Find Hotels with Bars in Chestertown, MD

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Top Chestertown Hotels with Bars

Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 star property
Chestertown
8.0 out of 10, Very Good, (76)
"Very nice rooms, "
United States
Stephania
$113 nightly
The price is $126
Dec 8 - Dec 9
Total with taxes and fees
The Lodge at Great Oak Landing
Exterior
Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen

3.0 star property
Aberdeen
8.6 out of 10, Excellent, (631)
"Close to restaurants, friendly staff, nice room, food was great"
United States
Peggy
$87 nightly
The price is $97
Dec 18 - Dec 19
Total with taxes and fees
Hilton Garden Inn Aberdeen
Reception
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
8.8 out of 10, Excellent, (860)
"Enjoyed the amenities and great location for shops nearby "
United States
Erica
$93 nightly
The price is $103
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hampton Inn Middletown
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
9.2 out of 10, Wonderful, (930)
"nice, clean, up to date, budget friendly hotel"
United States
mike
$79 nightly
The price is $88
Dec 18 - Dec 19
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Lobby lounge
Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium

3.0 star property
Aberdeen
8.6 out of 10, Excellent, (216)
"We reserved 4 rooms, and arrived around noon. We didn't think, with early arrival, that our rooms would be ready, but they were! The staff was extremely accommodating and friendly. Our rooms were immaculate, beds comfy. It was a great stay for visiting family in the area. "
United States
Stephen
$84 nightly
The price is $94
Dec 23 - Dec 24
Total with taxes and fees
Courtyard Aberdeen at Ripken Stadium
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.6 out of 10, Exceptional, (673)
"Great view, good ambiance all around"
United States
Dianne
$116 nightly
The price is $129
Dec 14 - Dec 15
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1903)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
$144 nightly
The price is $164
Jan 1 - Jan 2, 2026
Total with taxes and fees
Historic Inns of Annapolis
Reception
Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air

3.0 star property
Bel Air
9.2 out of 10, Wonderful, (227)
"Friendly staff, clean hotel "
United States
Kelly
$95 nightly
The price is $107
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Bel Air
Premium bedding, in-room safe, desk, iron/ironing board
Residence Inn Aberdeen at Ripken Stadium

Residence Inn Aberdeen at Ripken Stadium

3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (106)
"The view from our room of the Cal Ripkin complex was amazing. "
United States
Christopher
$101 nightly
The price is $113
Dec 29 - Dec 30
Total with taxes and fees
Residence Inn Aberdeen at Ripken Stadium
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4.0 star property
Stevensville
9.4 out of 10, Exceptional, (429)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
$207 nightly
The price is $230
Dec 10 - Dec 11
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
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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Top Chestertown Hotel Reviews

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"The room was exll"
Anthony 1-night trip
Posted 1 day ago
Hilton Garden Inn Baltimore/White Marsh

Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 38 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 Chestertown Historic District.
What are the best hotels with bars in Chestertown?
Here are some favorite hotels with bars in and around Chestertown: Comfort Inn & Suites Chestertown: Lodge with restaurant. Enjoy the 3 bars, free WiFi, and free parking. Red Roof Inn & Suites Chestertown: Hotel with restaurant. Enjoy the 2 bars, free WiFi, and seasonal outdoor pool. The Lodge at Great Oak Landing: Enjoy the bar, free WiFi, and room service. Pendry Baltimore: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: 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, Chestertown Historic District, and Rolphs Wharf Marina, then find a cozy spot for a nightcap. Other places to see include Crumpton Auction and Northern Chesapeake Bay.
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.

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