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
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
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!
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
This vacation home is 3.1 mi (5 km) from Upper Yough River and 4.8 mi (7.7 km) from Bayside History Museum.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
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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 AU$1,028 per night from 3 Feb to 4 Feb
AU$1,028
includes taxes & fees
3 Feb - 4 Feb
A stay at this vacation home places you in the heart of Annapolis, within a 10-minute walk of U.S. Naval Academy and John Smith 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
With a stay at this vacation home in Annapolis (Admiral Heights), you'll be within a 5-minute drive of U.S. Naval Academy and Navy-Marine Corps Memorial ...
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
With a stay at this vacation home in Annapolis (Cape Saint Claire), you'll be within a 15-minute drive of U.S. Naval Academy and Sandy Point State Park.
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Walk to Everything House

Walk to Everything House

Saint Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and Marina.
Walk to Everything House
Charming Historic Townhouse Steps From USNA

Charming Historic Townhouse Steps From USNA

Annapolis
This vacation home is in the heart of Annapolis, within a 5-minute walk of St. John's College and U.S. Naval Academy.
Charming Historic Townhouse Steps From USNA
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

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

Annapolis
A stay at this vacation home places you in the heart of Annapolis, within a 10-minute walk of U.S. Naval Academy and Ellen O. Moyer Nature Park at Back ...
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
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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
523 Holiday Homes
Lowest Price
AU$153
Highest Price
AU$1,028
Popular accommodation
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, 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, Walk to Everything House, Charming Historic Townhouse Steps From USNA, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

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 AU$153 per night from 30 Jan to 31 Jan
AU$153
includes taxes & fees
30 Jan - 31 Jan
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 FedEx Field and ...
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$278 per night from 4 Feb to 5 Feb
AU$278
includes taxes & fees
4 Feb - 5 Feb
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
Crowne Plaza Annapolis, an IHG Hotel

Crowne Plaza Annapolis, an IHG Hotel

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
The price is AU$189 per night from 1 Feb to 2 Feb
AU$189
includes taxes & fees
1 Feb - 2 Feb
Located in Annapolis, Crowne Plaza Annapolis, an IHG Hotel is a 3-minute walk from Westfield Annapolis Mall and 14 minutes by foot from Anne Arundel Medical ...
Crowne Plaza Annapolis, an IHG Hotel
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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 AU$241 per night from 3 Feb to 4 Feb
AU$241
includes taxes & fees
3 Feb - 4 Feb
With a stay at Graduate by Hilton Annapolis, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Civil Rights ...
Graduate by Hilton Annapolis
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.

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^Subject to availability and chosen travel dates.