Shady Side Travel Guide
Tourist Guide
Visit Shady Side
Bay views with kayaks, bikes, fire pit, crabbing and more
Shady Side
Book a stay at this family-friendly vacation home in Shady Side. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shadyside Park and Captain ...
9.6/10 Exceptional! (21 reviews)
Nice Get Away
"Cute cottage in quiet neighborhood for a get away to the Eastern shore. Description is accurate and Mary was easy to communicate with. We enjoyed our stay."
Reviewed on 22 Jun. 2025
Calloway Drive Retreat | House in Shady Side
Shady Side
Stay at this vacation home in Shady Side. Enjoy a water park, laundry facilities, and patios. Popular attractions Franklin Point State Park and Shadyside Park ...
9.4/10 Exceptional! (3 reviews)
Military Bowl
"Wonderful place"
Reviewed on 29 Dec. 2024
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,826 reviews)
"The staff is on point! It was wonderful so wonderful we already made reservations to go back!"
Reviewed on 11 Aug. 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Bay views with kayaks, bikes, fire pit, crabbing and more
Shady Side
Book a stay at this family-friendly vacation home in Shady Side. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shadyside Park and Captain ...
9.6/10 Exceptional! (21 reviews)
Nice Get Away
"Cute cottage in quiet neighborhood for a get away to the Eastern shore. Description is accurate and Mary was easy to communicate with. We enjoyed our stay."
Reviewed on 22 Jun. 2025
The Cottage
Shady Side
Stay at this vacation home in Shady Side. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shadyside Park and Captain Avery Museum are ...
10/10 Exceptional! (7 reviews)
Short and Sweet Stay
"Great little place to stay. It is out of the way and quiet. My kids enjoyed sleeping upstairs together. Truly, we had everything we needed."
Reviewed on 2 Jul. 2025
Calloway Drive Retreat | House in Shady Side
Shady Side
Stay at this vacation home in Shady Side. Enjoy a water park, laundry facilities, and patios. Popular attractions Franklin Point State Park and Shadyside Park ...
9.4/10 Exceptional! (3 reviews)
Military Bowl
"Wonderful place"
Reviewed on 29 Dec. 2024
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Shadyside Park
Explore the great outdoors at Shadyside Park, a lovely green space in Shady Side. Stroll along the area's waterfront or simply savour its top-notch restaurants.
Captain Avery Museum
You can spend time exploring the galleries in Captain Avery Museum during your trip to Shady Side. Stroll along the area's waterfront or simply savour its top-notch restaurants.