Shady Side, MD
Travel Guide
Visit Shady Side
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! (38 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 9 August 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
The price is AED 389 per night from Sep 27 to Sep 28
AED 389
AED 569 total
27 Sep - 28 Sep
includes taxes & fees
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 ...
Graduate by Hilton Annapolis
126 West St Annapolis MD
The price is AED 562 per night from Sep 13 to Sep 14
AED 562
AED 641 total
13 Sep - 14 Sep
includes taxes & fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
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.
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! (38 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 9 August 2026
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 19 June 2026
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Annapolis MD
Stay at this vacation home in Annapolis. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Sandy Point State Park and Annapolis City ...
9.8/10 Exceptional! (52 reviews)
"Great spot for extended family to get together and very convenient to downtown Annapolis. Very cute neighborhood and kids could walk to the nearby shopping center for ice cream. Rooms are lovely - everything is new and nice."
Reviewed on 11 August 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.
