Find Hotels with Bars in Chestertown, MD

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Check availability on Chestertown Hotels with Bars

Top Chestertown Hotels with Bars

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, (76)
"Very nice rooms, "
United States
Stephania
The price is NT$3,092
NT$3,535 total
includes taxes & fees
Nov 25 - Nov 26
The Lodge at Great Oak Landing
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, (1001)
"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 NT$3,178
NT$3,527 total
includes taxes & fees
Nov 30 - Dec 1
Hilton Garden Inn Kent Island Marina
Reception
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
8.8 out of 10, Excellent, (855)
"Enjoyed the amenities and great location for shops nearby "
United States
Erica
The price is NT$3,223
NT$3,577 total
includes taxes & fees
Dec 1 - Dec 2
Hampton Inn Middletown
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 NT$2,628
NT$2,943 total
includes taxes & fees
Dec 7 - Dec 8
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)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is NT$2,974
NT$3,302 total
includes taxes & fees
Dec 14 - Dec 15
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 NT$2,973
NT$3,330 total
includes taxes & fees
Dec 3 - Dec 4
Hilton Garden Inn Bel Air
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 NT$5,741
NT$7,167 total
includes taxes & fees
Dec 1 - Dec 2
The Inn at Chesapeake Bay Beach Club
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1900)
"Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!"
United States
Christine
Historic Inns of Annapolis
Exterior
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, (735)
"Room was very nice and clean, the pool was amazing, my grandchildren loved the stay very much , ill definitely use holiday inn again "
United States
Anna
The price is NT$2,473
NT$2,770 total
includes taxes & fees
Nov 25 - Nov 26
Holiday Inn Belcamp - Aberdeen Area by IHG
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 NT$3,160
NT$3,540 total
includes taxes & fees
Dec 21 - Dec 22
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

The Inn at Henderson's Wharf, an Ascend Collection Hotel

The Inn at Henderson's Wharf, an Ascend Collection Hotel

10/10 Excellent
"Never have a bad stay here. Rooms are always clean, staff is always friendly. Coffee machine is wonderful. Happy Hour was great each night. This is a must stay if in Fells Point!"
Kyle 3-night trip
Posted 2 days ago
The Inn at Henderson's Wharf, an Ascend Collection Hotel

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Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 39 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 Chestertown Historic District.
What are the best hotels with bars in Chestertown?
Here are some favorite hotels with bars in and around Chestertown: Comfort Inn & Suites Chestertown: Lodge with restaurant. Enjoy the 3 bars, free WiFi, and free parking. Red Roof 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. 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.
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 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.