Shady Side, MD
Travel Guide
Visit Shady Side
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
Shady Side MD
Stay at this vacation home in Shady Side. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Franklin Point State Park ...
9.4/10 Exceptional! (8 reviews)
Beautiful Cottage
"We stayed here while my son went to summer camp at USNA and enjoyed the peaceful neighborhood. A couple hiccups occurred at the beginning of the trip but Charles was very open to resolving them with open and timely communication. The kids LOVED having the bikes to ride around the neighborhood and ..."
Reviewed on Jun 19, 2026
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Shady Side MD
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! (37 reviews)
"This property was in a central location to lots of places. I did think there was going to be a larger beach that you could go to within the community, however it was a very enjoyable stay. The hostess was sweet and the house is adorable."
Reviewed on Aug 9, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is ￥15,561 per night from Aug 30 to Aug 31
￥15,561
￥17,738 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
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.
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
Shady Side MD
Stay at this vacation home in Shady Side. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Franklin Point State Park ...
9.4/10 Exceptional! (8 reviews)
Beautiful Cottage
"We stayed here while my son went to summer camp at USNA and enjoyed the peaceful neighborhood. A couple hiccups occurred at the beginning of the trip but Charles was very open to resolving them with open and timely communication. The kids LOVED having the bikes to ride around the neighborhood and ..."
Reviewed on Jun 19, 2026
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Shady Side MD
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! (37 reviews)
"This property was in a central location to lots of places. I did think there was going to be a larger beach that you could go to within the community, however it was a very enjoyable stay. The hostess was sweet and the house is adorable."
Reviewed on Aug 9, 2026
Cute, Cozy 2-bedroom house near Annapolis with water access
Crownsville MD
Stay at this vacation home in Crownsville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Joyces Marina and B&A Trail are located ...
9.6/10 Exceptional! (19 reviews)
"Great stay"
Reviewed on Aug 2, 2026
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.
