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 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 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 396 holiday rentals near Shady Side. From 267 Houses to 64 Condos/Apartments, 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 Stayz.

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:

  • Eastport: 155 holiday homes
  • Homewood: 57 holiday homes
  • Historic District: 106 holiday homes
  • Hillsmere: 19 holiday homes
  • Epping Forest: 22 holiday homes

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

What are the most popular points of interest and landmarks to stay near when travelling to Shady Side?

Stayz offers a large selection of holiday homes near great places in Shady Side. From Stayz travellers, the most popular points of interest to stay near are:

  • Shadyside Park: 651 holiday rentals
  • Captain Avery Museum: 651 holiday rentals
  • Fort George G. Meade: 902 holiday rentals
  • Bowie Golf and Country Club: 2,060 holiday rentals
  • U.S. Naval Academy Golf Club: 627 holiday rentals

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

Can I rent Houses in Shady Side?

Yes, of course. Stayz offers 267 Houses in Shady Side. Our other popular types of Shady Side holiday rentals include:

  • Condos/Apartments: 64 holiday houses
  • Cabins: 16 holiday houses
  • Cottages: 16 holiday houses

But you can also enjoy a great stay in one of our other holiday rentals including Bungalows 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 66 holiday homes with pool available in Shady Side. Please use our search bar to access the selection of holiday rentals available.