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Chestertown Bar Hotel

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Check availability on Chestertown Bar Hotel

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

Our top choices for Chestertown hotels with a bar

Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (558 reviews)
"A beautiful and romantic Victorian B&B with friendly staff and delicious breakfast. We absolutely loved our stay and would go back again if we were ever in the area."
United States
Shannon
The price is HK$1,133
HK$1,269 total
includes taxes & fees
6 Jul - 7 Jul
Vandiver Inn
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,867 reviews)
"Great hotel..will definitely be back"
United States
Randy
The price is HK$707
HK$1,074 total
includes taxes & fees
12 Jul - 13 Jul
Historic Inns of Annapolis
Reception

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (663 reviews)
"Friendly staff and clean room."
United States
Vivian karla
The price is HK$887
HK$993 total
includes taxes & fees
3 Aug - 4 Aug
Hilton Garden Inn Aberdeen
Restaurant

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (228 reviews)
"Room were very clean, staff were excellent and friendly and helpful!"
United States
Matthew
The price is HK$660
HK$739 total
includes taxes & fees
2 Aug - 3 Aug
Courtyard Aberdeen at Ripken Stadium
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (906 reviews)
"I definitely will be booking my stay again in middle town."
United States
Taylor
The price is HK$1,003
HK$1,113 total
includes taxes & fees
3 Aug - 4 Aug
Hampton Inn Middletown
Exterior

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.6 out of 10, Exceptional, (5 reviews)
"Room was very clean and the owner was very helpful will definitely stay there again"
United States
John
The price is HK$1,094
HK$1,214 total
includes taxes & fees
7 Jul - 8 Jul
Haven Point Inn and Gallery
Bar (on property)

Travelodge by Wyndham Aberdeen

Travelodge by Wyndham Aberdeen
2.0 star property
Aberdeen
6.4 out of 10, (573 reviews)
"Easy access to all nearby businesses."
United States
Grady
The price is HK$522
HK$585 total
includes taxes & fees
28 Jul - 29 Jul
Travelodge by Wyndham Aberdeen
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, (468 reviews)
"Wonderful stay! Everything was amazing..,the staff, rooms, Knoxie’s Table, the spa! Couldn’t have asked for a better stay. I’ll definitely return."
United States
Damika
The price is HK$1,769
HK$2,164 total
includes taxes & fees
6 Jul - 7 Jul
The Inn at Chesapeake Bay Beach Club
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, (283 reviews)
"Nice room, good space, clean, nice location good breakfast. I’d definitely stay there again."
United States
Paulo
The price is HK$958
HK$1,073 total
includes taxes & fees
3 Aug - 4 Aug
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
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (115 reviews)
"Rooms well stocked clean roomy enjoyed stay will use again"
United States
Dorthy
The price is HK$860
HK$963 total
includes taxes & fees
2 Aug - 3 Aug
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.
View all properties

Top Chestertown Hotel Reviews

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

8/10 Good
"The staff was very nice and welcoming The room was little hot good thing i are able to adjust the temperature Pool was really nice my kids enjoy Didn’t do breakfast but it look really good we was already heading out tho"
Shermekqua 1-night trip
Posted 2 hours ago
Hilton Garden Inn Baltimore/White Marsh

Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 44 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 Chestertown Historic District and Rolphs Wharf Marina.
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. The Lodge at Great Oak Landing: Hotel with restaurant. Enjoy the 2 bars, free WiFi and seasonal outdoor pool. Red Roof Inn & Suites Chestertown: Hotel with restaurant. Enjoy the bar, free breakfast and free WiFi. Historic Inns of Annapolis: 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 Chestertown Historic District, Rolphs Wharf Marina and The Mainstay, 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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