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Search Hotels Near Chestertown Historic District, Chestertown

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Check prices for these dates, 14 – 15 December 2026

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Our top choices for Chestertown Historic District hotels

1. Comfort Inn & Suites Chestertown

A hotel lobby with a fireplace, seating area, and a television.

2. Red Roof Inn & Suites Chestertown

A living room with a fireplace, a television, and a stone accent wall.

3. Driftwood Inn

A row of motel rooms with stone walls and red doors.

4. Inn at Huntingfield Creek

A boat deck with a white bench and a view of a calm lake and distant trees.

5. The Lodge at Great Oak Landing

A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

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.

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Compare popular hotels close to Chestertown Historic District

PropertyProperty classGuest ratingBreakfast includedPoolSpaPet-friendlyWiFi included
A hotel lobby with a fireplace, seating area, and a television.
Comfort Inn & Suites Chestertown		8.6Excellent1,000 reviewsView
A living room with a fireplace, a television, and a stone accent wall.
Red Roof Inn & Suites Chestertown		7.2Good514 reviewsView
A row of motel rooms with stone walls and red doors.
Driftwood Inn		5.4183 reviewsView
A boat deck with a white bench and a view of a calm lake and distant trees.
Inn at Huntingfield Creek		10.0Exceptional74 reviewsView
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
The Lodge at Great Oak Landing		8.0Very good130 reviewsView

Other attractions near Chestertown Historic District

Garfield Center for the Arts at the Prince Theater

Rating: 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

Rating: 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

Rating: 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

Rating: 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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Top Chestertown Historic District Hotel Reviews

Hyatt Place Kent Narrows & Marina

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

Hampton Inn & Suites Edgewood/Aberdeen-South

A modern hotel lobby with a long dining table, several chairs, and a bar area.

The Wildset

A two-story house with a porch, a front door, and a small garden area.

Holiday Inn Express White Marsh by IHG

A modern breakfast area with labeled dispensers for yogurt, eggs, and milk, a coffee machine, and a chalkboard menu.

Graduate by Hilton Annapolis

A spacious atrium with a high ceiling, skylights, and a patterned floor.

Holiday Inn Express & Suites Middletown by IHG

A lobby area with seating, a reception desk, and a refrigerator stocked with beverages.

SpringHill Suites Baltimore White Marsh/Middle River

A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

A buffet area with multiple self-service stations, including trays of omelets and other prepared foods.

Hotel Revival Baltimore

A modern interior with large windows, wooden slats, and green-striped seating.

Hilton Garden Inn Kent Island Marina

A patio with outdoor seating, overlooking a marina with boats.

City Express by Marriott Aberdeen

A hotel entrance with a clear sign reading "LA QUINTA".

Hampton Inn & Suites Baltimore/Aberdeen

A spacious hotel lobby with a large seating area, a television, a fireplace, and a coffee station.

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.