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!

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

Annapolis
A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.
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

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

Crofton
A stay at this vacation home places you in the heart of Crofton, a 1-minute drive from Walden Golf Club and 6 minutes from Bell Branch Big Dog Park.
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach
Located in North Beach, this vacation home is by the sea, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
The Blue Crab Beach House - Free beach passes
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240' Private Beachfront @Kent Island Love Point - Great for Large Groups

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

stevensville
Located in Stevensville, this vacation home is on the waterfront, a 1-minute drive from Love Point State Park and 7 minutes from Paul Reed Smith Guitars.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Stevensville
The price is AU$416 per night from 7 Apr to 8 Apr
AU$416
includes taxes & fees
7 Apr - 8 Apr
Located in Stevensville, this vacation home is a 4-minute drive from Matapeake State Park and 7 minutes from Paul Reed Smith Guitars.
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Modern Waterfront House with Amazing views!

Modern Waterfront House with Amazing views!

North Beach
Located in North Beach, this vacation home is on the waterfront, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
Modern Waterfront House with Amazing views!
Historic Annapolis Home 1.5 blocks from center of town.

Historic Annapolis Home 1.5 blocks from center of town.

Annapolis
A stay at this vacation home places you in the heart of Annapolis, within a 15-minute walk of U.S. Naval Academy and Spa Creek.
Historic Annapolis Home 1.5 blocks from center of town.
Sweet Bamboo Beach Cottage

Sweet Bamboo Beach Cottage

north beach
When you stay at this vacation home in North Beach, you'll be on the beach, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water ...
Sweet Bamboo Beach Cottage
Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Deale
With a stay at this vacation home, you'll be centrally located in Deale, within a 10-minute drive of Upper Yough River and Franklin Point State Park.
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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

The Cottage

Shady Side
The price is AU$613 per night from 5 Apr to 6 Apr
AU$613
includes taxes & fees
5 Apr - 6 Apr
Located in Shady Side, this vacation home is within a 5-minute drive of Shadyside Park and Captain Avery Museum.
The Cottage
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

2.5 out of 5
55 Hampton Park Blvd, Capitol Heights, MD
Fully refundableReserve now, pay when you stay
The price is AU$151 per night from 13 Apr to 14 Apr
AU$151
includes taxes & fees
13 Apr - 14 Apr
Located in Capitol Heights, La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway is connected to a shopping center, a 3-minute drive from Northwest Stadium ...
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$314 per night from 15 Apr to 16 Apr
AU$314
includes taxes & fees
15 Apr - 16 Apr
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Historic Inns of Annapolis
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DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

4 out of 5
9100 Basil Court, Upper Marlboro, MD
Fully refundableReserve now, pay when you stay
The price is AU$206 per night from 20 Apr to 21 Apr
AU$206
includes taxes & fees
20 Apr - 21 Apr
When you stay at DoubleTree by Hilton Hotel Largo/Washington DC in Upper Marlboro, you'll be in the business district, a 4-minute drive from Northwest Stadium ...
DoubleTree by Hilton Hotel Largo/Washington DC
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See all available properties in Shady Side
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.