Orchard Beach Cottages

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Cottages in Orchard Beach

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

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Rosedale MD

$431 nightly

$498 total

Dec 8 - Dec 9

Total with taxes and fees

With a stay at this cottage in Rosedale, you'll be within a 15-minute drive of Baltimore Inner Harbor Marina and Johns Hopkins University.

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

Outdoor Pool & Hot Tub: Retreat - 6 Mi to Dtwn!

Baltimore MD

With a stay at this cottage in Baltimore (Cylburn), you'll be within a 15-minute drive of Johns Hopkins University and Baltimore Inner Harbor Marina.

Pool

Kitchen

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

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

annapolis MD

With a stay at this cottage, you'll be centrally located in Annapolis, within a 15-minute drive of U.S. Naval Academy and Annapolis Bowl.

Hot Tub

Kitchen

6 Mi to Dtwn: Family-friendly Home in Annapolis!

Annapolis MD

With a stay at this cottage in Annapolis, you'll be within a 10-minute drive of U.S. Naval Academy and Annapolis Harbour Center.

Kitchen

Pet friendly

Rare find! Chic cottage, salt water heated pool May 15-Oct15.

Arnold MD

With a stay at this cottage in Arnold, you'll be within a 15-minute drive of U.S. Naval Academy and Bay Hills Golf Club.

Pool

Kitchen

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

Eastern Shore beach cottage get-away

Rock Hall MD

With a stay at this cottage in Rock Hall, you'll be just steps from Ferry Park and Chesapeake Bay.

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

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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.