Find the best place to stay — Shady Side

Where to stay around Shady Side?

Our 2018 property listings offer a large selection of 350 vacation rentals near Shady Side. From 242 houses to 26 apartments, 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 HomeAway.

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:

  • Eastport: 160 vacation rentals
  • Historic District: 191 vacation rentals
  • Naval Academy: 196 vacation rentals
  • Oyster Harbor: 15 vacation rentals
  • Bay Ridge: 29 vacation rentals

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

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

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

  • Shadyside Park: 600 vacation rentals
  • Captain Avery Museum: 602 vacation rentals
  • Chesapeake Bay Bridge: 579 vacation rentals
  • Breezy Point Beach: 185 vacation rentals
  • Maryland Quiet Waters Park: 609 vacation rentals

But there are many other points of interest around Shady Side listed on HomeAway 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. HomeAway has 242 houses in Shady Side. Our other popular types of vacation rentals in Shady Side include:

  • Apartments: 26 rentals available
  • Condos: 26 rentals available
  • Townhomes: 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 rentals in Shady Side?

Absolutely, HomeAway has 82 golf rentals in Shady Side. You have also many other possibilities in Shady Side area, including:

  • Downtown rentals: 76 rentals
  • Waterfront rentals: 47 rentals
  • Beach rentals: 22 rentals

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

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

Yes, you can select your preferred vacation rental with pool among our 63 vacation rentals with pool available in Shady Side. Please use our search bar to access the selection of vacation rentals available.

    Choose a Vacation Rental for Your Shady Side Getaway

    The natural parks and surrounding scenery provide a peaceful ambiance to your vacation home in Shady Side. This family-friendly city is known for its shopping, restaurants and museums. The area has so much to see with top attractions like Maryland State House, William Paca House and Six Flags America. A vacation rental can help make your stay complete—many rentals come with a kitchen and laundry facilities.

    Attractions In and Around Shady Side

    Looking for places to see while you're in Shady Side? Some of the area's family-friendly draws for travelers include Six Flags America and Chesapeake Beach Water Park. Visitors searching for nearby cultural experiences can take a trip to William Paca House or spend an enlightening afternoon at Captain Avery Museum or Galesville Heritage Museum. To appreciate the outdoor scene, make time for green spaces such as Shadyside Park, Maryland Quiet Waters Park and Sandy Point State Park. You can take a shopping trip to Annapolis City Dock and Westfield Annapolis Mall. While you're in the area, stop by Maryland State House, Bayside History Museum and Annapolis Maritime Museum. Also a trip to Ballet Theater of Maryland, Maryland Hall for Creative Arts or Hammond-Harwood House might be a nice excursion.