Book Holiday Homes in Stevensville
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Featured Holiday Homes in Stevensville

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

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
Stevensville 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 Stevensville vacation homes are the perfect way for you to wing it.
Holiday houses in Stevensville 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 Stevensville 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 Stevensville adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Stevensville 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 Stevensville 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.
Stevensville Holiday Homes essential information
Accommodation | 793 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, 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 |
More accommodations in Stevensville
Top trending hotels in Stevensville

The Inn at Chesapeake Bay Beach Club

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Circa 1700 Chesapeake Colonial home on the National Register.

Relax on Kent Island in 3 Bedroom Home w/Waterview
More ways to explore Stevensville
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^Subject to availability and chosen travel dates.