Chestertown Cottages

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Cottages in Chestertown

Firefly Cottage at the Cape, Hot Tub, Community beach, summer fun, USNA visits.

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

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

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville MD

With a stay at this cottage in Earleville, you'll be near the beach, within a 15-minute drive of Chesapeake Bay and Earleville Wildlife Management Area.

Kitchen

Washer

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

Cozy 3-bedroom cottage in water-privileged community minutes from Annapolis, MD

Severna Park MD

When you stay at this cottage in Severna Park, you'll be near the beach, within a 15-minute drive of U.S. Naval Academy and Chesapeake Bay.

Kitchen

Washer

Life is better at the RIVER!--Cozy waterfront cottage

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

Free WiFi

Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Navy Sports visitors and the Annapolis Blues games!

Annapolis MD

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

Kitchen

Free WiFi

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

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Stevensville MD

With a stay at this cottage in Stevensville, you'll be within a 5-minute drive of Chesapeake Bay and Romancoke Wharf County Park.

Kitchen

Washer

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 beach cottage get-away

Rock Hall MD

With a stay at this cottage in Rock Hall, you'll be steps from Chesapeake Bay and Ferry Park.

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

Rock Hall MD

With a stay at this cottage in Rock Hall, you'll be within a 5-minute drive of Chesapeake Bay and The Mainstay.

Washer

Dryer

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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.