Chestertown Cottages

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Cottages in Chestertown

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

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Annapolis MD

With a stay at this cottage in Annapolis, you'll be on the beach, within a 10-minute drive of Annapolis City Dock and Annapolis Sailing School.

Kitchen

Washer

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

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

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.

Pool

Kitchen

Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.

Annapolis MD

With a stay at this cottage in Annapolis (West Annapolis), you'll be within a 5-minute drive of U.S. Naval Academy and Annapolis City Dock.

Kitchen

Free WiFi

Waterfront River Cottage for 2, dog-friendly

Severna Park MD

Located in Severna Park, this cottage is by the ocean, within a 10-minute drive of B&A Trail and Severna Park Golf Center.

Kitchen

Pet friendly

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

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

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

Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football.

Annapolis MD

With a stay at this cottage in Annapolis (Cape Saint Claire), you'll be a 2-minute drive from Chesapeake Bay and 6 minutes from Sandy Point State Park.

Hot Tub

Breakfast included

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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.