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Find Hotels with Bars in Chestertown, MD

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Check availability on Chestertown Hotels with Bars

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

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (758)
"Staff was efficient and very helpful. Clean room with microwave & fridge - well stocked linens in bathroom - great breakfast - thank you for a comfortable stay."
The price is SAR 411
SAR 456 total
includes taxes & fees
11 May - 12 May
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.
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Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 44 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: Hotel with restaurant. Enjoy the bar, free WiFi, and room service. The Lodge at Great Oak Landing: Hotel with restaurant. Enjoy the 2 bars, free WiFi, and seasonal outdoor pool. Historic Inns of Annapolis: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Sagamore Pendry Baltimore: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking.
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 Urieville Park.
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.