Chestertown Cottages

Name: Waterfront dog-friendly home with beach just mins to Downtown Annapolis
Address: Annapolis

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Cottages in Chestertown

Amazing views, short walks to great dining!

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

Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,

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

The Heron's Nest at Atlantic Marina

Located in Pasadena, this cottage is on the waterfront, within a 10-minute drive of Fort Smallwood Park and Compass Pointe Golf Courses.

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

With a stay at this cottage, you'll be centrally located in Annapolis, within a 15-minute drive of U.S. Naval Academy and Annapolis Bowl.

Hot Tub

Kitchen

Waterfront River Cottage for 2, dog-friendly

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

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

With a stay at this cottage in Earleville, you'll be near the beach, and 14 mi (22.6 km) from Bohemia Vista Marina and 14.4 mi (23.1 km) from Crow Farm and Vineyard.

Secluded Waterfront Cottage on 200 acre farm near Queenstown

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 6.6 mi (10.6 km) from Hazel Miner Monument.

Kitchen

Washer

Family-Friendly Cottage, Walk to the Beach!

When you stay at this cottage in Kennedyville, you'll be near the beach and 9 minutes by car from Crow Farm and Vineyard.

Eastern Shore beach cottage get-away

With a stay at this cottage in Rock Hall, you'll be a 1-minute walk from Ferry Park and 13 minutes by foot from Waterman’s Museum.

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

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

Be persuaded to experience this vintage cottage by the Sassa

With a stay at this cottage in Galena, you'll be on a river, and 29.4 mi (47.2 km) from University of Delaware and 31.8 mi (51.2 km) from Christiana Mall.

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

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.

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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.