Photo by Julie Miller

Search Hotels with a Bar in Chestertown

    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 Hotels with a Bar

Top Chestertown Hotels with a Bar

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

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (96)
"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 6.169.661 ₫
6.848.056 ₫ total
includes taxes & fees
18 Aug - 19 Aug
Friends Lake Inn
The Fern Lodge
Lake view

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (47)
"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 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.

Top Chestertown Hotel Reviews

Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 120 properties to choose from, and likely many will have a bar where you can enjoy an evening cocktail after exploring the city. While you're here, you can check out Loon Lake Beach and Friends Lake.
What is there to do in Chestertown?
Consider a visit to Loon Lake Beach, Friends Lake and Loon Lake, and then find a cosy 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 decide the best time for bar-hopping. 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.
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. If you'd like to venture out around the area, consider renting a car to explore more sights.