Book Holiday Homes in St. Michaels

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Featured Holiday Homes in St. Michaels

The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach
Located in North Beach, this vacation home is by the sea, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
The Blue Crab Beach House - Free beach passes
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

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

Annapolis
A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and Marina.
Dollhouse in Central Historic St Michaels
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Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

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

Annapolis
With a stay at this vacation home in Annapolis (Cape Saint Claire), you'll be within a 15-minute drive of Annapolis City Dock and U.S. Naval Academy.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford
Located in Woolford, this vacation home is in a rural location, within a 10-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground ...
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
A stay at this vacation home places you in the heart of Cambridge, steps from Long Wharf Park and Choptank River Lighthouse.
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Annapolis
With a stay at this vacation home in Annapolis (Cape St. John), you'll be within a 15-minute drive of U.S. Naval Academy and Annapolis City Dock.
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

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

Annapolis
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.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

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

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

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
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

Top trending hotels in St. Michaels

St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundableReserve now, pay when you stay
When you stay at St Michaels Inn in St. Michaels, you'll be in the historical district, within a 5-minute drive of St. Michaels Winery and Chesapeake Bay Maritime ...
St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, steps from Perry Cabin Park and 8 minutes by foot from Higgins Yacht Yard and Marina.
Inn at Perry Cabin
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St, St. Michaels, MD
Fully refundableReserve now, pay when you stay
With a stay at The Wildset in St. Michaels, you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Saint Michaels Town Hall.
The Wildset
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Waterfront Property, kayaks, private dock, near town

Waterfront Property, kayaks, private dock, near town

St. Michaels
When you stay at this vacation home in St. Michaels, you'll be on the waterfront, within a 5-minute drive of Saint Michaels Village and St. Michaels Winery.
Waterfront Property, kayaks, private dock, near town
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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.

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