Chesapeake Beach Cottages

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Cottages in Chesapeake Beach

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Annapolis MD

With a stay at this cottage in Annapolis, you'll be on the beach, within a 10-minute drive of Annapolis City Dock and Annapolis Sailing School.

Kitchen

Washer

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels MD

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

Pool

Kitchen

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Tilghman Island MD

With a stay at this cottage in Tilghman, you'll be within a 10-minute walk of Chesapeake Bay and Kronsberg Park.

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.

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.

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge MD

With a stay at this cottage in Cambridge, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Spocott Windmill.

Kitchen

Washer

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

Benedict MD

$263 nightly

$290 total

Aug 24 - Aug 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 Annapolis City Dock and Chesapeake Bay.

Kitchen

Washer

Family and Pet-Friendly, Waterfront with Pier

Cambridge MD

With a stay at this cottage in Cambridge, you'll be on the waterfront, and 5.6 mi (9 km) from Chesapeake Bay and 5.6 mi (9 km) from Northern Chesapeake Bay.

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.

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.

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels MD

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

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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.