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Find Hotels with Bars in Chestertown, MD

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Check availability on Chestertown Hotels with Bars

Top Chestertown Hotels with Bars

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (768)
"The breakfast was consistently tasty."
The price is AED 415
AED 460 total
includes taxes & fees
15 Jun - 16 Jun
Comfort Inn & Suites Chestertown
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.

Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 45 hotels and other accommodations to choose from, and likely many will have a bar where you can unwind with a late-night cocktail. While you’re here, consider a visit to Historical Society of Kent County Maryland and Rolphs Wharf Marina.
What are the best hotels with bars in Chestertown?
Here are some favorite hotels with bars in and around Chestertown: Red Roof Inn & Suites Chestertown: Lodge with restaurant. Enjoy the 3 bars, free WiFi, and free parking. Comfort Inn & Suites Chestertown: Enjoy the bar, free WiFi, and room service. The Lodge at Great Oak Landing: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Historic Inns of Annapolis: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Best Western Plus Hotel & Conference Center: Hotel with restaurant. Enjoy the 2 bars, free WiFi, and seasonal outdoor pool.
What is there to do in Chestertown?
In the area, you can visit Historical Society of Kent County Maryland, Rolphs Wharf Marina, and Betterton Beach, then find a cozy spot for a nightcap. Other places to see include Garfield Center for the Arts at the Prince Theater and Chestertown Historic District.
When is the best time to visit Chestertown?
Visiting local bars in Chestertown is better when you know what the weather holds. These temperatures and rainfall averages can help you determine the best time for bar hopping. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
How can I get to Chestertown and around the area?
You might want to make the most of these transportation options in and around Chestertown: Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city center. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you’d like to explore around the area, consider renting a car to take in more sights.