Shady Side holiday rentals
Find spaces that suit your style
Find the best place to stay - Shady Side
"PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Choose a holiday 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 holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.
Sightseeing in and around Shady Side
Do you want to find top things to see and do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Shady Side has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:
- Chesapeake Beach Water Park (10.4 mi / 16.8 km)
- Maryland Renaissance Festival (11.5 mi / 18.6 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 active traveller or just want to spend some time taking in the scenery, Shady Side is a great place to get out in nature. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city centre:
- Maryland Quiet Waters Park (7.1 mi / 11.4 km)
- Matapeake State Park (11.7 mi / 18.8 km)
- Sandy Point Beach (13.3 mi / 21.4 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)
Transport 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 centre. If you're unable to find a flight that fits your schedule, you might consider flying into College Park, MD (CGS), which is 24.1 mi (38.7 km) away.