Holiday Rentals in Shady Side
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Check rental availability in Shady Side
Holiday Rentals in Shady Side

The Cottage

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

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

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

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

The Blue Crab Beach House - Free beach passes

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

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Private Cottage on gated estate

Dollhouse in Central Historic St Michaels

Relax on Kent Island in 3 Bedroom Home w/Waterview

Circa 1700 Chesapeake Colonial home on the National Register.

Cass-N-Reel Luxury Houseboat

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Other types of properties in Shady Side you may be interested in

The Cottage
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.
Top Holiday Rental Destinations
Top 20 Shady Side Hotels
More destinations for you
^Eligibility requirements and conditions apply