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Find Luxury Hotels in Chestertown

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Check availability on Chestertown Luxury Hotels

Tonight
26 Jul - 27 Jul
Tomorrow
27 Jul - 28 Jul
Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug

Top Luxury Hotels in Chestertown

Top Chestertown Hotel Reviews

Lakefront Terrace Resort

Lakefront Terrace Resort

10/10 Excellent
"I like that its lake front. Food was excellent. Staff were very friendly."
Arlene 3-night trip
Posted 23 hours ago
Lakefront Terrace Resort

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 holiday, 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 Loon Lake Beach and Friends Lake, so you might want to take in the local sights during your visit.
What's the best luxury hotel 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 travellers 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 temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chestertown are January, March, November and December, with each month seeing an average of 33 cm of snowfall.
What's there to see and do in Chestertown?
Enjoy Chestertown and visit Loon Lake Beach, Friends Lake and Loon Lake. If you have a little extra time during your trip, you might want to check out Hudson River and Tripp Pond.