Compare Hotels with a Wedding Venue in Chestertown

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Featured Chestertown Hotels with a Wedding Venue

Driftwood Inn

Driftwood Inn

2 out of 5
609 Washington Avenue Chestertown MD
$64 nightly
The price is $70 total per night
$70 total
Dec 24 - Dec 25
Total with taxes and fees
With a stay at Driftwood Inn in Chestertown, you'll be a 3-minute walk from Washington College and 12 minutes by foot from Rolling Road Park.
Pet friendly
Parking included
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
$103 nightly
The price is $114 total per night
$114 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
When you stay at Comfort Inn & Suites Chestertown in Chestertown, you'll be in the historical district, within a 5-minute drive of Washington College and Historical Society of Kent County Maryland.
Pool
Breakfast included
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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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Chestertown hotels essential information

Accommodation
1,084 hotels
Lowest Price
$70
Highest Price
$114
Popular hotels
Driftwood Inn, Comfort Inn & Suites Chestertown

Most Recent Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"Clean room, great location, very friendly and helpful staff"
A verified traveler from Currie stayed at Best Western Plus Hotel & Conference Center
Best Western Plus Hotel & Conference Center

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