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

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Historic Annapolis Home 1.5 blocks from center of town.

Sweet Bamboo Beach Cottage

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

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

Walking distance to Navy Stadium! No cleaning fees!

Historic Home with Parking Steps From Capital & USNA

Charming Historic Townhouse Steps From USNA

Historic Downtown House with Off Street Parking
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$173 |
Highest Price | AU$294 |
Popular accommodation | Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything, Historic Annapolis Home 1.5 blocks from center of town., Sweet Bamboo Beach Cottage, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore, Walking distance to Navy Stadium! No cleaning fees!, Historic Home with Parking Steps From Capital & USNA, Charming Historic Townhouse Steps From USNA, Historic Downtown House with Off Street Parking |
Top trending hotels in Shady Side

DoubleTree by Hilton Hotel Largo/Washington DC

Graduate by Hilton Annapolis

Historic Inns of Annapolis

Crowne Plaza Annapolis by IHG
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**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
