Find Hotels with Bars in Chestertown, MD

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Top Chestertown Hotels with Bars

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
$113 nightly
The price is $126
Nov 27 - Nov 28
Total with taxes and fees
The Lodge at Great Oak Landing

Hampton Inn Middletown

2.5 star property
Middletown
8.8 out of 10, Excellent, (856)
"Enjoyed the amenities and great location for shops nearby "
United States
Erica
$103 nightly
The price is $115
Dec 3 - Dec 4
Total with taxes and fees
Hampton Inn Middletown

Courtyard Aberdeen at Ripken Stadium

3.0 star property
Aberdeen
8.6 out of 10, Excellent, (215)
"Excellent place to stay. A wonderful maid helped us. Room great and food excellent evening and morning."
United States
Bartley
$84 nightly
The price is $94
Dec 14 - Dec 15
Total with taxes and fees
Courtyard Aberdeen at Ripken Stadium

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
9.2 out of 10, Wonderful, (925)
"nice, clean, up to date, budget friendly hotel"
United States
mike
$79 nightly
The price is $88
Dec 1 - Dec 2
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1003)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
$119 nightly
The price is $132
Dec 3 - Dec 4
Total with taxes and fees
Hilton Garden Inn Kent Island Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (663)
"My favorite hotel "
United States
Jen
$116 nightly
The price is $129
Nov 30 - Dec 1
Total with taxes and fees
Hyatt Place Kent Narrows & Marina

The Inn at Chesapeake Bay Beach Club

4.0 star property
Stevensville
9.4 out of 10, Exceptional, (428)
"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
$207 nightly
The price is $230
Dec 1 - Dec 2
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club

Hilton Garden Inn Bel Air

3.0 star property
Bel Air
9.2 out of 10, Wonderful, (225)
"Friendly staff, clean hotel "
United States
Kelly
$95 nightly
The price is $107
Dec 7 - Dec 8
Total with taxes and fees
Hilton Garden Inn Bel Air

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1905)
"Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!"
United States
Christine
$154 nightly
The price is $175
Dec 3 - Dec 4
Total with taxes and fees
Historic Inns of Annapolis

Vandiver Inn

3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (529)
"Lovely inn & receptionist was wonderful. "
United States
Deborah
$145 nightly
The price is $163
Dec 3 - Dec 4
Total with taxes and fees
Vandiver Inn
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Top Chestertown Hotel Reviews

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 breakfast, and free WiFi. 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 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.

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