St. Michaels Vacation Rentals

Name: A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Address: Rock Hall

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Vacation Rentals in St. Michaels

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

This vacation home is 3.1 mi (5 km) from Upper Yough River and 4.8 mi (7.7 km) from Bayside History Museum.

Calloway Drive Retreat | House in Shady Side

When you stay at this vacation home in Shady Side, you'll be near the beach and 5 minutes by car from Franklin Point State Park.

Dollhouse in Central Historic St Michaels

With a stay at this vacation home in St. Michaels, you'll be within a 10-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.

Private Waterfront Woods | Dock, Kayaks, Views

With a stay at this vacation home in Annapolis, you'll be on the beach, within a 15-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping Center.

Charming garden row home, easy 4 block walk to the heart of Annapolis.

With a stay at this vacation home in Annapolis (Historic District), you'll be within a 5-minute walk of U.S. Naval Academy and Chase Lloyd House.

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

With a stay at this vacation home in Annapolis (Admiral Heights), you'll be within a 5-minute drive of U.S. Naval Academy and Navy-Marine Corps Memorial Stadium.

Waterfront family resort Lodge with private pier, game room and bar

Located in Centreville, this vacation home is on a river, within a 10-minute drive of Hazel Miner Monument and Earle Landing.

La Maison - Stunning waterfront views with pool

With a stay at this vacation home in Annapolis (Cape St. John), you'll be within a 15-minute drive of U.S. Naval Academy and Broad Creek Marsh.

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

A stay at this vacation home places you in the heart of Annapolis, within a 10-minute walk of U.S. Naval Academy and Ellen O. Moyer Nature Park at Back Creek.

Brand New Spacious Luxury Home

With a stay at this vacation home in Annapolis, you'll be within a 5-minute drive of U.S. Naval Academy and Spa Creek.

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.

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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.