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

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

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 within a 15-minute drive of Chesapeake Bay and Annapolis City Dock.

Hot Tub

Breakfast included

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

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

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

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

Your Annapolis Waterfront retreat for a weekend or any-day getaway!

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

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

Cozy and serene one bedroom waterfront guest cottage

Crownsville MD

With a stay at this cottage in Crownsville (Herald Harbor), you'll be within a 15-minute drive of Joyces Marina and Annapolis Bowl.

Kitchen

Water view

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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.