Shady Side Holiday Homes
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Featured Holiday Homes in Shady Side

Grace Cottage, St Michaels Walk to everything!

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

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Fabulous 5-bedroom house with AC in charming Annapolis

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Charming Historic Annapolis Home With Two Off-street Parking Places!

Cute, Cozy 2-bedroom house near Annapolis with water access

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
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.
Shady Side Holiday Homes essential information
Accommodation | 570 Holiday Homes |
|---|---|
Lowest Price | NZ$161 |
Highest Price | NZ$947 |
Popular accommodation | Grace Cottage, St Michaels Walk to everything!, Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore, Fabulous 5-bedroom house with AC in charming Annapolis, Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything, Charming Historic Annapolis Home With Two Off-street Parking Places!, Cute, Cozy 2-bedroom house near Annapolis with water access, Lovely bay views with kayaks, bikes, fire pit, crabbing & more, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view, Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, Peaceful Pet-Friendly Stay - Near USNA and Beaches |
Top trending hotels in Shady Side

Lovely bay views with kayaks, bikes, fire pit, crabbing & more
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