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

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very Good, (82 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again "
United States
Nicola
The price is NT$4,181
NT$4,781 total
includes taxes & fees
May 28 - May 29
The Lodge at Great Oak Landing

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (545 reviews)
"A beautiful and romantic Victorian B&B with friendly staff and delicious breakfast. We absolutely loved our stay and would go back again if we were ever in the area."
United States
Shannon
The price is NT$4,567
NT$5,115 total
includes taxes & fees
Jun 15 - Jun 16
Vandiver Inn

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
10.0 out of 10, Exceptional, (1 review)
"Room was very clean and the owner was very helpful will definitely stay there again"
United States
John
The price is NT$4,899
NT$5,438 total
includes taxes & fees
May 27 - May 28
Haven Point Inn and Gallery

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (653 reviews)
"Overall, everything was great. I just had to go down to get some towels. I would recommend this place to everyone."
United States
Venus
The price is NT$3,343
NT$3,744 total
includes taxes & fees
Jun 7 - Jun 8
Hilton Garden Inn Aberdeen

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (902 reviews)
"Great place to stay"
United States
Ken
The price is NT$4,175
NT$4,634 total
includes taxes & fees
May 28 - May 29
Hampton Inn Middletown

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (228 reviews)
"Room were very clean, staff were excellent and friendly and helpful!"
United States
Matthew
The price is NT$3,197
NT$3,580 total
includes taxes & fees
May 27 - May 28
Courtyard Aberdeen at Ripken Stadium

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,837 reviews)
"Great location"
United States
Stephanie
The price is NT$3,657
NT$5,250 total
includes taxes & fees
May 31 - Jun 1
Historic Inns of Annapolis

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (275 reviews)
"Nice room, good space, clean, nice location good breakfast. I’d definitely stay there again."
United States
Paulo
The price is NT$4,030
NT$4,513 total
includes taxes & fees
Jun 7 - Jun 8
Hilton Garden Inn Bel Air

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (763 reviews)
"Great Stay!!"
United States
Richard
The price is NT$5,847
NT$6,490 total
includes taxes & fees
May 26 - May 27
Hyatt Place Kent Narrows & Marina

Residence Inn Aberdeen at Ripken Stadium

Residence Inn Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (114 reviews)
"The staff are exceptional "
United States
Gina
The price is NT$3,465
NT$3,881 total
includes taxes & fees
Jun 14 - Jun 15
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.

Top Chestertown Hotel Reviews

Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 44 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 Rolphs Wharf Marina 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: 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 bar, free breakfast, and free WiFi. Historic Inns of Annapolis: Hotel with restaurant. Enjoy the 2 bars, free WiFi, and seasonal outdoor pool. Hampton Inn Baltimore/Glen Burnie: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking.
What is there to do in Chestertown?
In the area, you can visit Rolphs Wharf Marina, 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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