Highland Beach Cottages

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Cottages in Highland Beach

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

North Beach MD

$261 nightly

$277 total

Dec 6 - Dec 7

Total with taxes and fees

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.

Pool

Kitchen

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

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

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, you'll be just steps from Muskrat Park and St. Michaels Marina.

Pool

Kitchen

The Middle Point Cabin in Saint Michaels

Neavitt MD

When you stay at this cottage in Neavitt, you'll be steps from Neavitt Park.

Kitchen

Washer

Charming Waterfront Cottage Retreat near St. Michaels

Bozman MD

When you stay at this cottage in Bozman, you'll be 14 minutes by car from Neavitt Park.

Kitchen

Washer

Secluded Cozy Cottage in Historic Downtown

Annapolis MD

$627 nightly

$714 total

Jan 3 - Jan 4, 2026

Total with taxes and fees

With a stay at this cottage in Annapolis (Historic District), you'll be within a 15-minute walk of U.S. Naval Academy and 14 Fleet Street.

Kitchen

Washer

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 U.S. Naval Academy and Maryland Quiet Waters Park.

Kitchen

Washer

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Stevensville MD

$802 nightly

$885 total

Dec 8 - Dec 9

Total with taxes and fees

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

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!

Annapolis MD

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 Chesapeake Bay.

Hot Tub

Breakfast included

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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.