Annapolis Cottages
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Cottages in Annapolis
Secluded Cozy Cottage in Historic Downtown
Annapolis MD
$627 nightly
The price is $714 total per night
$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
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
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
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
Parking included
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Annapolis MD
With a stay at this cottage in Annapolis, you'll be within a 5-minute drive of Chesapeake Bay Bridge and Sandy Point State Park.
Kitchen
Pet friendly
The Red Door Cottage in Eastport - Pet-Friendly!
Annapolis MD
With a stay at this cottage in Annapolis (Eastport), you'll be within a 10-minute drive of U.S. Naval Academy and Historic Mount Moriah AME Church.
Washer
Dryer
Your Annapolis Waterfront retreat - ready for a November or December Annapolis 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
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.
Annapolis Cottages essential information
Accommodation | 15 Cottages |
|---|---|
Lowest Price | $714 |
Highest Price | $714 |
Popular accommodation | Secluded Cozy Cottage in Historic Downtown, The Yellow Cottage on Harness Creek, Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!, NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak, 6 Mi to Dtwn: Family-friendly Home in Annapolis!, Beachfront Home Minutes to Downtown Annapolis Dogs OK, Annapolis Vacation Home: 2 Mi to Quiet Waters Park, Waterfront Annapolis Home: Fire Pit & Fishing Pier, The Red Door Cottage in Eastport - Pet-Friendly!, Your Annapolis Waterfront retreat - ready for a November or December Annapolis getaway!, Annapolis Home Near Beach & Quiet Waters Park!, 2 Mi to Usna: Modern Annapolis Home w/ Fire Pit |