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Hotels near Chestertown Historic District

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This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

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Our top choices for Chestertown Historic District hotels

Free daily full breakfast

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, (929 reviews)
"Great visit"
United States
Danielle
The price is S$154
includes taxes & fees
23 Jul - 24 Jul
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, (458 reviews)
"Perfect for an overnight trip, staff was very helpful."
United States
Anasmel
The price is S$103
includes taxes & fees
9 Jul - 10 Jul
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, (177 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 S$91
includes taxes & fees
6 Jul - 7 Jul
Driftwood Inn
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
13.3 km from Chestertown Historic District
7.8 out of 10, Good, (89 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again "
United States
Nicola
The price is S$196
includes taxes & fees
12 Jul - 13 Jul
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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Top Chestertown Historic District Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Staff was friendly, helpful and wonderful. Room was good, location is great."
LAURA 3-night trip
Posted less than an hour ago
Historic Inns of Annapolis

Hotels near other Chestertown Historic District attractions

Washington College

8.6/10 (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 16 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 16 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.