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Check prices for these dates

This weekend
22 May - 24 May
Next weekend
29 May - 31 May

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Our top choices for Chestertown Historic District hotels

Exterior

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, (912 reviews)
"Great visit"
United States
Danielle
The price is ฿3,656
฿4,058 total
includes taxes & fees
17 Jun - 18 Jun
Comfort Inn & Suites Chestertown
Lobby lounge

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, (440 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is ฿2,341
฿2,598 total
includes taxes & fees
31 May - 1 Jun
Red Roof Inn & Suites Chestertown
Front of property – evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
1.6 km from Chestertown Historic District
5.2 out of 10, (176 reviews)
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
United States
Gabriel
The price is ฿2,065
฿2,292 total
includes taxes & fees
20 May - 21 May
Driftwood Inn
Private beach nearby, sun-loungers, beach volleyball

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, (82 reviews)
"clean, comfortable, and staff was friendly and helpful. "
United States
Gail
The price is ฿4,301
฿4,918 total
includes taxes & fees
27 May - 28 May
The Lodge at Great Oak Landing
Lake

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, (63 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
The price is ฿5,790
฿6,427 total
includes taxes & fees
16 Jun - 17 Jun
Inn at Huntingfield Creek
Exterior

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
17.9 km from Chestertown Historic District
10.0 out of 10, Exceptional, (1 review)
"Room was very clean and the owner was very helpful will definitely stay there again"
United States
John
The price is ฿5,040
฿5,594 total
includes taxes & fees
26 May - 27 May
Haven Point Inn and Gallery
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
Exterior
Comfort Inn & Suites Chestertown
2.5 star property
8.6
Excellent
912 reviews
View
Lobby lounge
Red Roof Inn & Suites Chestertown
2.0 star property
7.2
Good
440 reviews
View
Front of property – evening/night
Driftwood Inn
2.0 star property
5.2
176 reviews
View
Private beach nearby, sun-loungers, beach volleyball
The Lodge at Great Oak Landing
3.5 star property
8.0
Very good
82 reviews
View
Lake
Inn at Huntingfield Creek
3.5 star property
10.0
Exceptional
63 reviews
View

Top Chestertown Historic District Hotel Reviews

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

4/10 Poor
"Room had cobwebs on the windows inside, towel bars fell apart, toilet paper holders not attached, just a post sticking out of walls. Property was not maintained outside was cigar butts that laid on sidewalk for 3 days that we were there, someone broke a glass beer bottle that was not cleaned up. Very disappointing as I am a Hilton Honors member. I tried to book through Hilton and showed no rooms available for the dates we needed to be there for our family wedding. Over priced for quality of room and property! Very disappointed with our experience."
Ronald 3-night trip
Posted 9 hours ago
Hilton Garden Inn Kent Island Marina

Hotels near other Chestertown Historic District attractions

Washington College

4.3/5 (87 reviews)
Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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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 18 hotels and other accommodation options you'll find within a mile.
What's the best place to stay close to Chestertown Historic District?
Holiday Inn Express Annapolis East-Kent Island by IHG 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 18.9 mi (30.5 km) from Chestertown Historic District. Other good options around the area include Best Western Kent Narrows Inn and Hyatt Place Kent Narrows & Marina.
How many hotels should I expect to find near Chestertown Historic District?
Expedia has 18 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.