Book Holiday Homes in Shady Side
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Featured Holiday Homes in Shady Side
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Large 2 bedroom house with private parking in a nice neighborhood
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Location is perfect and a big bonus we have our own parking at the home!
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Shady Side 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 Shady Side vacation homes are the perfect way for you to wing it.
Holiday houses in Shady Side 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 Shady Side 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 Shady Side adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Shady Side 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 Shady Side 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.
Shady Side Holiday Homes essential information
Accommodation | 591 Holiday Homes |
|---|---|
Lowest Price | AU$129 |
Highest Price | AU$1,996 |
Popular accommodation | Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Large 2 bedroom house with private parking in a nice neighborhood, The Cozy Crab- Your Charming Haven in Lovely North Beach!, Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, Charming garden row home, easy 4 block walk to the heart of Annapolis., Location is perfect and a big bonus we have our own parking at the home!, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore |
Top picks
Top trending hotels in Shady Side
Historic Inns of Annapolis
DoubleTree by Hilton Hotel Largo/Washington DC
DoubleTree by Hilton Hotel Annapolis
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
More ways to explore Shady Side
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^Subject to availability and chosen travel dates.