
Shady Side Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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.
Top Shady Side Vacation Deals


Sofitel Washington DC Lafayette Square
Reviewed on Feb 8, 2026

Hotel Zena Washington DC
Reviewed on Jan 25, 2026

Arlo Washington DC
Reviewed on Feb 1, 2026
Shady Side Hotel Deals

Historic Inns of Annapolis
Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!
Reviewed on Jan 31, 2026

DoubleTree by Hilton Hotel Largo/Washington DC
Staff was super friendly and helpful - rooms had good sound proofing. I could hear a party going on while I was in the hallway but didn’t hear it at all in my room. My daughter had a competition the next day so the peace and quiet was important.
Reviewed on Feb 1, 2026

DoubleTree by Hilton Hotel Annapolis
Stayed here for two nights and had a wonderful experience. The staff was exceptional and truly went above and beyond to make sure everything was perfect. The room was clean, the hotel was quiet, and I felt very comfortable throughout my stay. I would absolutely recommend this hotel to friends and ...
Reviewed on Feb 1, 2026
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.








