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Hotels near Chestertown Historic District

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Check prices for these dates

Tonight
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 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 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.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.3 km from Chestertown Historic District
United States
Roberta
RM402
RM446 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 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.
A living room with a fireplace, a television, and a stone accent wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.2 km from Chestertown Historic District
United States
Kate
RM294
RM326 total
includes taxes & fees
29 Oct - 30 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 living room with two patterned armchairs, a wooden coffee table, and a standing fan.
A two-story building with a brick facade, large windows, and a sloped roof.

3. Driftwood Inn

Driftwood Inn
1.6 km from Chestertown Historic District
United States
Kathy
RM259
RM288 total
includes taxes & fees
27 Oct - 28 Oct
Driftwood Inn
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.
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 campfire in a stone fire pit by a lakeside at sunset.

4. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
13.3 km from Chestertown Historic District
United States
Steve allen
RM441
RM504 total
includes taxes & fees
25 Oct - 26 Oct
The Lodge at Great Oak Landing
A two-story house with a covered porch, a staircase, and a garden area.
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.
A bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.

5. Haven Point Inn and Gallery

Haven Point Inn and Gallery
17.9 km from Chestertown Historic District
United States
Joe
RM545
RM605 total
includes taxes & fees
27 Oct - 28 Oct
Haven Point Inn and Gallery
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 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.
A modern living room with a large sofa, a small armchair, a coffee table, and a fireplace.

6. Inn at Huntingfield Creek

Inn at Huntingfield Creek
17.8 km from Chestertown Historic District
United States
Christine
RM572
RM635 total
includes taxes & fees
16 Nov - 17 Nov
Inn at Huntingfield Creek
View all properties

Compare top hotels near Chestertown Historic District

A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.

Comfort Inn & Suites Chestertown

2.3 km from Chestertown Historic District
View
A hotel room with a sofa, two beds, a painting, and a lamp.

Red Roof Inn & Suites Chestertown

2.2 km from Chestertown Historic District
View
A row of motel rooms with stone walls and red doors.

Driftwood Inn

1.6 km from Chestertown Historic District
View
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

The Lodge at Great Oak Landing

13.3 km from Chestertown Historic District
View
A two-story house with a covered porch, a staircase, and a garden area.

Haven Point Inn and Gallery

17.9 km from Chestertown Historic District
View
8.6
Excellent
991 reviews
7.2
Good
511 reviews
5.4
183 reviews
8.0
Very good
122 reviews
9.6
Exceptional
16 reviews
RM402
RM446 total
includes taxes & fees
15 Nov - 16 Nov
RM294
RM326 total
includes taxes & fees
29 Oct - 30 Oct
RM259
RM288 total
includes taxes & fees
27 Oct - 28 Oct
RM441
RM504 total
includes taxes & fees
25 Oct - 26 Oct
RM545
RM605 total
includes taxes & fees
27 Oct - 28 Oct

Top Chestertown Historic District Hotel Reviews

Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG

10/10 Excellent
"Clean room for the night, me and my pup enjoyed our stay!!"
Jeninne 1-night trip
Posted 1 hour ago
Comfort Inn & Suites Aberdeen near APG
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 1 day ago
Hampton Inn & Suites Edgewood/Aberdeen-South
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 2 days 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 2 days ago
Holiday Inn Express Annapolis East-Kent Island 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 3 days ago
WoodSpring Suites Baltimore White Marsh - Nottingham
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 3 days ago
The Inn at Chesapeake Bay Beach Club
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

10/10 Excellent
"Cool spot by a marina. House felt clean and good beds."
Nathaniel Richard 4-night trip
Posted 6 days ago
The Lodge at Great Oak Landing

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.