Chestertown Cottages

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Cottages in Chestertown

Charming Cottage - Northeast River / Chesapeake Bay

Perryville MD

With a stay at this cottage in Perryville, you'll be within a 5-minute drive of Chesapeake Bay and Chestnut Point Estates and Marina.

Kitchen

Washer

The Heron's Nest at Atlantic Marina

Pasadena MD

When you stay at this cottage in Pasadena, you'll be on the waterfront, just steps from Chesapeake Bay and Northern Chesapeake Bay.

Pool

Kitchen

Secluded Waterfront Cottage on 200 acre farm near Queenstown

Centreville MD

With a stay at this cottage in Centreville, you'll be on the waterfront, and 6.5 mi (10.5 km) from Queenstown Premium Outlets and 6.9 mi (11.2 km) from Queenstown Harbor Golf.

Kitchen

Washer

Eastern shore beachfront cottage with stunning sunset views!

Worton MD

With a stay at this cottage in Worton, you'll be on the beach, within a 15-minute drive of Chesapeake Bay and Betterton Community Park.

Kitchen

Washer

Beachfront Home Minutes to Downtown Annapolis Dogs OK

Annapolis MD

When you stay at this cottage in Annapolis, you'll be on the beach, within a 10-minute walk of Annapolis Sailing School and Annapolis Landing Marina.

Kitchen

Washer

Firefly Cottage at the Cape, Community beach, spring adventures, hot tub, USNA

Annapolis MD

With a stay at this cottage in Annapolis (Cape Saint Claire), you'll be within a 15-minute drive of Chesapeake Bay and U.S. Naval Academy.

Hot Tub

Breakfast included

Secluded Cozy Cottage in Historic Downtown

Annapolis MD

$714 nightly

$814 total

May 4 - May 5

Total with taxes and fees

With a stay at this cottage in Annapolis (Historic District), you'll be within a 15-minute drive of U.S. Naval Academy and Chesapeake Bay Bridge.

Kitchen

Washer

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena MD

$579 nightly

$660 total

May 4 - May 5

Total with taxes and fees

With a stay at this cottage in Pasadena, you'll be within a 10-minute drive of Chesapeake Bay and Fort Smallwood Park.

Kitchen

Washer

Cozy, unique, historic registered cottage on the Corsica River!

Centreville MD

With a stay at this cottage in Centreville, you'll be within a 15-minute drive of Earle Landing and Queenstown Premium Outlets.

Kitchen

Washer

Peaceful getaway convenient to local amenities including beach, boating & food

Rock Hall MD

With a stay at this cottage in Rock Hall, you'll be within a 15-minute walk of Chesapeake Bay and Waterman’s Museum.

Kitchen

Washer

Be persuaded to experience this vintage cottage by the Sassa

Galena MD

Located in Galena, this cottage is on a river, within a 10-minute drive of Galena Town Hall and Galena Town Park.

Kitchen

Washer

Pet Friendly Water View Cottage

Pasadena MD

With a stay at this cottage in Pasadena, you'll be within a 10-minute drive of Chesapeake Bay and Fort Smallwood Park.

Kitchen

Washer

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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.