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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
7.8 out of 10, Good, (72)
"For the price off season the room should have had better amenities "
United States
Daniel
The price is AED 486
AED 556 total
includes taxes & fees
27 Oct - 28 Oct
The Lodge at Great Oak Landing
Reception
Hampton Inn Middletown
Hampton Inn Middletown
2.5 star property
8.8 out of 10, Excellent, (844)
"Enjoyed the amenities and great location for shops nearby "
United States
Erica
The price is AED 383
AED 425 total
includes taxes & fees
19 Nov - 20 Nov
Hampton Inn Middletown
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
9.2 out of 10, Wonderful, (907)
"Nice Holiday Inn Express with great water views."
United States
Michael
The price is AED 408
AED 453 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior
Hilton Garden Inn Baltimore/White Marsh
Hilton Garden Inn Baltimore/White Marsh
3.0 star property
7.8 out of 10, Good, (1003)
"Great stay"
United States
Ronald
The price is AED 337
AED 389 total
includes taxes & fees
23 Nov - 24 Nov
Hilton Garden Inn Baltimore/White Marsh
Lobby lounge
Courtyard Aberdeen at Ripken Stadium
Courtyard Aberdeen at Ripken Stadium
3.0 star property
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 AED 309
AED 346 total
includes taxes & fees
20 Nov - 21 Nov
Courtyard Aberdeen at Ripken Stadium
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio
Vandiver Inn
Vandiver Inn
3.5 star property
9.4 out of 10, Exceptional, (525)
"Vandiver Inn was wonderful. Incredibly hospitable and welcoming staff. Lovely room and common areas. Delicious breakfast. I will definitely be visiting again."
United States
Barbara Lindsay
Vandiver Inn
Terrace/patio
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
9.4 out of 10, Exceptional, (642)
"Nice location and restaurants galore in area. "
United States
David
The price is AED 547
AED 607 total
includes taxes & fees
2 Nov - 3 Nov
Hyatt Place Kent Narrows & Marina
Reception
Hilton Garden Inn Bel Air
Hilton Garden Inn Bel Air
3.0 star property
9.2 out of 10, Wonderful, (217)
"Friendly staff, clean hotel "
United States
Kelly
The price is AED 376
AED 422 total
includes taxes & fees
23 Nov - 24 Nov
Hilton Garden Inn Bel Air
Terrace/patio
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1854)
"Great location "
United States
Karyl
Historic Inns of Annapolis
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
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 AED 434
AED 486 total
includes taxes & fees
17 Nov - 18 Nov
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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"On arrival we met Catalina on reception. An extremely pleasant and helpful girl. After that our stay was very comfortable."
Christopher 1-night trip
Posted 2 days ago
Hilton Garden Inn Baltimore/White Marsh

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Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 38 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 Rolphs Wharf Marina.
What are the best hotels with bars in Chestertown?
Here are some favorite hotels with bars in and around Chestertown: Red Roof Inn & Suites Chestertown: Lodge with restaurant. Enjoy the 3 bars, free WiFi, and free parking. 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. 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, Rolphs Wharf Marina, and The Mainstay, then find a cozy spot for a nightcap. Other places to see include Chesapeake Bay and Garfield Center for the Arts at the Prince Theater.
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.