Annapolis Junction Cottages

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Cottages in Annapolis Junction

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

Pets Welcome: Quiet Silver Spring Retreat!

Silver Spring MD

When you stay at this cottage in Silver Spring, you'll be within a 10-minute drive of Olney Theatre Center and Patuxent River State Park.

Pool

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

Vacation Rental w/ Yard in Washington, DC, Area

Washington DC

Located in Washington (Northeast), this cottage is within a 10-minute drive of Smithsonian Institution and United States Capitol.

Kitchen

Parking included

DC Area Home: 1 Mi to Light Rail!

Silver Spring MD

With a stay at this cottage in Silver Spring, you'll be within a 10-minute drive of Holy Cross Hospital and Rock Creek Park.

Kitchen

Parking 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.