St. Michaels Vacation Rentals

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Vacation Rentals in St. Michaels

NEW KI Creek Retreat! 3BR/2bath water view, private house near KI wedding venues

Stevensville MD

With a stay at this vacation home in Stevensville, you'll be within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

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

Annapolis MD

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

Kitchen

Washer

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

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 City Dock.

Kitchen

Washer

Recently Renovated Annapolis Home - Conveniently Located

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 City Dock.

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis MD

$634 nightly

$723 total

Aug 24 - Aug 25

Total with taxes and fees

With a stay at this vacation home in Annapolis (Arundel on the Bay), you'll be within a 15-minute drive of Chesapeake Bay and Annapolis City Dock.

Hot Tub

Kitchen

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville MD

$256 nightly

$276 total

Jul 26 - Jul 27

Total with taxes and fees

With a stay at this vacation home in Stevensville, you'll be steps from Chesapeake Bay and Northern Chesapeake Bay.

The Blue Crab Beach House - Free beach passes 🦀

North Beach MD

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

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD

When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis MD

$606 nightly

$691 total

Aug 24 - Aug 25

Total with taxes and fees

With a stay at this vacation home in Annapolis, you'll be within a 10-minute drive of U.S. Naval Academy and Annapolis City Dock.

Charming Historic Annapolis Home With Two Off-street Parking Places!

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, just a 4-minute walk from Annapolis City Dock and 8 minutes by foot from U.S. Naval Academy.

Sophisticated Charmer with Parking & Views of the USNA Chapel Dome

Annapolis MD

A stay at this vacation home places you in the heart of Annapolis, within a 10-minute walk of Annapolis City Dock and U.S. Naval Academy.

Serene Sunsets at Historic Waterfront Home

Annapolis MD

With a stay at this vacation home in Annapolis (Hillsmere), you'll be within a 15-minute drive of Annapolis City Dock and Chesapeake Bay.

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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.