An aerial view of a town with a river, buildings, and surrounding greenery.

Find Hotels with Bars in Chestertown, MD

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Check availability on Chestertown Hotels with Bars

Tonight
Oct 9 - Oct 10
Tomorrow
Oct 10 - Oct 11
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Chestertown hotels with a bar

A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.
A campfire in a stone fire pit by a lakeside at sunset.

1. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
United States
Sandra
NT$3,449
NT$3,944 total
includes taxes & fees
Oct 11 - Oct 12
The Lodge at Great Oak Landing
A two-story house with a covered porch, a staircase, and a garden area.
A bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.
A garden with a lawn and a table with chairs under a canopy.
A dining room with a long wooden table set for six, surrounded by chairs. There are framed pictures on the walls, a window with a view of trees, and a sofa in the background.

2. Haven Point Inn and Gallery

Haven Point Inn and Gallery
Rock Hall
United States
Joe
NT$4,269
NT$4,738 total
includes taxes & fees
Oct 13 - Oct 14
Haven Point Inn and Gallery
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.
A hotel room with two beds, a bathroom, and a seating area.
An outdoor patio with brick walls, green chairs, and a fire pit.
A hotel with a modern facade, a covered entrance, and a red car parked outside.

3. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
United States
Juanita
NT$3,421
NT$3,951 total
includes taxes & fees
Oct 15 - Oct 16
SpringHill Suites Baltimore White Marsh/Middle River
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
An outdoor event area with round tables and a view of the water.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

4. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
NT$4,855
NT$5,389 total
includes taxes & fees
Oct 18 - Oct 19
Hyatt Place Kent Narrows & Marina
A patio with outdoor seating, overlooking a marina with boats.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
An indoor swimming pool with clear views of boats and water.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

5. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
Charles
NT$4,426
NT$4,913 total
includes taxes & fees
Oct 19 - Oct 20
Hilton Garden Inn Kent Island Marina
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.
A modern coffee shop interior with a counter, shelves stocked with snacks, and a refrigerated display.
A modern hotel with a stone facade, a clear entrance canopy, and a prominent Hilton Inn sign.
A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.

6. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
United States
Jaccilynne
NT$3,502
NT$3,922 total
includes taxes & fees
Nov 2 - Nov 3
Hilton Garden Inn Bel Air
A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.
A formal dining room with a long table, chairs, a chandelier, and a fireplace.
A cozy living room with a sofa, armchair, and a fireplace.
A traditional house with a covered porch, white picket fence, and lush greenery.

7. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Mary
NT$5,583
NT$6,253 total
includes taxes & fees
Oct 12 - Oct 13
Vandiver Inn
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

8. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United States
scott
NT$6,516
NT$8,045 total
includes taxes & fees
Nov 2 - Nov 3
The Inn at Chesapeake Bay Beach Club
A hotel lobby with a reception desk, a coffee station, and a view of the garden through the window.
A buffet setup with food and drinks, a fireplace, and a menu sign.
A spacious lobby with a fireplace, comfortable seating, and a large television screen.
A hotel lobby with a large entrance, multiple hanging pendant lights, and potted plants.

9. Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
Aberdeen
United States
Philip
NT$3,117
NT$3,491 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Aberdeen
A hotel room with a kitchenette, a desk, a chair, a sofa, and a bathroom visible through an open door.
A gym with treadmills, dumbbells, and exercise equipment.
A hotel room with a kitchenette, a sofa, a coffee table, and a patterned rug.
A buffet setup with multiple self-service food dispensers.

10. Holiday Inn Belcamp - Aberdeen Area by IHG

Holiday Inn Belcamp - Aberdeen Area by IHG
Belcamp
United States
Jenny
NT$2,651
NT$2,969 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Belcamp - Aberdeen Area by IHG
View all properties

Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"A nice place to stay"
Christian 1-night trip
Posted 1 hour ago
Best Western Plus Hotel & Conference Center
Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Beautiful historic hotel. They have done a wonderful job maintaining the property. Everyone we met on our one night stay was very nice, helpful. We loved the area."
Tina 1-night trip
Posted 2 hours ago
Historic Inns of Annapolis

Frequently asked questions

Searching for hotels with bars in Chestertown?
Chestertown features 45 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: Red Roof Inn & Suites Chestertown: Lodge with 2 restaurants. Enjoy the 2 bars, free WiFi, and free parking. The Lodge at Great Oak Landing: Enjoy the bar, free WiFi, and room service. Comfort Inn & Suites Chestertown: 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 rooftop terrace.
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 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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