Book Holiday Homes in Shady Side

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Featured Holiday Homes in Shady Side

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 Walden Golf Club and Crofton Bowl are located ...
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Tracys Landing
Stay at this vacation home in Anne Arundel County. Enjoy free WiFi, private pools, and a sauna. Popular attractions Upper Yough River and Bayside History Museum ...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
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!
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Freshly renovated 3-story home 1 block from USNA!

Freshly renovated 3-story home 1 block from USNA!

Annapolis
The price is NZ$1,120 per night from 25 Feb to 26 Feb
NZ$1,120
includes taxes & fees
25 Feb - 26 Feb
Stay at this vacation home in Annapolis. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions John Smith House and William Paca House ...
Freshly renovated 3-story home 1 block from USNA!
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Annapolis
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a garden, and patios. Popular attractions Navy-Marine Corps Memorial Stadium ...
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Walk to Lake & Boat Ramp: Central Gem in Annapolis

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Annapolis
Stay at this vacation home in Annapolis. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Sandy Point State Park and Bay Hills Golf ...
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Ellen O. Moyer Nature Park at Back ...
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Walk to Everything House

Walk to Everything House

Saint Michaels
Stay at this vacation home in St. Michaels. Enjoy a garden, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Muskrat Park and Clint ...
Walk to Everything House
Brand New Spacious Luxury Home

Brand New Spacious Luxury Home

Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Spa Creek and Annapolis Landing Marina are ...
Brand New Spacious Luxury Home
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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
534 Holiday Homes
Lowest Price
NZ$167
Highest Price
NZ$1,120
Popular accommodation
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore, Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Freshly renovated 3-story home 1 block from USNA!, Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, Walk to Lake & Boat Ramp: Central Gem in Annapolis, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Walk to Everything House, Brand New Spacious Luxury Home

Top trending hotels in Shady Side

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$167 per night from 2 Mar to 3 Mar
NZ$167
includes taxes & fees
2 Mar - 3 Mar
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
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$345 per night from 2 Mar to 3 Mar
NZ$345
includes taxes & fees
2 Mar - 3 Mar
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
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$302 per night from 16 Mar to 17 Mar
NZ$302
includes taxes & fees
16 Mar - 17 Mar
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
Graduate by Hilton Annapolis
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The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$336 per night from 5 Mar to 6 Mar
NZ$336
includes taxes & fees
5 Mar - 6 Mar
Stay at this 4-star spa hotel in Annapolis. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
The Westin Annapolis
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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.