Shady Side Travel Guide
Tourist Guide
Visit Shady Side
Bay views with kayaks, bikes, fire pit, crabbing and more
Shady Side, MD
Stay at this family-friendly holiday home in Shady Side. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Shadyside Park and Captain Avery ...
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, MD
Stay at this holiday 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
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Shady Side, MD
The price is £364 per night from 4 Aug to 5 Aug
£364
4 Aug - 5 Aug
includes taxes & fees
Stay at this holiday home in Shady Side. Enjoy laundry facilities and air conditioning. Popular attractions Shadyside Park and Franklin Point State Park are ...
Hidden Treasure
"Stay there while my new home was getting work done, house was clean, perfect size for my family. It’s 50 ft to an ice cream shop and laundry mat. Our hoist even included a gift card to the ice cream shop. Great communication and perfect stay for us, felt like home"
Reviewed on 24 Jun 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, MD
Stay at this family-friendly holiday home in Shady Side. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Shadyside Park and Captain Avery ...
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, MD
Stay at this holiday home in Shady Side. Enjoy free Wi-Fi, laundry facilities and air conditioning. Popular attractions Shadyside Park and Captain Avery Museum ...
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, MD
Stay at this holiday 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.