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
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a water park, and patios. Popular attractions John Smith House and Annapolis ...
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
Stay at this vacation home in Crofton. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Crofton Bowl and Bowie Golf and Country Club ...
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
Stay at this vacation home in North Beach. Enjoy free WiFi, a water park, and a garden. Popular attractions Bayside History Museum and Chesapeake Beach Water ...
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
Book a stay at this beach vacation home in Stevensville. Enjoy free WiFi, a beach locale, and private hot tubs. Our guests praise the helpful staff in our reviews. ...
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 NZ$441 per night from 22 Apr to 23 Apr
NZ$441
includes taxes & fees
22 Apr - 23 Apr
Stay at this vacation home in Stevensville. Enjoy free WiFi, a sauna, and a garden. Popular attractions Matapeake State Park and Paul Reed Smith Guitars are ...
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Modern Waterfront House with Amazing views!

Modern Waterfront House with Amazing views!

North Beach
Stay at this vacation home in North Beach. Enjoy a water park, a garden, and patios. Popular attractions 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
Stay at this vacation home in Annapolis. Enjoy free WiFi, patios, and in-room jetted tubs. Popular attractions Ellen O. Moyer Nature Park at Back Creek and Banneker ...
Historic Annapolis Home 1.5 blocks from center of town.
Sweet Bamboo Beach Cottage

Sweet Bamboo Beach Cottage

north beach
Stay at this vacation home in North Beach. Enjoy a beach locale, a water park, and a garden. Popular attractions Bayside History Museum and Chesapeake Beach ...
Sweet Bamboo Beach Cottage
Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Deale
Stay at this vacation home in Deale. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions 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
666 Holiday Homes
Lowest Price
NZ$169
Highest Price
NZ$641
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 NZ$641 per night from 20 Apr to 21 Apr
NZ$641
includes taxes & fees
20 Apr - 21 Apr
Stay at this vacation home in Shady Side. Enjoy free WiFi and air conditioning. Popular attractions Shadyside Park and Captain Avery Museum are located ...
The Cottage
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 NZ$333 per night from 29 Apr to 30 Apr
NZ$333
includes taxes & fees
29 Apr - 30 Apr
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
Historic Inns of Annapolis
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 NZ$171 per night from 29 Apr to 30 Apr
NZ$171
includes taxes & fees
29 Apr - 30 Apr
Book a stay at this business-friendly hotel in Capitol Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
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Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundable
The price is NZ$169 per night from 29 Apr to 30 Apr
NZ$169
includes taxes & fees
29 Apr - 30 Apr
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Country Inn & Suites by Radisson, Annapolis, MD
Don't see what you're looking for?
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.