Find Hotels with Bars in Chestertown, MD

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Check availability on Chestertown Hotels with Bars

Our top choices for Chestertown hotels with a bar

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

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is AED 364
AED 416 total
includes taxes & fees
11 Dec - 12 Dec
The Lodge at Great Oak Landing
Reception
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (861)
"The breakfast was was very good with lots of options depending on your dietary needs."
United States
Terry
The price is AED 341
AED 378 total
includes taxes & fees
6 Jan - 7 January 2026
Hampton Inn Middletown
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

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
The price is AED 320
AED 355 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Lobby lounge
Courtyard Aberdeen at Ripken Stadium

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
The price is AED 309
AED 346 total
includes taxes & fees
28 Dec - 29 Dec
Courtyard Aberdeen at Ripken Stadium
Exterior
Hilton Garden Inn Aberdeen

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
The price is AED 320
AED 358 total
includes taxes & fees
26 Dec - 27 Dec
Hilton Garden Inn Aberdeen
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1907)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
Historic Inns of Annapolis
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (674)
"Great view, good ambiance all around"
United States
Dianne
The price is AED 426
AED 473 total
includes taxes & fees
21 Dec - 22 Dec
Hyatt Place Kent Narrows & Marina
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club

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
The price is AED 675
AED 843 total
includes taxes & fees
14 Dec - 15 Dec
The Inn at Chesapeake Bay Beach Club
Reception
Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (228)
"Friendly staff, clean hotel "
United States
Kelly
The price is AED 329
AED 369 total
includes taxes & fees
9 Jan - 10 January 2026
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

Residence Inn Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (106)
"The stay was perfect everyone was super kind and helpful and I will definitely be back "
United States
Katlynn
The price is AED 371
AED 416 total
includes taxes & fees
2 Jan - 3 January 2026
Residence Inn Aberdeen at Ripken Stadium
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

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Rooms were clean and staff was very friendly "
Shailesh 1-night trip
Posted 2 days ago
Hampton Inn Baltimore/Glen Burnie

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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.