Book Holiday Homes in Shady Side
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Shady Side

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Luxury Waterfront Executive Family Home Annapolis with All Amenities

3-bedroom house in Gambrills, in the area of Annapolis, Baltimore, & DC.

Charming Historic Townhouse Steps From USNA

Large 2 bedroom house with private parking in a nice neighborhood

Riverfront Retreat 7mil from MD Renaissance Fest!

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

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Cozy Home in Beautiful 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 | 645 Holiday Homes |
---|---|
Lowest Price | AU$131 |
Highest Price | AU$508 |
Popular accommodation | Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Luxury Waterfront Executive Family Home Annapolis with All Amenities, 3-bedroom house in Gambrills, in the area of Annapolis, Baltimore, & DC., Charming Historic Townhouse Steps From USNA, Large 2 bedroom house with private parking in a nice neighborhood, Riverfront Retreat 7mil from MD Renaissance Fest!, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , RANCH AT ROYAL OAK- Exclusive waterfront pool pier, Cozy Home in Beautiful Annapolis |
Top trending hotels in Shady Side

DoubleTree by Hilton Hotel Largo/Washington DC

Historic Inns of Annapolis

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

Comfort Inn Largo-Washington DC East
More ways to explore Shady Side
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.