asked questions

Looking for Chestertown all-inclusive resorts?
Chestertown is known for its natural setting and offers a host of things to see and do such as Loon Lake Beach and Friends Lake. Look through our choice of all-inclusive hotels where you can enjoy a range of amenities like entertainment, kid's clubs, and of course food and beverages all included in your stay. Many of our all-inclusive hotels also feature activities such as golf, yoga, water sports, and more, which you can enjoy without any additional expense.
What is there to do near my all-inclusive resort in Chestertown?
If you want to explore the area around your all-inclusive resort, visit Loon Lake Beach and Friends Lake and see why travelers like the natural setting in Chestertown. Other attractions include Loon Lake, Hudson River, and Tripp Pond.
When's the best time for an all-inclusive stay in Chestertown?
There's nothing like an all-inclusive vacation in Chestertown to rejuvenate you, especially when you know what to expect from the elements. Here's some info to help you choose when to book: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. January and February are the driest months while June and July are the rainiest months.

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