St. Michaels Vacation Rentals

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Vacation Rentals in St. Michaels

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 1-minute drive from U.S. Naval Academy and 12 minutes from Chesapeake Bay Bridge.

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Private 2 Acre Waterfront Family Retreat with Pool & Pier

Cambridge MD

When you stay at this vacation home in Cambridge, you'll be on the waterfront and 14 minutes by car from Christ Rock Park.

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Historic Annapolis Home 1.5 blocks from center of town.

Annapolis MD

A stay at this vacation home places you in the heart of Annapolis, within a 15-minute walk of U.S. Naval Academy and Spa Creek.

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Sweet Bamboo Beach Cottage

north beach MD

When you stay at this vacation home in North Beach, you'll be on the beach, within a 10-minute walk of Chesapeake Bay and Bayside History Museum.

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Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Easton MD

When you stay at this vacation home in Easton, you'll be on the waterfront and 14 minutes by car from Hog Neck Golf Course.

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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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Walking distance to Navy Stadium! No cleaning fees!

Annapolis MD

With a stay at this vacation home in Annapolis (West Annapolis), you'll be within a 15-minute drive of U.S. Naval Academy and Chesapeake Bay Bridge.

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Charming Historic Townhouse Steps From USNA

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 1-minute drive from U.S. Naval Academy and 13 minutes from Chesapeake Bay.

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Historic Home with Parking Steps From Capital & USNA

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 1-minute drive from U.S. Naval Academy and 12 minutes from Chesapeake Bay Bridge.

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Washer

Historic Downtown House with Off Street Parking

Annapolis MD

A stay at this vacation home places you in the heart of Annapolis, within a 15-minute walk of U.S. Naval Academy and Maynard-Burgess House.

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Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Annapolis MD

With a stay at this vacation home in Annapolis (Cape Saint Claire), you'll be a 2-minute drive from Chesapeake Bay and 7 minutes from Chesapeake Bay Bridge.

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Sophisticated Charmer with Parking & Views of the USNA Chapel Dome

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 1-minute drive from U.S. Naval Academy and 14 minutes from Chesapeake Bay.

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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.