Upper Marlboro Cottages

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Cottages in Upper Marlboro

Lovely backyard cottage with easy access to metro, shops, dining!

Arlington VA

With a stay at this cottage in Arlington (Ashton Heights), you'll be within a 10-minute drive of National Mall and Smithsonian Institution.

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

North Beach MD

$260 nightly

$276 total

Jan 1 - Jan 2, 2026

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.

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.

Secluded Cozy Cottage in Historic Downtown

Annapolis MD

$448 nightly

$511 total

Dec 15 - Dec 16

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.

Newly Built Tiny Home/Cottage in National Landing/Arlington near DC, & Old Town

Arlington VA

$290 nightly

$331 total

Dec 14 - Dec 15

Total with taxes and fees

Located in Arlington (Aurora Highlands), this cottage is within a 10-minute drive of Smithsonian Institution and National Mall.

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.

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

Stevensville MD

$794 nightly

$877 total

Dec 15 - Dec 16

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.

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.

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.

9 Mi to National Mall: Spacious Bethesda Retreat!

Bethesda MD

Located in Bethesda, this cottage is within a 15-minute drive of Smithsonian Institution and National Mall.

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Churchton MD

Located in Churchton, this cottage is on the waterfront, within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

1 Mi to Old Town: Historic Area Gem in Alexandria

Alexandria VA

With a stay at this cottage in Alexandria (Old Town Alexandria), you'll be within a 15-minute drive of MGM National Harbor Casino and Smithsonian Institution.

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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.