Book Holiday Homes in Shady Side

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Featured Holiday Homes in Shady Side

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

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

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.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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
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!
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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, within a 5-minute drive of Walden Golf Club and Regal Waugh Chapel.
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Harbor.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Charming townhome with AC and WiFi in delightful Annapolis

Charming townhome with AC and WiFi in delightful Annapolis

Annapolis
The price is AU$318 per night from 8 Sept to 9 Sept
AU$318
8 Sept - 9 Sept
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of Annapolis City Dock and U.S. Naval Academy.
Charming townhome with AC and WiFi in delightful Annapolis
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 out of 5
Annapolis
With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and People's Brewer Hill ...
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Heated pool, sandy beach, pier, and playground set punch point apart!

Heated pool, sandy beach, pier, and playground set punch point apart!

Sherwood
Located in Sherwood, this vacation home is on the waterfront, a 3-minute drive from Goat Island and 7 minutes from Back Creek Community Park.
Heated pool, sandy beach, pier, and playground set punch point apart!
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

St. Michaels
When you stay at this vacation home in St. Michaels, you'll be on the waterfront, within a 5-minute drive of Perry Cabin Park and Saint Michaels Town Hall.
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
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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
643 Holiday Homes
Lowest Price
AU$271
Highest Price
AU$318
Popular accommodation
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Charming Historic Townhouse Steps From USNA, 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, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, Charming townhome with AC and WiFi in delightful Annapolis, Charming Downtown Annapolis. Stroll to all the Historic District has to offer. , Heated pool, sandy beach, pier, and playground set punch point apart!, Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Top trending hotels in Shady Side

Bay views with kayaks, bikes, fire pit, crabbing and more

Bay views with kayaks, bikes, fire pit, crabbing and more

Shady Side
With a stay at this vacation home in Shady Side, you'll be within a 5-minute drive of Shadyside Park and Captain Avery Museum.
Bay views with kayaks, bikes, fire pit, crabbing and more
Calloway Drive Retreat | House in Shady Side

Calloway Drive Retreat | House in Shady Side

Shady Side
When you stay at this vacation home in Shady Side, you'll be near the beach and 5 minutes by car from Franklin Point State Park.
Calloway Drive Retreat | House in Shady Side
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
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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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$271 per night from 17 Aug to 18 Aug
AU$271
17 Aug - 18 Aug
includes taxes & fees
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
View all properties
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.