Book Holiday Homes in St. Michaels
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Featured Holiday 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

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

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
St. Michaels Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our St. Michaels vacation homes are the perfect way for you to wing it.
Holiday houses in St. Michaels let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of St. Michaels in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local St. Michaels adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in St. Michaels with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of St. Michaels vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
St. Michaels Holiday Homes essential information
Accommodation | 740 Holiday Homes |
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Lowest Price | |
Highest Price | |
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, The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, 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 |
More accommodations in St. Michaels
Top trending hotels in St. Michaels

St Michaels Inn

Inn at Perry Cabin

The Wildset

Waterfront Property, kayaks, private dock, near town
More ways to explore St. Michaels
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^Subject to availability and chosen travel dates.