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Featured Chestertown Kid Friendly Hotels

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

$103 nightly

$115 total

Jul 12 - Jul 13

Total with taxes and fees

Free Cancellation

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

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chestertown MD

Located in Chestertown, this vacation home is on the waterfront, within a 10-minute drive of Chestertown Dog Park and Washington College.

Breakfast included

Kitchen

Driftwood Inn

609 Washington Avenue Chestertown MD

$64 nightly

$70 total

Jun 18 - Jun 19

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

With a stay at Driftwood Inn in Chestertown, you'll be a 3-minute walk from Washington College and 11 minutes by foot from Larrabee Arts Center.

Pet friendly

Parking 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.

Chestertown hotels essential information

Accommodation	1,091 hotels
Lowest Price	$70
Highest Price	$115
Popular hotels	Comfort Inn & Suites Chestertown, Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town, Driftwood Inn

Most Recent Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5

Posted 5 hours ago

CheapTickets Verified Review

"When we arrived people were still checking out because of the problem with the elevators. So we have to wait for the room to be cleaned. We booked a handicap room but was giving a standard room I called down to the desk and they did move us to a handicap room. The Restaurant was closed for remodeling. One of the two elevators was not working. The hallways were hot. The a/c was working in our room just fine. It could be a nice place to stay. The location is great for someone that wants to shop etc. I felt it was a little pricey."

A verified traveler stayed at Annapolis Waterfront Hotel, Autograph Collection