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Compare 16 Guest Houses in Chestertown with updated reviews, rates, and availability.

Island Life! Kent Island Waterfront with Pool-Bring your boat!
Island Life! Kent Island Waterfront with Pool-Bring your boat!
10.0 out of 10, Exceptional, (186)

Calico Cottage Guest House
Calico Cottage Guest House
10.0 out of 10, Exceptional, (8)

Top Floor East Handicap Accessible
Top Floor East Handicap Accessible
The price is AED 1,233
AED 1,774 total
includes taxes & fees
13 May - 14 May

Center Parlor Room at Sandy Cove
Center Parlor Room at Sandy Cove
The price is AED 1,326
AED 1,872 total
includes taxes & fees
15 May - 16 May

First Floor Bay View Deluxe Suite
First Floor Bay View Deluxe Suite
The price is AED 1,465
AED 2,020 total
includes taxes & fees
20 May - 21 May

Top Floor Deluxe Suite Bay View
Top Floor Deluxe Suite Bay View
The price is AED 1,465
AED 2,020 total
includes taxes & fees
26 May - 27 May

Top Floor Handicap Accessible Bay View
Top Floor Handicap Accessible Bay View
The price is AED 1,326
AED 1,872 total
includes taxes & fees
14 May - 15 May

First Floor Family Deluxe Suite
First Floor Family Deluxe Suite
The price is AED 1,233
AED 1,774 total
includes taxes & fees
13 May - 14 May
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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Other property types in Chestertown

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (215)

BAYSIDE BUNGALOW
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (35)
The price is AED 643
AED 1,001 total
includes taxes & fees
13 May - 14 May

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.6 out of 10, Exceptional, (24)
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.
Recent reviews of Chestertown hotels
Recent reviews of Chestertown hotels

Fairfield Inn & Suites by Marriott White Marsh
5/5 Excellent
"The property was in a great location near lots of Transportation but it was quiet and I couldn't hear any traffic noise. Everybody I came in contact with was courteous and friendly and the breakfast was really good the coffee was great."
A verified traveler stayed at Fairfield Inn & Suites by Marriott White Marsh
Posted 1 day ago
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