Find Hotels with Bars in Chestertown, MD

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Check availability on Chestertown Hotels with Bars

Our top choices for Chestertown hotels with a bar

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (871 reviews)
"Amazing stay"
United States
Katiana
The price is NT$3,007
NT$3,338 total
includes taxes & fees
Jan 28 - Jan 29
Hampton Inn Middletown

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, (954 reviews)
"Lovely location"
United States
Cheryl
The price is NT$2,750
NT$3,053 total
includes taxes & fees
Feb 16 - Feb 17
Holiday Inn Express Annapolis East-Kent Island by IHG

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (636 reviews)
"High quality pillows Comfortable bed Clean room Kuerig Big room Strong WiFi Clean shower Good shampoo Excellent towels Plenty of drawers and closet space Comfy chair Great desk space"
United States
John
The price is NT$2,750
NT$3,081 total
includes taxes & fees
Feb 22 - Feb 23
Hilton Garden Inn Aberdeen

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (221 reviews)
"Had a very pleasant check in with this hotel. Many restaurants are within a mile of the hotel. Very close to I-95. "
United States
Dennis
The price is NT$2,660
NT$2,979 total
includes taxes & fees
Feb 22 - Feb 23
Courtyard Aberdeen at Ripken Stadium

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (704 reviews)
"Room was spotless, staff was exceptionally friendly."
United States
Maxwell
The price is NT$4,267
NT$4,737 total
includes taxes & fees
Jan 28 - Jan 29
Hyatt Place Kent Narrows & Marina

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, (434 reviews)
"Amazing rooms and service!"
United States
Alicia
The price is NT$4,930
NT$6,276 total
includes taxes & fees
Feb 1 - Feb 2
The Inn at Chesapeake Bay Beach Club

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (240 reviews)
"Very friendly staff and easy check in."
United States
Kurt
The price is NT$3,088
NT$3,458 total
includes taxes & fees
Jan 30 - Jan 31
Hilton Garden Inn Bel Air

Residence Inn Aberdeen at Ripken Stadium

Residence Inn Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
9.2 out of 10, Wonderful, (108 reviews)
"This is always a great place to stay in the winter time when we visit family in the area. Only complaint was the smoke alarm going off at 10pm in the room and in the hallway, but it quickly stopped. Would recommend a stay."
United States
TERRY
The price is NT$3,201
NT$3,585 total
includes taxes & fees
Feb 20 - Feb 21
Residence Inn Aberdeen at Ripken Stadium

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, (748 reviews)
"Definitely was a great stay !"
United States
Shawn
The price is NT$2,244
NT$2,514 total
includes taxes & fees
Jan 25 - Jan 26
Holiday Inn Belcamp - Aberdeen Area by IHG

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (535 reviews)
"a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back"
United States
Dieter
Vandiver Inn
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.

Top Chestertown Hotel Reviews

Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 40 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 Chestertown Historic District and Northern Chesapeake Bay.
What are the best hotels with bars in Chestertown?
Here are some favorite hotels with bars in and around Chestertown: Comfort Inn & Suites Chestertown: Hotel with restaurant. Enjoy the 2 bars, free WiFi, and seasonal outdoor pool. Pendry Baltimore: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Enjoy the bar, free WiFi, and room service. Hilton Garden Inn Baltimore/White Marsh: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Historic Inns of Annapolis: Hotel with restaurant. Enjoy the bar, free WiFi, and rooftop terrace.
What is there to do in Chestertown?
In the area, you can visit Chestertown Historic District, Betterton Beach, and Rock Hall Harbor, 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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