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 NT$3,422
NT$3,912 total
includes taxes & fees
Mar 16 - Mar 17
The Lodge at Great Oak Landing
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
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)
"Clean room, I enjoy staying here every time I'm in the area"
United States
Peter
The price is NT$3,327
NT$3,692 total
includes taxes & fees
Mar 18 - Mar 19
Holiday Inn Express Annapolis East-Kent Island by IHG
Restaurant

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (226 reviews)
"Had a very pleasant check in with this hotel. Many restaurants are within a mile of the hotel. Very close to I-95. "
United States
Dennis
The price is NT$2,935
NT$3,287 total
includes taxes & fees
Apr 5 - Apr 6
Courtyard Aberdeen at Ripken Stadium
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 NT$3,611
NT$4,008 total
includes taxes & fees
Mar 15 - Mar 16
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)
"Clean room.breakfast was great.Staff.was helpful."
United States
Susan
The price is NT$3,014
NT$3,345 total
includes taxes & fees
Mar 30 - Mar 31
Hampton Inn Middletown
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, (439 reviews)
"Amazing rooms and service!"
United States
Alicia
The price is NT$5,255
NT$6,640 total
includes taxes & fees
Mar 15 - Mar 16
The Inn at Chesapeake Bay Beach Club
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (719 reviews)
"Amazing location and staff!"
United States
Bobbi J.
The price is NT$3,485
NT$3,868 total
includes taxes & fees
Mar 16 - Mar 17
Hyatt Place Kent Narrows & Marina
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, (246 reviews)
"Very friendly staff and easy check in."
United States
Kurt
The price is NT$3,533
NT$3,957 total
includes taxes & fees
Mar 26 - Mar 27
Hilton Garden Inn Bel Air
Lobby

Residence Inn Aberdeen at Ripken Stadium

Residence Inn Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
9.2 out of 10, Wonderful, (110 reviews)
"This is always a great place to stay in the winter time when we visit family in the area. Only complaint was the smoke alarm going off at 10pm in the room and in the hallway, but it quickly stopped. Would recommend a stay."
United States
TERRY
The price is NT$3,474
NT$3,891 total
includes taxes & fees
Mar 31 - Apr 1
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

Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

2/10 Terrible
"STRAIGHT TO THE POINT! Beyond pissed my first room 209 blood on the curtains and floor. Old vibe room and smoked out. furniture carpet towels OLD and DIRTY. The public dining area was dirty. I was highly disgusted and really want my money back"
Traci 2-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Baltimore North, MD

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. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Hotel with restaurant. Enjoy the 2 bars, free WiFi, and seasonal outdoor pool. Historic Inns of Annapolis: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Pendry Baltimore: Hotel with restaurant. Enjoy the bar, free WiFi, and rooftop terrace. Hampton Inn Baltimore/Glen Burnie: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi.
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.

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