Chesapeake Beach Cottages

Name: Pet-friendly Annapolis Home: Walk to Beach!
Address: Annapolis

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Cottages in Chesapeake Beach

Cozy Cottage with access to and partially obstructed views of the bay.

Located in Port Republic, this cottage is in a rural location, within a 10-minute drive of Matoaka Beach and R&J's PlayPark.

Kitchen

Washer

Family and Pet-Friendly, Waterfront with Pier

With a stay at this cottage in Cambridge, you'll be on the waterfront, and 6.3 mi (10.1 km) from Ragged Island and 7.6 mi (12.2 km) from Spocott Windmill.

Pool

Kitchen

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

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

Kitchen

Washer

Eastern Shore Waterside Cottage Near St. Michaels

When you stay at this cottage in Neavitt, you'll be on the waterfront and 3 minutes by foot from Neavitt Park.

Pool

Kitchen

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

With a stay at this cottage, you'll be centrally located in Edgewater, within a 15-minute drive of Sand Point Marsh and South River Golf Links.

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Washer

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

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

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Washer

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

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.

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Washer

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

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

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Washer

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

With a stay at this cottage in St. Leonard, you'll be by the sea, just a 4-minute walk from Flag Ponds Nature Park and 9 minutes by foot from Flag Harbor Marina.

Hot Tub

Kitchen

North Beach Cottage - Walk to Chesapeake Bay

Located in North Beach, this cottage is by the sea, a 3-minute walk from Bayside History Museum and within a 5-minute drive of Chesapeake Beach Water Park.

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Washer

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

Located in Tilghman, this cottage is on the waterfront, within a 5-minute drive of Tilghman Watermen’s Museum and Talbot County Library Tilghman Branch.

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Washer

Pet-friendly Annapolis Home: Walk to Beach!

With a stay at this cottage in Annapolis (Oyster Harbor), you'll be within a 15-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping Center.

Kitchen

Pet friendly

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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.