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
3.5 star property
Chestertown
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
The Lodge at Great Oak Landing
Double Room, Ensuite (Haven) | Exterior

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
Haven Point Inn and Gallery
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (538 reviews)
"As always we loved our stay! Definitely will be coming back "
United States
John
Vandiver Inn
Reception

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (643 reviews)
"Quiet, clean, and friendly staff."
United States
William
Hilton Garden Inn Aberdeen
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (888 reviews)
"Great place to stay"
United States
Ken
Hampton Inn Middletown
Restaurant

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (227 reviews)
"Room were very clean, staff were excellent and friendly and helpful!"
United States
Matthew
Courtyard 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, (442 reviews)
"Very clean room, staff was very nice. "
United States
Byron
The Inn at Chesapeake Bay Beach Club
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,863 reviews)
"Great location "
United States
Betsy
Historic Inns of Annapolis
Bar (on property)

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (255 reviews)
"All staff friendly and professional "
United States
Kathleen
Hilton Garden Inn Bel Air
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (727 reviews)
"Clean hotel all around. Friendly stafff and comfortable environment."
United States
Jillian
Hyatt Place Kent Narrows & Marina
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

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Great hotel!"
James 1-night trip
Posted 5 hours ago
Pendry Baltimore

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Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 42 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: Comfort Inn & Suites Chestertown: Enjoy the bar, free WiFi, and room service. Historic Inns of Annapolis: Hotel with restaurant. Enjoy the 2 bars, free WiFi, and seasonal outdoor pool. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Hampton Inn Baltimore/Glen Burnie: Hotel with restaurant. Enjoy the bar, free WiFi, and rooftop terrace. 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 Northern Chesapeake Bay and 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.