St. Michaels Cottages

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Cottages in St. Michaels

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

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

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

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

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

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

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

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

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge MD

With a stay at this cottage in Cambridge, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Spocott Windmill.

Kitchen

Washer

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Saint Michaels MD

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

Pool

Kitchen

Family and Pet-Friendly, Waterfront with Pier

Cambridge MD

With a stay at this cottage in Cambridge, you'll be on the waterfront, and 5.6 mi (9 km) from Chesapeake Bay and 5.6 mi (9 km) from Northern Chesapeake Bay.

Pool

Kitchen

Charming 1-bedroom cottage with AC in cozy Harwood

Harwood MD

This cottage is 8.4 mi (13.5 km) from Chesapeake Bay and 9.5 mi (15.3 km) from U.S. Naval Academy.

Kitchen

Pet friendly

"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

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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.