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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, (184)

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 1,315
SAR 1,871 total
includes taxes & fees
30 Apr - 1 May

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
30 Apr - 1 May

First Floor Bay View Deluxe Suite
First Floor Bay View Deluxe Suite
The price is SAR 1,564
SAR 2,134 total
includes taxes & fees
30 Apr - 1 May

Top Floor Deluxe Suite Bay View
Top Floor Deluxe Suite Bay View
The price is SAR 1,564
SAR 2,134 total
includes taxes & fees
1 May - 2 May

Top Floor Handicap Accessible Bay View
Top Floor Handicap Accessible Bay View
The price is SAR 1,415
SAR 1,977 total
includes taxes & fees
8 May - 9 May

First Floor Family Deluxe Suite
First Floor Family Deluxe Suite
The price is SAR 1,315
SAR 1,871 total
includes taxes & fees
30 Apr - 1 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

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

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, (212)

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.
9.4 out of 10, Exceptional, (23)
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

Hilton Garden Inn Baltimore/White Marsh
5/5 Excellent
"My only issue was my dog is a ESA and was still charged the Pet fee. "
A verified traveler stayed at Hilton Garden Inn Baltimore/White Marsh
Posted 15 hours ago
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