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Find hotels in Chestertown, MD from $80

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Hidden gem with water and golf course views! Bike ride to downtown!
Country Estate in Historic District
1.53 mi from city center
5/5 Exceptional! (28 reviews)
Fantastic!
"Bob and Beth’s place is beautiful, clean, and comfortable. We enjoyed cooking in the spacious kitchen and walking through the beautiful gardens. We loved our stay and will definitely be back!"

Reviewed on May 2, 2022

Country Estate in Historic District
Quaint cottage with amazing sunset views to soak up nature
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Driftwood Inn
2 out of 5
609 Washington Avenue, Chestertown, MD, 21620
The price is $80 per night from May 24 to May 25
1.84 mi from city center
2.3/5 (141 reviews)
Hunting weekend excursion
"Staff was courteous and responsive Rooms met expectations Our hunting party of 2 adults and 2 youths were comfortable Throughout our stay."

Reviewed on Nov 15, 2021

Driftwood Inn
Great Oak Manor
3.5 out of 5
10568 Cliff Rd, Chestertown, MD, 21620
7.2 mi from city center
4.7/5 Exceptional! (44 reviews)
"Plenty of privacy"

Reviewed on Feb 15, 2022

Great Oak Manor
Historic downtown Chestertown Home. #1 Location.
1.33 mi from city center
5/5 Exceptional! (6 reviews)
Great house and location!
"The house is really cute. Location is great as it is a short walk to the middle of Chestertown shops and restaurants. Also near the water! Washington college is just around the corner - so great if you need a place to stay if you have a Washington college kid. The host were great with communication ..."

Reviewed on Feb 14, 2022

Historic downtown Chestertown Home. #1 Location.
Circa 1900 Home in the Heart of Historic Downtown Chestertown
1.66 mi from city center
5/5 Exceptional! (27 reviews)
Alumni weekend stay
"Absolutely loved staying here! This place was beautiful and exactly what we hoped for."

Reviewed on May 1, 2022

Circa 1900 Home in the Heart of Historic Downtown Chestertown
Charming  Chestertown Waterfront Cottage
3.48 mi from city center
4.9/5 Exceptional! (30 reviews)
Peaceful Getaway
"The property is as described in the photos. The owner had nice thoughtful touches for us upon arrival. The house was very clean, the kitchen well stocked for use, and the beds very comfortable. We enjoyed sitting on the outdoor patio with a view of the water and used the fire pit outside every night. ..."

Reviewed on May 1, 2022

Charming Chestertown Waterfront Cottage
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
4.8/5 Exceptional! (34 reviews)
Great place
"This house is amazing, comfy, great view"

Reviewed on Oct 4, 2021

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
5/5 Exceptional! (60 reviews)
Wonderful stay, even better than description
"We had a wonderful experience. Beth made sure we had any questions answered. The house is bigger than what the pictures show and it's very well equipped."

Reviewed on Jan 20, 2022

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
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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 information

Number of reviews 370
Accommodation 462 hotels
Lowest Price $80
Highest Price $80

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