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 price is AED 397
AED 454 total
includes taxes & fees
16 Mar - 17 Mar
The Lodge at Great Oak Landing
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, (971 reviews)
"Check-in was great! The young man at the desk was so friendly and helpful!! Room was clean and beds were clean and comfortable!"
United States
Kelley
The price is AED 404
AED 448 total
includes taxes & fees
31 Mar - 1 Apr
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (536 reviews)
"a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back"
United States
Dieter
Vandiver Inn
Terrace/patio

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,001 reviews)
"Staff was friendly and rooms were clean. Beautiful area to visit. "
United States
Amy
The price is AED 419
AED 465 total
includes taxes & fees
16 Mar - 17 Mar
Hilton Garden Inn Kent Island Marina
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (883 reviews)
"Great place to stay"
United States
Ken
The price is AED 362
AED 402 total
includes taxes & fees
31 Mar - 1 Apr
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, (226 reviews)
"Room were very clean, staff were excellent and friendly and helpful!"
United States
Matthew
The price is AED 340
AED 381 total
includes taxes & fees
5 Apr - 6 Apr
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, (720 reviews)
"Amazing location and staff!"
United States
Bobbi J.
The price is AED 404
AED 448 total
includes taxes & fees
23 Mar - 24 Mar
Hyatt Place Kent Narrows & Marina
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, (440 reviews)
"Very clean room, staff was very nice. "
United States
Byron
The price is AED 609
AED 770 total
includes taxes & fees
15 Mar - 16 Mar
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, (1,875 reviews)
"Staff were a pleasure. Room was beautiful. "
United States
Rachel
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, (247 reviews)
"Very friendly staff and easy check in."
United States
Kurt
The price is AED 404
AED 452 total
includes taxes & fees
22 Mar - 23 Mar
Hilton Garden Inn Bel Air
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
" Clean, comfortable, good location."
Michele Patricia 1-night trip
Posted 9 hours ago
Hilton Garden Inn Baltimore/White Marsh

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Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 41 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 Northern Chesapeake Bay.
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 WiFi, and free parking. Hampton Inn Baltimore/Glen Burnie: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Pendry Baltimore: Hotel with restaurant. Enjoy the bar, free WiFi, and rooftop terrace.
What is there to do in Chestertown?
In the area, you can visit Historical Society of Kent County Maryland, Betterton Beach, and Rock Hall Harbor, 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.