Photo by Julie Miller

Find Hotels with Bars in Chestertown, NY

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

Friends Lake Inn
Property entrance

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (84)
"Great room, very nice staff. Nice weekend getaway."
The price is SAR 837
SAR 929 total
includes taxes & fees
26 Dec - 27 Dec
Friends Lake Inn
The Fern Lodge
Room

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (45)
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."
The price is SAR 2,249
SAR 2,496 total
includes taxes & fees
6 Jan - 7 January 2025
The Fern Lodge
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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Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 116 hotels and other accommodations to choose from, and likely many will have a bar where you can enjoy an evening cocktail after a day out exploring. While you’re here, you can check out Loon Lake Beach and Friends Lake.
What are the best hotels with bars in Chestertown?
Here’s some of the top Chestertown accommodations with bars: Friends Lake Inn: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. The Fern Lodge: Enjoy the bar, free breakfast, and free WiFi.
What is there to do in Chestertown?
Consider a visit to Loon Lake Beach, Friends Lake, and Loon Lake, and then find a cozy spot for a nightcap. Other places to see include Hudson River and Tripp Pond. Chestertown is known for its lakeside.
When is the best time to visit Chestertown?
Visiting local bars in Chestertown is more fun when you know what the weather holds. These rainfall averages and temperatures can help you determine the best time for bar hopping. 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.
How can I get to Chestertown and around the area?
Here are some of your transportation options in and around Chestertown: Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), which is located 23.6 mi (38 km) away from the heart of the city. If you’d like to venture out around the area, you may want to rent a car for your trip.