Photo by Julie Miller

Find All Inclusive Resorts and Hotels in Chestertown, NY

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown All Inclusive Resorts and Hotels

Tonight
Aug 5 - Aug 6
Tomorrow
Aug 6 - Aug 7
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Chestertown All Inclusive Resorts and Hotels

Friends Lake Inn
Relax in this inviting bedroom with a large bed, stone fireplace, and mounted TV.

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (94)
"Very nice location. Would have enjoyed more activity like hiking or a pool or something on site. But it met our requirements for a beautiful place to stay with good food"
The price is CA $307
CA $341 total
includes taxes & fees
Aug 6 - Aug 7
Friends Lake Inn
Pine Tree Motel & Cabins
Cabins with front porches and lawns set amidst dense coniferous trees.

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (133)
"Excellent location and staff was very friendly."
The price is CA $241
CA $268 total
includes taxes & fees
Aug 6 - Aug 7
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.

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.