Holiday Rentals in Shady Side
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Holiday Rentals in Shady Side

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

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

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

Floating 2 bed 2 bath condo stunning views of the bay

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

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Cass-N-Reel Luxury Houseboat

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

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

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Luxury Waterfront Executive Family Home Annapolis with All Amenities

Waterfront Getaway, Dock Your Boat & Play!

Edgewater/Mayo Gateaway w/ Hot Tub

Million Dollar View of the Chesapeake Bay

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .
Other types of properties in Shady Side you may be interested in

DoubleTree by Hilton Hotel Largo/Washington DC
Holiday Accommodation Shady Side
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Shady Side are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Shady Side itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Shady Side holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Shady Side, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Shady Side with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
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Top 20 Shady Side Hotels
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