Shady Side vacation rentals
Find spaces that suit your style
Find the best place to stay - Shady Side
"PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
Top rated rentals - Shady Side
Photo gallery for Fantastic Location In DTA with its own Parking!
Wedding visit
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Choose a vacation rental for your Shady Side getaway
Enjoy the museums and other features of Shady Side. Renowned for its shopping, restaurants and parks, this city welcomes all visitors. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.
Sightseeing in and around Shady Side
Are you hoping to find top things to see and do while you're in town? Venture out of your vacation home and check out everything that makes Shady Side a fun place to get away. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:
- Thurgood Marshall Memorial (9.5 mi / 15.4 km)
- Chesapeake Beach Water Park (10.4 mi / 16.8 km)
- Six Flags America (14.9 mi / 24 km)
- St. Michaels Winery (16.2 mi / 26 km)
- South River Golf Links (6.3 mi / 10.1 km)
- Renditions Golf Club (9.7 mi / 15.6 km)
Exploring the natural landscape of Shady Side
Whether you're an outdoor enthusiast 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 most enchanting sights, all within 30 miles (48.2 km) of the city center:
- Maryland Quiet Waters Park (7.1 mi / 11.4 km)
- Sandy Point Beach (13.3 mi / 21.4 km)
- Allen Pond Park (13.6 mi / 21.8 km)
- Sandy Point State Park (13.6 mi / 21.9 km)
- Breezy Point Beach (15.3 mi / 24.6 km)
- Patuxent River (25.4 mi / 40.8 km)
Transportation options to and around Shady Side
Fly into Fort Meade, MD (FME-Tipton), the closest airport, located 21.6 mi (34.8 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into College Park, MD (CGS), which is 24.1 mi (38.7 km) away.