Discover a selection of 335 vacation rentals in Shady Side, MD that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $77 per night, and condos and houses are popular options for a stay in Shady Side. Either way, you'll find a rental for everyone's needs.
Destination guide

Book a vacation rental for your Shady Side getaway

Enjoy the museums and other features of Shady Side. This city's shopping, restaurants and parks draw many visitors. Maryland State House and William Paca House are just a couple of the must-sees in the area. A vacation rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.


Sightseeing in and around Shady Side

Are you hoping to find attractions to see while you're in town? Venture out of your vacation home and experience everything that makes Shady Side a fun place to get away. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Six Flags America (14.9 mi / 24 km)
  • Chesapeake Beach Water Park (10.2 mi / 16.4 km)
  • U.S. Naval Academy Golf Club (11.2 mi / 18 km)
  • Lake Presidential Golf Club (11.9 mi / 19.2 km)
  • St. Michaels Winery (15.9 mi / 25.7 km)
Natural features

Exploring the natural landscape of Shady Side

Whether you're an adventurous traveler or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Shady Side. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Shadyside Park (0.7 mi / 1.2 km)
  • Maryland Quiet Waters Park (6.9 mi / 11.1 km)
  • Kent Island (12.7 mi / 20.5 km)
  • Sandy Point State Park (13.8 mi / 22.2 km)
  • Allen Pond Park (14.1 mi / 22.7 km)
  • Breezy Point Beach (15.1 mi / 24.4 km)
How to get there

How to get to and around Shady Side

Fly into Fort Meade, MD (FME-Tipton), the closest airport, located 21.9 mi (35.3 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Easton, MD (ESN-Easton - Newnam), which is 24 mi (38.6 km) away.

How many vacation rentals are available around Shady Side, MD?

Our 2020 property listings offer a large selection of 335 vacation rentals around Shady Side. From 51 condo and apartment rentals to 218 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Shady Side?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Shady Side:

  • Historic District: 72 vacation rentals
  • Eastport: 97 vacation rentals
  • Homewood: 37 vacation rentals
  • Murray Hill: 67 vacation rentals
  • West Annapolis: 18 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Shady Side?

Vrbo offers a large selection of vacation rentals near lovely places in Shady Side. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Shadyside Park: 477 vacation rentals
  • Captain Avery Museum: 469 vacation rentals
  • Chesapeake Bay Bridge: 448 vacation rentals
  • Breezy Point Beach: 183 vacation rentals
  • Navy-Marine Corps Memorial Stadium: 502 vacation rentals

But there are many other points of interest around Shady Side listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Condos/Apartments in Shady Side?

Yes, of course. Vrbo has 51 Condos/Apartments in Shady Side. Our other popular types of vacation rentals in Shady Side include:

  • Houses: 218 rentals available
  • Cabins: 19 rentals available
  • Cottages: 19 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Townhouses and more.

Can I find a vacation rental with pool in Shady Side?

Yes, you can select your preferred vacation rental with pool among our 55 vacation rentals with pool available in Shady Side. Please use our search bar to access the selection of vacation rentals available.

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