St. Michaels Cottages

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Cottages in St. Michaels

Firefly Cottage at the Cape, Hot Tub, Community beach, Strawberry festival, USNA

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 U.S. Naval Academy.

Hot Tub

Breakfast included

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

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

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

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

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock

Bozman MD

With a stay at this cottage in Bozman, you'll be within a 15-minute drive of Neavitt Park and Perry Cabin Park.

Air conditioning

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

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

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

Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC

Royal Oak MD

When you stay at this cottage in Royal Oak, you'll be 15 minutes by car from Saint Michaels Village.

Kitchen

Washer

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

Rock Hall MD

With a stay at this cottage in Rock Hall, you'll be within a 5-minute drive of Chesapeake Bay and The Mainstay.

Washer

Dryer

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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.