Jessup Cottages
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Cottages in Jessup
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena MD
$583 nightly
The price is $665 total per night
$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
The price is $498 total per night
$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
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
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
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.
Jessup Cottages essential information
Accommodation | 73 Cottages |
|---|---|
Lowest Price | $498 |
Highest Price | $714 |
Popular accommodation | Chesapeake Cottages- 2 Quaint Waterfront Retreats, 5 Mi to Downtown Baltimore: Quiet Home w/ Porch, Secluded Cozy Cottage in Historic Downtown, Outdoor Pool & Hot Tub: Retreat - 6 Mi to Dtwn!, 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, Pets Welcome: Quiet Silver Spring Retreat!, 6 Mi to Dtwn: Family-friendly Home in Annapolis!, Rare find! Chic cottage, salt water heated pool May 15-Oct15. , Vacation Rental w/ Yard in Washington, DC, Area, DC Area Home: 1 Mi to Light Rail!, 6 Mi to Inner Harbor - Family Home w/ Fenced Yard! |