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Check-in
29 Aug 2026
Check-out
30 Aug 2026
Guests
2 guests

Adults:

2

Children:

0

10 accommodations in Maryland

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Lodging At The Imperial 6 photos

Lodging At The Imperial

208 High Street
Exceptional location

Located around a 25-minute stroll from Chesapeake Movies, Lodging At The Imperial Hotel Chestertown offers access to tourist attractions throughout Chestertown. Guests who stay at this Chestertown…

Free cancellation
From 194 US$ per night
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Carriage House Hideaway In Center Of Chestertown 6 photos

Carriage House Hideaway In Center Of Chestertown

North Mill Street 214, Unit B
Free Wi-Fi Exceptional location

Nestled only 5 minutes on foot from Christ United Methodist Church, the 1-room Carriage House Hideaway In Center Of Chestertown Apartment offers quick access to numerous tourist attractions nearby.

Free cancellation
From 126 US$ per night
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Pet-Friendly Home On Chester River W/ Dock! 6 photos

Pet-Friendly Home On Chester River W/ Dock!

205 Fey Rd
Free Wi-Fi Pleasant location

The 5-bedroom Pet-Friendly Home On Chester River With Dock! is located 10 minutes by car from Twigs & Teacups Gift Shop and provides canoeing for active guests. Located 25 minutes' stroll from Kent…

Free cancellation
From 793 US$ per night
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Driftwood Inn 6 photos

Driftwood Inn

2.9 Average 59 reviews
609 Washington Avenue
Free Wi-Fi Very good location

Located nearly 15 minutes on foot from Chesapeake Movies, the 2-star Driftwood Inn Chestertown offers Wi-Fi in public areas and parking. Located only 1.8 km from a convenient place to shop such as…

Free cancellation
From 57 US$ per night
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Comfort Inn & Suites Chestertown 6 photos

Comfort Inn & Suites Chestertown

4.1 Excellent 259 reviews
150 Scheeler Road
Free Wi-Fi Superb location Breakfast

Offering a location within 500 metres of Presbyterian Church of Chestertown, Comfort Inn & Suites Chestertown offers 81 rooms. All guests can enjoy Wi-Fi in public areas and access to a fitness…

Free cancellation
From 92 US$ per night
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Quality Suites 6 photos

Quality Suites

4 Good 49 reviews
160 Scheeler Rd.

Located 2.9 km from such natural attractions as Wilmer Park, the comfortable Quality Suites Chestertown hotel includes a laundromat. Boasting a swimming pool and a gym area, this 3-star hotel offers…

Free cancellation
From 75 US$ per night
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Brampton Inn 6 photos

Brampton Inn

4.5 Excellent 18 reviews
25227 Chestertown Road
Free Wi-Fi Exceptional location Breakfast

The luxurious Brampton 1860 Bed & Breakfast Chestertown has 13 rooms and is located around 3 km from the Pam Foss Sculpture Gallery. A garden adorned with an outdoor seating enhances the ambiance of…

Free cancellation
From 337 US$ per night
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