Photo by Julie Miller

Find Luxury 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 Luxury Hotels

Tonight
Jun 30 - Jul 1
Tomorrow
Jul 1 - Jul 2
This weekend
Jul 4 - Jul 6
Next weekend
Jul 11 - Jul 13

Top Chestertown Luxury Hotels

Frequently asked questions

Are you looking for a luxury hotel for your stay in Chestertown?
Use Expedia to arrange your flight to Glens Falls, NY (GFL-Floyd Bennett Memorial) airport, and then choose from a variety of places to stay that will deliver the luxury you seek. Amenities are an important consideration when you plan a vacation, so we make it easy to find what you'd like to make your stay special. If you want a posh hotel that has a spa, an indoor pool, or luxury bedding, Expedia can help you find the best luxury hotel experience that Chestertown has to offer. Chestertown has some interesting things to see and do including Friends Lake and Loon Lake, so you might want to take in the local sights during your visit.
What's the best luxury place to stay in Chestertown?
Friends Lake Inn is a 4-star hotel with a full-service spa and a terrace, and it's a popular choice for Expedia travelers looking for an elegant place to stay.
When can I expect good weather in Chestertown?
Planning for the weather is a good way to make your trip to Chestertown relaxing and enjoyable, especially when you're splurging. 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. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.
What's there to see and do in Chestertown?
Enjoy Chestertown and visit Friends Lake, Loon Lake, and Hudson River. If you have a little extra time during your trip, you might want to check out Loon Lake Beach and Tripp Pond.