Chesapeake Beach Cottages

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Cottages in Chesapeake Beach

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict MD

$257 nightly

$284 total

Jun 24 - Jun 25

Total with taxes and fees

Located in Benedict, this cottage is on the waterfront, a 1-minute drive from Patuxent River and 7 minutes from Running Hare Vineyard.

Free WiFi

Air conditioning

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 Chesapeake Bay and U.S. Naval Academy.

Kitchen

Washer

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman Island MD

With a stay at this cottage in Tilghman, you'll be on the waterfront, within a 5-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Saint Michaels MD

With a stay at this cottage in St. Michaels (Downtown St. Michaels), you'll be steps from Higgins Yacht Yard and Marina and St. Michaels Marina.

Pool

Kitchen

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

Saint Leonard MD

When you stay at this cottage in St. Leonard, you'll be by the sea, within a 5-minute walk of Chesapeake Bay and Flag Ponds Nature Park.

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

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock

Bozman MD

With a stay at this cottage in Bozman, you'll be within a 15-minute drive of Neavitt Park and Perry Cabin Park.

Air conditioning

Accessible, 3 Season 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 Chesapeake Bay and Romancoke Wharf County Park.

Kitchen

Washer

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Owings MD

With a stay at this cottage in Owings, you'll be on a river, a 3-minute walk from Fridays Creek Winery and a 4-minute drive from Patuxent River.

Pool

Kitchen

Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC

Royal Oak MD

When you stay at this cottage in Royal Oak, you'll be 15 minutes by car from Saint Michaels Village.

Kitchen

Washer

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Edgewater MD

With a stay at this cottage, you'll be centrally located in Edgewater, within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman MD

Located in Wittman, this cottage is on the waterfront, within a 15-minute drive of Wittman Park and CL Open Field.

Pool

Kitchen

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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.