Annapolis Cottages

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Cottages in Annapolis

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

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

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

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

Walk to Everything - Historic Art’s District

Annapolis MD

With a stay at this cottage, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Asbury United Methodist Church.

Kitchen

Washer

Waterfront Annapolis Home: Fire Pit & Fishing Pier

Annapolis MD

Located in Annapolis, this cottage is a 5-minute drive from Sandy Point State Park and 6 minutes from Chesapeake Bay Bridge.

Kitchen

Dryer

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

Annapolis MD

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

Kitchen

Washer

2 Mi to Usna: Modern Annapolis Home w/ Fire Pit

Annapolis MD

With a stay at this cottage in Annapolis (Admiral Heights), you'll be within a 5-minute drive of U.S. Naval Academy and People's Brewer Hill Cemetery.

Kitchen

Washer

Walk to Lake & Boat Ramp: Central Gem in Annapolis

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 Sandy Point State Park.

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.