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Chestertown Bar Hotel

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Top Chestertown Bar Hotel

Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
10.0 out of 10, Exceptional, (1)
"We recently had the pleasure of staying at the Inn at Haven Harbour, specifically at their south location, and can't say enough good things about our experience! From the moment we arrived, we were captivated by the immaculate property and stunning surroundings. The views of the water were breathtaking, and having access to a private beach made our stay feel even more special. The amenities were top-notch, with a pool available for those who prefer a swim to the beach. The staff were incredibly...
The price is HK$1,644
HK$1,982 total
includes taxes & fees
5 Aug - 6 Aug
Inn at Haven Harbour
Vandiver Inn
Terrace/patio

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (507)
"Staff was very friendly. We had a very relaxing stay. "
Vandiver Inn
The Lodge at Great Oak Landing
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (57)
"Great place to get some quiet rest by the water"
The price is HK$1,039
HK$1,153 total
includes taxes & fees
5 Aug - 6 Aug
The Lodge at Great Oak Landing
Hampton Inn Middletown
Reception

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (818)
"Front desk service was exceptional!!"
The price is HK$861
HK$955 total
includes taxes & fees
11 Aug - 12 Aug
Hampton Inn Middletown
SpringHill Suites Baltimore White Marsh/Middle River
Desk, laptop workspace, blackout curtains, iron/ironing board

SpringHill Suites Baltimore White Marsh/Middle River

2.5 star property
9.0 out of 10, Wonderful, (717)
"Great stay"
The price is HK$962
HK$1,111 total
includes taxes & fees
10 Aug - 11 Aug
SpringHill Suites Baltimore White Marsh/Middle River
The Inn at Chesapeake Bay Beach Club
Front of property – evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (404)
"Staff was very polite and friendly. "
The price is HK$1,609
HK$1,986 total
includes taxes & fees
24 Aug - 25 Aug
The Inn at Chesapeake Bay Beach Club
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (603)
"Great place to stay. "
The price is HK$1,209
HK$1,342 total
includes taxes & fees
25 Aug - 26 Aug
Hyatt Place Kent Narrows & Marina
Hilton Garden Inn Bel Air
Reception

Hilton Garden Inn Bel Air

3.0 star property
9.4 out of 10, Exceptional, (204)
"The property was nice. The lady who checked me in was not friendly. A little rude. But overall it was a nice place to stay. "
The price is HK$994
HK$1,113 total
includes taxes & fees
10 Aug - 11 Aug
Hilton Garden Inn Bel Air
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (975)
"Friendly staff, nice environment"
The price is HK$1,209
HK$1,343 total
includes taxes & fees
10 Aug - 11 Aug
Hilton Garden Inn Kent Island Marina
Holiday Inn Belcamp - Aberdeen Area by IHG
Exterior

Holiday Inn Belcamp - Aberdeen Area by IHG

3.0 star property
8.4 out of 10, Very good, (708)
"Very clean! "
The price is HK$824
HK$923 total
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn Belcamp - Aberdeen Area by IHG
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

The Inn at Henderson's Wharf, Ascend Hotel Collection

The Inn at Henderson's Wharf, Ascend Hotel Collection

10/10 Excellent
"My husband was having surgery nearby and I found this hotel to be a lovely little respite to come home to each evening. I treated myself to a waterfront room which could not have been more peaceful and serene. Perfect simple breakfast, great area. "
Wendy 2-night trip
Posted 2 days ago
The Inn at Henderson's Wharf, Ascend Hotel Collection

Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 44 hotels and other accommodation options to choose from, and likely many will have a bar where you can enjoy drink after exploring the city. 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?
Below are some of top 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 WiFi and rooftop terrace. Sagamore 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 cosy spot for a nightcap. Other places to see include Garfield Center for the Arts at the Prince Theater and Chestertown Historic District.
When is the best time to visit Chestertown?
Visiting local bars in Chestertown is better when you know what the weather holds. These rainfall averages and temperatures can help you determine the best time for bar-hopping. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
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) away from the heart of the city. 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, you may want to rent a car for your trip.