
Shady Side Vacations from $517
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Shady Side Vacation
Take the stress out of travel planning by booking a Shady Side vacation package. One of the best neighborhoods to base yourself in this vibrant city is Deale Beach, which is good for walking and a lot more. Shadyside Park, Franklin Point State Park and Galesville Heritage Museum are just some of the attractions you'll want to explore during your trip to Shady Side. That dream Shady Side vacation is clicks away. Explore flights, hotels and more on Expedia for an adventure that's tailored to suit your style.
The Latest Shady Side vacation packages

Beacon Hotel & Corporate Quarters
Reviewed on Feb 26, 2026

The Jefferson, Washington, DC
Reviewed on Feb 10, 2026

The Churchill Hotel near Embassy Row
Reviewed on Feb 16, 2026

Pentagon Luxe Apartments
Reviewed on Oct 16, 2025
Discover the most popular places to visit in Shady Side
Shadyside Park
Explore the great outdoors at Shadyside Park, a lovely green space in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
Captain Avery Museum
You can spend time exploring the galleries in Captain Avery Museum in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
Shady Side Hotel Deals

DoubleTree by Hilton Hotel Largo/Washington DC
Could’ve been cleaner. There were roaches in my bathroom and I emailed the hotel about it and sent them pics/videos and they basically said oh well and that the rooms are pre-checked prior to check in. So they not doing anything about it. I also seen a big ass rat roaming on the restaurant patio ...
Reviewed on Mar 3, 2026

Historic Inns of Annapolis
Was at Governor Calvert House. Beautiful historic building that is well maintained. Room was clean and comfortable. Parking is minimal, and valet parking is quite expensive, with "dynamic pricing". Hotel is walking distance to many shops and restaurants. Staff was pleasant and accommodating.
Reviewed on Mar 4, 2026

DoubleTree by Hilton Hotel Annapolis
Rooms need more renovation, door knobs not matching. Wall paper separating in bathroom and by elevators. Toilets are so low to ground.
Reviewed on Mar 3, 2026
Find the Best Shady Side Vacation Packages
Shady Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Baltimore Washington Intl. Thurgood Marshall Airport (BWI) |
Population | 5,800 |
Max Temp Winter | 45ºF |
Max Temp Summer | 85ºF |
Top Sights | Chesapeake Beach Water Park, Matapeake State Park and Bayside History Museum |




















