Where to stay around Shady Side, MD?

Our 2018 property listings offer a large selection of 369 vacation rentals near Shady Side. From 256 houses to 29 townhomes, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Shady Side for a holiday or a weekend are on VRBO.

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:

  • Naval Academy: 198 vacation rentals
  • Eastport: 164 vacation rentals
  • Epping Forest: 20 vacation rentals
  • Bay Ridge: 31 vacation rentals
  • Historic District: 196 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:

  • Captain Avery Museum: 623 vacation rentals
  • Shadyside Park: 620 vacation rentals
  • Breezy Point Beach: 188 vacation rentals
  • Sandy Point State Park: 579 vacation rentals
  • Allen Pond Park: 2,131 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 houses in Shady Side?

Yes, of course. VRBO has 256 houses in Shady Side. Our other popular types of vacation rentals in Shady Side include:

  • Townhomes: 29 rentals available
  • Apartments: 26 rentals available
  • Condos: 24 rentals available

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

Can I rent golf rental rentals in Shady Side?

Absolutely, VRBO has 94 golf rental rentals in Shady Side. You have also many other possibilities in Shady Side area, including:

  • Beachfront rentals: 58 rentals
  • Beach view rentals: 16 rentals
  • Monument view rentals: 4 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with online bookable in Shady Side?

Yes, you can select your prefered vacation rental with online bookable among our 368 vacation rentals with online bookable available in Shady Side. Please use our search bar to access the selection of vacation rentals available.

    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)

    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)