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Check prices for these dates

Tonight
6 Nov - 7 Nov
Tomorrow
7 Nov - 8 Nov
This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

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Our top choices for Chestertown Historic District hotels

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

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
2.3 km from Chestertown Historic District
8.6 out of 10, Excellent, (998 reviews)
"Good hotel"
United States
Michael
The price is 2.522.901 ₫
2.800.420 ₫ total
includes taxes & fees
6 Dec - 7 Dec
Comfort Inn & Suites Chestertown
A living room with a fireplace, a television, and a stone accent wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
2.2 km from Chestertown Historic District
7.2 out of 10, Good, (513 reviews)
"Nice clean place and priced good. Plenty of mirrors, plenty of counter space, many tv channels even Christian based ones and comfortable bed. The room needs up dating since damage area on ceiling and corner location rug worn spot. I felt safe as a solo, could check in late and close to historic Chestertown. I would come again."
United States
Regina
The price is 1.848.801 ₫
2.052.169 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.

3. Driftwood Inn

Driftwood Inn
2.0 star property
1.6 km from Chestertown Historic District
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
United States
Kathy
The price is 1.630.744 ₫
1.810.254 ₫ total
includes taxes & fees
7 Nov - 8 Nov
Driftwood Inn
A boat deck with a white bench and a view of a calm lake and distant trees.

4. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
17.8 km from Chestertown Historic District
10.0 out of 10, Exceptional, (74 reviews)
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"
United States
Christine
The price is 3.598.165 ₫
3.994.166 ₫ total
includes taxes & fees
16 Nov - 17 Nov
Inn at Huntingfield Creek
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

5. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
13.3 km from Chestertown Historic District
8.0 out of 10, Very good, (127 reviews)
"Nice restairant and bar"
United States
Steve allen
The price is 2.773.548 ₫
3.170.997 ₫ total
includes taxes & fees
8 Nov - 9 Nov
The Lodge at Great Oak Landing
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

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A hotel lobby with a fireplace, seating area, and a television.
Comfort Inn & Suites Chestertown
2.5 star property
8.6
Excellent
998 reviews
View
A living room with a fireplace, a television, and a stone accent wall.
Red Roof Inn & Suites Chestertown
2.0 star property
7.2
Good
513 reviews
View
A row of motel rooms with stone walls and red doors.
Driftwood Inn
2.0 star property
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
3.5 star property
10.0
Exceptional
74 reviews
View
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
The Lodge at Great Oak Landing
3.5 star property
8.0
Very good
127 reviews
View

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.
See properties

Top Chestertown Historic District Hotel Reviews

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville

10/10 Excellent

Hotel was spotlessly clean, bed was super comfy, view from room was beautiful,staff member at check in Paul was very friendly and helpful
United Kingdom
Pamela
Reviewed November 3, 2025
Hyatt Place Kent Narrows & Marina

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.

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.