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Check prices for these dates

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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Our top choices for Chestertown Historic District hotels

A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A hotel room with a desk, two chairs, a flat-screen TV, and a painting on the wall.
A hotel room with a bed, a sofa, a dining table, and a small round table.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.3 km from Chestertown Historic District
United States
Roberta
₹9,318
₹10,343 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.
A living room with a fireplace, a television, and a stone accent wall.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.2 km from Chestertown Historic District
United States
Kate
₹6,834
₹7,586 total
includes taxes & fees
27 Oct - 28 Oct
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.
A two-story building with a brick facade, large windows, and a sloped roof.
A living room with a wooden cabinet, a television, a sofa, and a dining table.

3. Driftwood Inn

Driftwood Inn
1.6 km from Chestertown Historic District
United States
Kathy
₹6,028
₹6,691 total
includes taxes & fees
25 Oct - 26 Oct
Driftwood Inn
A boat deck with a white bench and a view of a calm lake and distant trees.
A buffet with various food items including fruits, pastries, and salads.
A sunflower field with a white barn and a large house in the background.
A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

4. Inn at Huntingfield Creek

Inn at Huntingfield Creek
17.8 km from Chestertown Historic District
United States
Christine
₹13,300
₹14,764 total
includes taxes & fees
16 Nov - 17 Nov
Inn at Huntingfield Creek
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 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.
A row of stationary bicycles with green frames and white seats, parked outdoors.

5. Haven Point Inn and Gallery

Haven Point Inn and Gallery
17.9 km from Chestertown Historic District
United States
Joe
₹12,687
₹14,082 total
includes taxes & fees
27 Oct - 28 Oct
Haven Point Inn and Gallery
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A campfire in a stone fire pit by a lakeside at sunset.
A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

6. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
13.3 km from Chestertown Historic District
United States
Steve allen
₹10,252
₹11,721 total
includes taxes & fees
22 Oct - 23 Oct
The Lodge at Great Oak Landing
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Compare popular hotels close to Chestertown Historic District

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
Comfort Inn & Suites Chestertown
8.6
Excellent
990 reviews
View
A hotel room with a sofa, two beds, a painting, and a lamp.
Red Roof Inn & Suites Chestertown
7.2
Good
511 reviews
View
A row of motel rooms with stone walls and red doors.
Driftwood Inn
5.4
183 reviews
View
A boat deck with a white bench and a view of a calm lake and distant trees.
Inn at Huntingfield Creek
10.0
Exceptional
74 reviews
View
A two-story house with a covered porch, a staircase, and a garden area.
Haven Point Inn and Gallery
9.6
Exceptional
16 reviews
View

Top Chestertown Historic District Hotel Reviews

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"The rooms very clean and accommodating. Definitely will stay there again when we travel through."
Frank 1-night trip
Posted less than an hour ago
Hampton Inn & Suites Edgewood/Aberdeen-South
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

10/10 Excellent
"Great hotel and lovely pool."
Sophia 1-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

8/10 Good
"Small room for 2 persons only one trash can Pillows were lumpy bumpy Mattress not great No iron./table Clean room had fridge microwave Breakfast is modest Good location Convenient"
andrew 1-night trip
Posted 2 hours ago
Quality Inn Grasonville near Kent Island
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"Everything was excellent with the room and staff. What I didn’t like is à la carte menu Other than that I was pleased with my stay"
Debra 2-night trip
Posted 20 hours ago
Hilton Garden Inn Baltimore/White Marsh
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

8/10 Good
"Good location, easy access to local restaurants. The staff is friendly and helpful. I would recommend staying here"
Terry Kyungho 2-night trip
Posted 1 day ago
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG

8/10 Good
"Good"
Tania 1-night trip
Posted 1 day ago
Holiday Inn Express White Marsh by IHG
WoodSpring Suites Baltimore White Marsh - Nottingham

WoodSpring Suites Baltimore White Marsh - Nottingham

8/10 Good
"WiFi was not working"
Diana 1-night trip
Posted 2 days ago
WoodSpring Suites Baltimore White Marsh - Nottingham
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"We were in town for a wedding. The hotel was close to the venue which is why we chose it. The staff was very friendly upon check in, the room was very clean, nice bathroom, comfortable bed and the view of the bay from our room was fabulous! The included breakfast was the standard breakfast items but very good!"
Beth 1-night trip
Posted 2 days ago
Best Western Kent Narrows Inn
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Wonderful staff! Had a problem getting into the bed because it was too high and I was too short. They were wonderful with accommodating my needs! They moved me to a new room and location!"
Katherine 2-night trip
Posted 2 days ago
The Inn at Chesapeake Bay Beach Club

Other attractions near Chestertown Historic District

Garfield Center for the Arts at the Prince Theater

6.8/10 (5 reviews)
You can make plans for a show at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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Historical Society of Kent County Maryland

7.4/10 (6 reviews)
You can spend an afternoon browsing the exhibits at Historical Society of Kent County Maryland during your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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Sumner Hall

You can spend time exploring the galleries in Sumner Hall during your travels in Chestertown. Experience the area's festivals and art scene.
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Chestertown Farmers Market

You can find the perfect gifts to bring home at Chestertown Farmers Market during your trip to Chestertown. Experience the area's festivals and art scene.
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River Arts Chestertown

7.4/10 (6 reviews)
Enjoy the student vibe when you visit River Arts Chestertown during your trip to Chestertown. Take in the festivals in this family-friendly area.
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Wilmer Park

8.2/10 (13 reviews)
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
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Kings Town Park

Kings Town Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.
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Larrabee Arts Center

Enjoy an outing to Larrabee Arts Center during your stay in Chestertown. Experience the area's festivals and art scene.
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Frequently asked questions

What's the area like around Chestertown Historic District?
Chestertown Historic District is located in Chestertown. Travellers like the surrounding area for its university setting. If you're looking for a convenient place to stay, take a look at the 17 hotels and other accommodation options you'll find within a mile.
What's the best place to stay close to Chestertown Historic District?
Quality Inn Grasonville near Kent Island is one of the top choices for your stay based on our traveller data, and this hotel offers free breakfast and free parking. You'll find it 18.6 mi (29.9 km) from Chestertown Historic District. Other good options around the area include Holiday Inn Express Annapolis East-Kent Island by IHG and Hilton Garden Inn Kent Island Marina.
How many hotels should I expect to find near Chestertown Historic District?
Expedia has 17 hotels and other accommodation options within a mile from Chestertown Historic District.
If I need to cancel the hotel reservation for my stay near Chestertown Historic District, will I receive a refund?
Yes, most hotel room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within a 24-hour period of your booking. Plug in your dates, click on "Search", then you can filter by "fully refundable" to view the best options available near Chestertown Historic District.