Dundalk Cottages

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Cottages in Dundalk

Your Annapolis Waterfront retreat - ready for a winter 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 Navy-Marine Corps Memorial Stadium.

Kitchen

Free WiFi

Peaceful getaway convenient to local amenities including beach, boating & food

Rock Hall MD

With a stay at this cottage in Rock Hall, you'll be a 2-minute walk from Waterman’s Museum and 13 minutes by foot from Ferry Park.

Kitchen

Washer

Secluded Cozy Cottage in Historic Downtown

Annapolis MD

$506 nightly

$577 total

Mar 11 - Mar 12

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

Rock Creek Cottage, Waterfront, Serene Views

Pasadena MD

With a stay at this cottage in Pasadena (Riviera Beach), you'll be within a 10-minute drive of Compass Pointe Golf Courses and Fort Smallwood Park.

Kitchen

Washer

Charming cottage with Pool Access and WiFi in lovely Rock Hall

Rock Hall MD

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

Pool

Free WiFi

Outdoor Pool: Family Retreat - 6 Mi to Dtwn!

Baltimore MD

Located in Baltimore (Cylburn), this cottage is within a 10-minute drive of Maryland Zoo and Johns Hopkins University.

Pool

Kitchen

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

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena MD

$583 nightly

$665 total

Mar 9 - Mar 10

Total with taxes and fees

With a stay at this cottage in Pasadena, you'll be within a 5-minute drive of Compass Pointe Golf Courses and Fort Smallwood Park.

Kitchen

Washer

The Cottage at Merryland Farm

Hydes MD

When you stay at this cottage in Hydes, you'll be within a 10-minute drive of Gunpowder Falls State Park and Boordy Vineyards.

Kitchen

Washer

2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free

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

Firefly Cottage at the Cape, Community beach, spring adventures, fun, bookings.

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

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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.