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 SAR 372
SAR 425 total
includes taxes & fees
7 Dec - 8 Dec
The Lodge at Great Oak Landing
Reception
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
8.8 out of 10, Excellent, (857)
"Enjoyed the amenities and great location for shops nearby "
United States
Erica
The price is SAR 387
SAR 430 total
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn Middletown
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
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1002)
"Room was great! In room tub was a bit smaller than I was expecting but still quite adequate! View from room was very nice."
United States
Madeline
The price is SAR 387
SAR 430 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Kent Island Marina
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, (930)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is SAR 296
SAR 329 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.6 out of 10, Exceptional, (671)
"Great view, good ambiance all around"
United States
Dianne
The price is SAR 436
SAR 484 total
includes taxes & fees
7 Dec - 8 Dec
Hyatt Place Kent Narrows & Marina
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 SAR 380
SAR 425 total
includes taxes & fees
28 Dec - 29 Dec
Residence Inn Aberdeen at Ripken Stadium
Lobby lounge
Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium

3.0 star property
Aberdeen
8.6 out of 10, Excellent, (216)
"We reserved 4 rooms, and arrived around noon. We didn't think, with early arrival, that our rooms would be ready, but they were! The staff was extremely accommodating and friendly. Our rooms were immaculate, beds comfy. It was a great stay for visiting family in the area. "
United States
Stephen
The price is SAR 316
SAR 354 total
includes taxes & fees
21 Dec - 22 Dec
Courtyard Aberdeen at Ripken Stadium
Bar (on property)
Travelodge by Wyndham Aberdeen

Travelodge by Wyndham Aberdeen

2.0 star property
Aberdeen
6.4 out of 10, (534)
"The Great place to stay "
United States
Hector
The price is SAR 175
SAR 196 total
includes taxes & fees
14 Dec - 15 Dec
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, (429)
"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 SAR 690
SAR 861 total
includes taxes & fees
8 Dec - 9 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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"Amazing "
Breonah 2-night trip
Posted 5 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 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: Hotel with restaurant. Enjoy the 2 bars, free WiFi, and seasonal outdoor pool. The Lodge at Great Oak Landing: Enjoy the bar, free WiFi, and room service. Pendry Baltimore: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: 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 Crumpton Auction and Northern 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.