Chestertown Bar Hotel

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Our top choices for Chestertown hotels with a bar

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, (947)
"It was very comfortable and clean"
United States
Maria
The price is HK$677
HK$752 total
includes taxes & fees
19 Jan - 20 Jan
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (870)
"Amazing stay"
United States
Katiana
The price is HK$741
HK$822 total
includes taxes & fees
14 Jan - 15 Jan
Hampton Inn Middletown
Reception
Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (635)
"High quality pillows Comfortable bed Clean room Kuerig Big room Strong WiFi Clean shower Good shampoo Excellent towels Plenty of drawers and closet space Comfy chair Great desk space"
United States
John
The price is HK$612
HK$685 total
includes taxes & fees
30 Jan - 31 Jan
Hilton Garden Inn Aberdeen
Bar (on property)
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, (237)
"Kind staff, very clean. Lovely stay!"
Canada
Michelle
The price is HK$760
HK$851 total
includes taxes & fees
23 Jan - 24 Jan
Hilton Garden Inn Bel Air
Restaurant
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, (219)
"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 HK$655
HK$734 total
includes taxes & fees
25 Jan - 26 Jan
Courtyard Aberdeen at Ripken Stadium
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, (695)
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is HK$894
HK$993 total
includes taxes & fees
19 Jan - 20 Jan
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, (433)
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is HK$1,214
HK$1,546 total
includes taxes & fees
1 Feb - 2 Feb
The Inn at Chesapeake Bay Beach Club
Exterior
Holiday Inn Belcamp - Aberdeen Area by IHG

Holiday Inn Belcamp - Aberdeen Area by IHG

Holiday Inn Belcamp - Aberdeen Area by IHG
3.0 star property
Belcamp
8.4 out of 10, Very good, (744)
"Definitely was a great stay !"
United States
Shawn
The price is HK$592
HK$663 total
includes taxes & fees
11 Jan - 12 Jan
Holiday Inn Belcamp - Aberdeen Area by IHG
Exterior detail
Vandiver Inn

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (533)
"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
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
9.2 out of 10, Wonderful, (108)
"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 HK$788
HK$882 total
includes taxes & fees
29 Jan - 30 Jan
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

Home2 Suites by Hilton Baltimore/White Marsh

Home2 Suites by Hilton Baltimore/White Marsh

10/10 Excellent
"The staff was very courteous, the rooms are comfortable, all appliances and kitchenware were in working condition. The rooms were clean. An extended thank you to Ahmed for his professional service and hospitality. We will definitely return."
Evelyn 2-night trip
Posted 4 days ago
Home2 Suites by Hilton Baltimore/White Marsh

Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 39 hotels and other accommodation options to choose from, and likely many will have a bar where you can enjoy drink after exploring the city. 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?
Below are some of top hotels with bars in and around Chestertown: Comfort Inn & Suites Chestertown: Enjoy the bar, free WiFi and room service. Red Roof Inn & Suites Chestertown: 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 breakfast and free WiFi. Hilton Garden Inn Baltimore/White Marsh: 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 cosy 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 rainfall averages and temperatures can help you determine the best time for bar-hopping. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
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) away from the heart of the city. 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, you may want to rent a car for your trip.

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