Shady Side Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 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 easyPackages with flights are ATOL protected
Your Shady Side Holiday
Take the stress out of travel planning by booking a Shady Side holiday package. One of the best neighbourhoods 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 holiday is clicks away. Explore flights, hotels and more on Expedia for an adventure that's tailored to suit your style.
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 | 7ºC |
Max Temp Summer | 29ºC |
Top Sights | Chesapeake Beach Water Park, Matapeake State Park and Triton Beach |
Top hotels in Shady Side
Historic Inns of Annapolis
"I loved the building. It’s in a lovely spot a block from the bay so shops and restaurants are right out the front door. The building I stayed in was terrific. The only bummer, was my room was quite small, so I would advise not staying in room 1408. It was the smallest room I’ve ever stayed in. I ..."
Reviewed on 29 Jun 2026
DoubleTree by Hilton Hotel Annapolis
"Excellent value for the Annapolis area. Everything was Good or Very Good and the price was quite reasonable compared to other similar properties."
Reviewed on 29 Jun 2026
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
"The breakfast was cold right after they opened for breakfast. The staff was not friendly"
Reviewed on 29 Jun 2026
Stay near popular Shady Side attractions
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
