Shady Side Travel Guide
Tourist Guide
Visit Shady Side
Lovely bay views with kayaks, bikes, fire pit, crabbing & 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! (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 Aug 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is £70 per night from 27 Sept to 28 Sept
£70
27 Sept - 28 Sept
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (1,150 reviews)
"Rooms kept very clean and comfortable. Staff excellent, extremely friendly and helpful. Food very good and good portions."
Reviewed on 3 Sept 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
The price is £93 per night from 8 Sept to 9 Sept
£93
8 Sept - 9 Sept
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
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
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! (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 Aug 2026
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
Shady Side MD
Stay at this holiday home in Shady Side. Enjoy patios, cable/satellite TV service and an in-room coffee maker. 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 Jun 2026
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Annapolis MD
Stay at this holiday home in Annapolis. Enjoy a fitness centre, a garden and laundry facilities. Popular attractions Sandy Point State Park and Annapolis City ...
9.8/10 Exceptional! (53 reviews)
"Amazing place, friendly community, excellent crabbing."
Reviewed on 18 Aug 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.
Stay near popular Shady Side attractions
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