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Compare 51 Cottages in Chestertown with updated reviews, rates, and availability.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (45)

Waterfront dog-friendly home with beach just mins to Downtown Annapolis
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
9.8 out of 10, Exceptional, (29)

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.8 out of 10, Exceptional, (22)

Peaceful getaway convenient to local amenities including beach, boating & food
Peaceful getaway convenient to local amenities including beach, boating & food
9.8 out of 10, Exceptional, (110)

Secluded Waterfront Cottage on 200 acre farm near Queenstown
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (97)

Secluded Cozy Cottage in Historic Downtown
Secluded Cozy Cottage in Historic Downtown
10.0 out of 10, Exceptional, (8)
The price is SAR 1,500
SAR 2,540 total
includes taxes & fees
24 Mar - 25 Mar

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
10.0 out of 10, Exceptional, (26)

Eastern Shore beach cottage get-away
Eastern Shore beach cottage get-away
10.0 out of 10, Exceptional, (133)
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

First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (79)
The price is SAR 368
SAR 592 total
includes taxes & fees
26 Mar - 27 Mar

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, (209)

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

Fairfield Inn & Suites by Marriott White Marsh
5/5 Excellent
"Great hotel and staff!!"
A verified traveler stayed at Fairfield Inn & Suites by Marriott White Marsh
Posted 2 days ago
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