Vacation Homes in St. Michaels
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Featured Vacation Homes in St. Michaels

The Blue Crab Beach House - Free beach passes

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

Dollhouse in Central Historic St Michaels

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

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

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

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

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

Adorable waterside cottage with pool Beach community

PERFECT LOCATION in the heart of history
Top trending hotels in St. Michaels

Waterfront Property, kayaks, private dock, near town
Vacation Rentals in St. Michaels
What kind of vacation do you want in St. Michaels? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in St. Michaels that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in St. Michaels, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
St. Michaels Vacation Homes essential information
Accommodation | 740 Vacation Homes |
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Popular accommodation | The Blue Crab Beach House - Free beach passes , Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Dollhouse in Central Historic St Michaels, Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium, Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything, Adorable waterside cottage with pool Beach community, PERFECT LOCATION in the heart of history, Charming townhome with AC and WiFi in delightful Annapolis |