Chesapeake Beach Cottages

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Cottages in Chesapeake Beach

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman MD

Located in Wittman, this cottage is on the waterfront, within a 15-minute drive of Wittman Park and CL Open Field.

Pool

Kitchen

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Tilghman Island MD

With a stay at this cottage in Tilghman, you'll be within a 10-minute walk of Chesapeake Bay and Kronsberg Park.

Kitchen

Washer

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels MD

With a stay at this cottage in St. Michaels (Downtown St. Michaels), you'll be steps from Muskrat Park and St. Michaels Marina.

Pool

Kitchen

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

West River MD

This cottage is 19.1 mi (30.8 km) from U.S. Naval Academy and 3.3 mi (5.2 km) from Franklin Point State Park.

Kitchen

Washer

Lovely 2-bedroom waterfront cottage in charming Wittman

Wittman MD

With a stay at this cottage in Wittman, you'll be within a 15-minute drive of Wittman Park and CL Open Field.

Kitchen

Washer

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels MD

With a stay at this cottage in St. Michaels (Downtown St. Michaels), you'll be steps from Muskrat Park and St. Michaels Marina.

Pool

Kitchen

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

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict MD

$243 nightly

$268 total

May 2 - May 3

Total with taxes and fees

Located in Benedict, this cottage is on the waterfront, a 1-minute drive from Patuxent River and 7 minutes from Running Hare Vineyard.

Free WiFi

Air conditioning

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Edgewater MD

With a stay at this cottage, you'll be centrally located in Edgewater, within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Owings MD

With a stay at this cottage in Owings, you'll be on a river, a 3-minute walk from Fridays Creek Winery and a 4-minute drive from Patuxent River.

Pool

Kitchen

The Yellow Cottage on Harness Creek

Annapolis MD

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

Kitchen

Washer

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman Island MD

With a stay at this cottage in Tilghman, you'll be on the waterfront, within a 5-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

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.