Vacation Homes in Shady Side
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Featured Vacation Homes in Shady Side

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

Large 2 bedroom house with private parking in a nice neighborhood

The Cozy Crab- Your Charming Haven in Lovely North Beach!

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

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

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Location is perfect and a big bonus we have our own parking at the home!

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & Parking
Top trending hotels in Shady Side

Historic Inns of Annapolis
Vacation Rentals in Shady Side
What kind of vacation do you want in Shady Side? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Shady Side that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Shady Side, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
Shady Side Vacation Homes essential information
Accommodation | 645 Vacation Homes |
|---|---|
Lowest Price | CA $97 |
Highest Price | CA $1,629 |
Popular accommodation | Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA, Large 2 bedroom house with private parking in a nice neighborhood, The Cozy Crab- Your Charming Haven in Lovely North Beach!, Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, Charming garden row home, easy 4 block walk to the heart of Annapolis., Location is perfect and a big bonus we have our own parking at the home!, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore, 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!, Gather, Relax & Explore — Townhome 1 Block from State Capitol Building with Backyard & Parking, Edgewater/Mayo Gateaway w/ Hot Tub |






