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Check prices for these dates

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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Our top choices for Chestertown Historic District hotels

A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.
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
1.4 mi from Chestertown Historic District
United States
Amy
£87
includes taxes & fees
25 Oct - 26 Oct
Comfort Inn & Suites Chestertown
A multi-story brick building with a covered entrance and a parking lot.
A living room with a fireplace, a television, and a stone accent wall.
A spacious living room with a fireplace, a stone accent wall, and a television mounted above it.
A hotel room with a bed, a sofa, a desk, and a painting on the wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
1.3 mi from Chestertown Historic District
United States
Linda
£60
includes taxes & fees
11 Oct - 12 Oct
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A two-story building with a brick facade, large windows, and a sloped roof.
A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.
A living room with a wooden cabinet, a television, a sofa, and a dining table.

3. Driftwood Inn

Driftwood Inn
1 mi from Chestertown Historic District
United States
Kathy
£53
includes taxes & fees
1 Oct - 2 Oct
Driftwood Inn
A two-story house with a covered porch, a staircase, and a garden area.
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 garden with a lawn and a table with chairs under a canopy.
A bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.

4. Haven Point Inn and Gallery

Haven Point Inn and Gallery
11.1 mi from Chestertown Historic District
United States
Mary
£112
includes taxes & fees
15 Oct - 16 Oct
Haven Point Inn and Gallery
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Top Chestertown Historic District Hotel Reviews

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

8/10 Good
"Decent place to stay, good price."
Antonio 4-night trip
Posted 11 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Nice room. Nice stay."
Lyn 2-night trip
Posted 13 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

8/10 Good
"The room was just ok nothing spectacular about the room/ decors The caulking around bathroom area looked like half was missing we had water view For a new hotel and the cost I would of expected better"
Carol 2-night trip
Posted 20 hours ago
Hyatt Place Kent Narrows & Marina
SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River

8/10 Good
"The Staff"
Marcia 1-night trip
Posted 1 day ago
SpringHill Suites Baltimore White Marsh/Middle River
Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG

8/10 Good
"This Holiday Inn is not too far from my location and I take care of my guests there. It is a value for the money and includes parking and breakfast. I would recommend."
Stephanie 1-night trip
Posted 3 days ago
Holiday Inn Express White Marsh by IHG
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Good stay. I wish I could have used the spa. It was closed on tuesdays. I also wish they could have provided free breakfast for the price that they charge per room"
Rathna 1-night trip
Posted 4 days ago
The Inn at Chesapeake Bay Beach Club
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Pet friendly. Full breakfast. Desk was accommodating for a ground floor room for my dog. Room was clean and comfortable."
Wayne 1-night trip
Posted 6 days ago
Holiday Inn Express Annapolis East-Kent Island by IHG

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?
The Lodge at Great Oak Landing is one of the top choices for your stay based on our traveller data, and this lodge offers a golf course and 2 restaurants. You'll find it 8.3 mi (13.3 km) from Chestertown Historic District. Other good options around the area include Hilton Garden Inn Kent Island Marina and Holiday Inn Express Annapolis East-Kent Island by IHG.
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.