Book Holiday Homes in Shady Side
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Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Shady Side
Directly Across from Gate One & Steps from the Waterfront
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Bay views with kayaks, bikes, fire pit, crabbing and more
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Recently Renovated Annapolis Home - Conveniently Located
3 Story Stunner in Murray Hill <1 mile from USNA!
Your Annapolis Adventure Starts Here!!
Charming garden row home, easy 4 block walk to the heart of Annapolis.
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 | 527 Holiday Homes |
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Lowest Price | AU$130 |
Highest Price | AU$1,353 |
Popular accommodation | Directly Across from Gate One & Steps from the Waterfront , Rockhold Creek Cottage, Water Front, Vacation Home, Docks, Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore, Bay views with kayaks, bikes, fire pit, crabbing and more, Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Recently Renovated Annapolis Home - Conveniently Located, 3 Story Stunner in Murray Hill <1 mile from USNA!, Your Annapolis Adventure Starts Here!! , Charming garden row home, easy 4 block walk to the heart of Annapolis. |
More accommodations in Shady Side
Top trending hotels in Shady Side
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Historic Inns of Annapolis
Graduate by Hilton Annapolis
Country Inn & Suites by Radisson, Washington, D.C. East - Capitol Heights, MD
More ways to explore Shady Side
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.