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Search Chestertown Cottage Rentals from CA $495
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Browse Select Chestertown Cottages

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
10.0 out of 10, Exceptional, (93)

The Heron's Nest at Atlantic Marina
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, (301)

Secluded Waterfront Cottage on 200 acre farm near Queenstown
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (103)

Eastern Shore beach cottage get-away
Eastern Shore beach cottage get-away
10.0 out of 10, Exceptional, (136)

Charming, updated 1930's beachfront cottage with stunning sunset views
Charming, updated 1930's beachfront cottage with stunning sunset views

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
10.0 out of 10, Exceptional, (50)

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (54)

Secluded Cozy Cottage in Historic Downtown
Secluded Cozy Cottage in Historic Downtown
9.4 out of 10, Exceptional, (13)
The price is CA $687
CA $1,111 total
includes taxes & fees
Aug 17 - Aug 18
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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Top Chestertown Hotel Reviews

Historic Inns of Annapolis
10/10 Excellent
Find out more about Chestertown
Find out more about Chestertown
Chestertown Cottages information
Number of reviews | 965 |
---|---|
Accommodation | 57 Cottages |
Lowest Price | CA $495 |
Highest Price | CA $687 |
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