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Compare 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, (183)

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 SAR 1,316
SAR 1,872 total
includes taxes & fees
9 Apr - 10 Apr

Center Parlor Room at Sandy Cove
Center Parlor Room at Sandy Cove
The price is SAR 1,415
SAR 1,977 total
includes taxes & fees
13 Apr - 14 Apr

First Floor Bay View Deluxe Suite
First Floor Bay View Deluxe Suite
The price is SAR 1,564
SAR 2,135 total
includes taxes & fees
9 Apr - 10 Apr

Top Floor Deluxe Suite Bay View
Top Floor Deluxe Suite Bay View
The price is SAR 1,564
SAR 2,135 total
includes taxes & fees
9 Apr - 10 Apr

First Floor Family Deluxe Suite
First Floor Family Deluxe Suite
The price is SAR 1,316
SAR 1,872 total
includes taxes & fees
9 Apr - 10 Apr

Second Floor Standard Deluxe Bay View
Second Floor Standard Deluxe Bay View
The price is SAR 1,415
SAR 1,977 total
includes taxes & fees
9 Apr - 10 Apr
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

Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
9.8 out of 10, Exceptional, (22)

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, (210)

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
10.0 out of 10, Exceptional, (180)
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

Comfort Inn & Suites Chestertown
5/5 Excellent
"Check-in was quick & easy. The gentleman at the desk was wonderfully pleasant and very welcoming. Our room was clean and spacious. Beds were clean and comfortable. "
A verified traveler stayed at Comfort Inn & Suites Chestertown
Posted 11 hours ago
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