Book Holiday Homes in St. Michaels
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Featured Holiday Homes in St. Michaels

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

The Blue Crab Beach House - Free beach passes

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Modern Waterfront House with Amazing views!

Historic Annapolis Home 1.5 blocks from center of town.

Sweet Bamboo Beach Cottage

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
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 | 723 Holiday Homes |
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Lowest Price | NZ$255 |
Highest Price | NZ$1,019 |
Popular accommodation | Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , The Blue Crab Beach House - Free beach passes , 240' Private Beachfront @Kent Island Love Point - Great for Large Groups, ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Modern Waterfront House with Amazing views!, Historic Annapolis Home 1.5 blocks from center of town., Sweet Bamboo Beach Cottage, Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18., Rockhold Creek Cottage, Water Front, Vacation Home, Docks |
More accommodations in St. Michaels
Top trending hotels in St. Michaels

Inn at Perry Cabin

St Michaels Inn

The Wildset

Parsonage Inn
More ways to explore St. Michaels
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^Subject to availability and chosen travel dates.