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!
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
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Brand New Spacious Luxury Home
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$154 |
Highest Price | AU$334 |
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, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Brand New Spacious Luxury Home |
Top trending hotels in Shady Side
Crowne Plaza Annapolis, an IHG Hotel
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Graduate by Hilton Annapolis
Historic Inns of Annapolis
More ways to explore Shady Side
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.