St. Michaels Vacation Rentals

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Vacation Rentals in St. Michaels

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

Annapolis MD

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.

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Washer

The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach MD

Located in Owings, this vacation home is within a 5-minute drive of Bayside History Museum and Chesapeake Bay.

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Air conditioning

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Annapolis MD

This vacation home is in the heart of Annapolis, within a 10-minute walk of Maynard-Burgess House and U.S. Naval Academy.

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Washer

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge MD

$339 nightly

$359 total

Dec 13 - Dec 14

Total with taxes and fees

A stay at this vacation home places you in the heart of Cambridge, steps from Long Wharf Park and Choptank River Lighthouse.

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Washer

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Annapolis MD

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

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

Annapolis MD

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 Hammond-Harwood House.

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Washer

Location is perfect and a big bonus we have our own parking at the home!

Annapolis MD

With a stay at this vacation home in Annapolis (Historic District), you'll be within a 10-minute walk of U.S. Naval Academy and 97, 99 and 101 East Street.

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NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge MD

Located in Cambridge, this vacation home is on the waterfront, within a 15-minute drive of Spocott Windmill and Richardson Maritime Museum.

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The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD

Located in Woolford, this vacation home is in a rural location, within a 10-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground Railroad National Historical Park.

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Washer

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels MD

With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Muskrat Park.

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Washer

Waterfront Estate w Private Pier, Game Room & Bar

Centreville MD

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

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Washer

Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & Parking

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Civil Rights Plaque.

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Washer

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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.