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Check availability on Chestertown Hotels with a Bar

Top 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
8.0 out of 10, Very good, (75)
"Very nice rooms, "
United States
Stephania
The price is 2.608.947 ₫
2.982.809 ₫ total
includes taxes & fees
20 Nov - 21 Nov
The Lodge at Great Oak Landing
Reception
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
8.8 out of 10, Excellent, (854)
"Enjoyed the amenities and great location for shops nearby "
United States
Erica
The price is 2.719.630 ₫
3.018.790 ₫ total
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn Middletown
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, (1000)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
The price is 2.681.682 ₫
2.976.667 ₫ total
includes taxes & fees
25 Nov - 26 Nov
Hilton Garden Inn Kent Island Marina
Lobby lounge
Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium

3.0 star property
Aberdeen
8.6 out of 10, Excellent, (214)
"Excellent place to stay. A wonderful maid helped us. Room great and food excellent evening and morning."
United States
Bartley
The price is 2.217.605 ₫
2.483.717 ₫ total
includes taxes & fees
4 Dec - 5 Dec
Courtyard Aberdeen at Ripken Stadium
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, (924)
"The hotel was nice and clean and the staff was always polite and helpful. "
United States
William
The price is 2.714.359 ₫
3.012.939 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Reception
Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air

3.0 star property
Bel Air
9.2 out of 10, Wonderful, (222)
"Friendly staff, clean hotel "
United States
Kelly
The price is 2.511.281 ₫
2.812.635 ₫ total
includes taxes & fees
3 Dec - 4 Dec
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, (106)
"The view from our room of the Cal Ripkin complex was amazing. "
United States
Christopher
The price is 2.665.606 ₫
2.985.480 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Residence Inn Aberdeen at Ripken Stadium
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio
Vandiver Inn

Vandiver Inn

3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (529)
"Lovely inn & receptionist was wonderful. "
United States
Deborah
Vandiver Inn
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (655)
"My favorite hotel "
United States
Jen
The price is 4.190.127 ₫
4.651.041 ₫ total
includes taxes & fees
20 Nov - 21 Nov
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, (427)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is 4.844.883 ₫
6.048.240 ₫ total
includes taxes & fees
1 Dec - 2 Dec
The Inn at Chesapeake Bay Beach Club
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

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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 Chestertown Historic District.
What is there to do in Chestertown?
In the area, you can visit Historical Society of Kent County Maryland, Chestertown Historic District and Rolphs Wharf Marina, 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.