Maryland Cottages

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Cottages in Maryland

Shore Point Cottages

9543 Stephen Decatur Hwy Berlin MD

$124 nightly

$138 total

Dec 6 - Dec 7

Total with taxes and fees

With a stay at Shore Point Cottages in Berlin, you'll be within a 10-minute drive of Ocean City Boardwalk and Ocean City Beach.

Pool

Kitchen

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Frederick MD

With a stay at this cottage in Frederick, you'll be within a 5-minute walk of Baker Park and Frederick Memorial Hospital.

Kitchen

Pet friendly

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

North Beach MD

With a stay at this cottage in North Beach, you'll be within a 10-minute walk of Bayside History Museum and Chesapeake Bay.

Washer

Dryer

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.

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

St Michaels MD

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

Pool

Kitchen

Accessible, 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 Romancoke Wharf County Park and Chesapeake Bay.

Kitchen

Washer

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Port Deposit MD

$200 nightly

$211 total

Dec 7 - Dec 8

Total with taxes and fees

This cottage is 1 mi (1.6 km) from Susquehanna River and 5 mi (8 km) from Hollywood Casino.

Air conditioning

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena MD

$583 nightly

$665 total

Dec 8 - Dec 9

Total with taxes and fees

When you stay at this cottage in Pasadena, you'll be within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset

Tall Timbers MD

Located in Tall Timbers, this cottage is on a river, a 3-minute drive from Potomac River and 7 minutes from Piney Point Beach.

Kitchen

Washer

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek MD

Located in Fishing Creek, this cottage is on the waterfront, a 2-minute drive from P. L. Jones Marina and 6 minutes from Chesapeake Bay.

Kitchen

Pet friendly

Comfortable cottage in gated community, 5 mins to OC and Assateague

Berlin MD

$281 nightly

$312 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

With a stay at this cottage in Berlin (Assateague Pointe), you'll be within a 15-minute drive of Ocean City Boardwalk and Assateague Greens Driving Range.

Pool

Kitchen

Soul Oasis - home on the Chesapeake Bay

Lusby MD

Located in Lusby, this cottage is a 1-minute drive from Chesapeake Bay and 7 minutes from Cove Point 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.