Book Holiday Homes in Shady Side
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Featured Holiday Homes in Shady Side

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

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

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

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
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 | 659 Holiday Homes |
---|---|
Lowest Price | AU$151 |
Highest Price | AU$613 |
Popular accommodation | Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore, 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, Rockhold Creek Cottage, Water Front, Vacation Home, Docks |
Top trending hotels in Shady Side

The Cottage

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

Historic Inns of Annapolis

DoubleTree by Hilton Hotel Largo/Washington DC
More ways to explore Shady Side
Top picks
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^Subject to availability and chosen travel dates.