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!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Calloway Drive Retreat | House in Shady Side
Dollhouse in Central Historic St Michaels
Private Waterfront Woods | Dock, Kayaks, Views
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Waterfront family resort Lodge with private pier, game room and bar
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
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 | 581 Holiday Homes |
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Lowest Price | NZ$166 |
Highest Price | NZ$781 |
Popular accommodation | Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Calloway Drive Retreat | House in Shady Side, Dollhouse in Central Historic St Michaels, Private Waterfront Woods | Dock, Kayaks, Views, Charming garden row home, easy 4 block walk to the heart of Annapolis., Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, Waterfront family resort Lodge with private pier, game room and bar, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA |
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
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.