Vacation Homes in Shady Side
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Featured Vacation Homes in Shady Side

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

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital

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

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

Historic Home with Parking Steps From Capital & USNA

Circa 1700 Chesapeake Colonial home on the National Register.

Dollhouse in Central Historic St Michaels

Cozy 2br home w/ parking in downtown Annapolis

Thorneton Point Estate

Peaceful Pet-Friendly Stay - Near USNA and Beaches
Top trending hotels in Shady Side

Lovely bay views with kayaks, bikes, fire pit, crabbing & more
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 | 565 Vacation Homes |
|---|---|
Lowest Price | CA $113 |
Highest Price | CA $716 |
Popular accommodation | Cute, Cozy 2-bedroom house near Annapolis with water access, Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach, Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital, Charming Historic Annapolis Home With Two Off-street Parking Places!, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Historic Home with Parking Steps From Capital & USNA, Circa 1700 Chesapeake Colonial home on the National Register., Dollhouse in Central Historic St Michaels, Cozy 2br home w/ parking in downtown Annapolis, Thorneton Point Estate, Peaceful Pet-Friendly Stay - Near USNA and Beaches, Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore |






