Destination guide

Book a holiday 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-see attractions in the area. A holiday 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 holiday home and experience everything that makes Shady Side a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 highlights

Exploring the natural landscape of Shady Side

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

  • 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 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 centre. 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.

Where to stay near Shady Side?

Our 2019 accommodation listings offer a large selection of 397 holiday rentals near Shady Side. From 276 Houses to 17 Bungalows, find unique holiday homes for you to enjoy a memorable stay with your family and friends. The best place to stay near Shady Side for a long holiday or a weekend break is on HomeAway.

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

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday rentals for a long holiday or just a weekend break in Shady Side:

  • Hillsmere: 20 holiday homes
  • Epping Forest: 21 holiday homes
  • Winchester-on-the-Severn: 23 holiday homes
  • Bay Ridge: 37 holiday homes
  • Eastport: 152 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday homes available.

Can I rent Houses in Shady Side?

Yes, of course. HomeAway offers 276 Houses in Shady Side. Our other popular types of Shady Side holiday rentals include:

  • Bungalows: 17 holiday houses
  • Cabins: 17 holiday houses
  • Cottages: 17 holiday houses

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

Can I find a holiday accommodation with pool in Shady Side?

Yes, you can select your preferred holiday accommodation with pool among our 75 holiday homes with pool available in Shady Side. Please use our search bar to access the selection of holiday rentals available.