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! (39 reviews)
"Great yard for dog to run!"
Reviewed on 27 August 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is AED 305 per night from Sep 27 to Sep 28
AED 305
AED 347 total
27 Sep - 28 Sep
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 ...
8.8/10 Excellent! (1,179 reviews)
"From the check in to the check out this was a great experience. The staff were super friendly and helpful, the room was clean and comfortable and the location was fantastic. Free and ample parking added to the pluses. This hotel is an Annapolis gem and we will definitely be staying there again."
Reviewed on 16 September 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
The price is AED 366 per night from Oct 12 to Oct 13
AED 366
AED 543 total
12 Oct - 13 Oct
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 ...
9/10 Wonderful! (2,002 reviews)
"Very impressed with the staff and all the help they provided for us.....! Cleanliness tops. My only complaint is with the cable TV quality. Very poor picture quality and cumbersome remote. This certainly requires a big upgrade. Also it wasn`t till the second day that I found electric outlets for ..."
Reviewed on 16 September 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.
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! (39 reviews)
"Great yard for dog to run!"
Reviewed on 27 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
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Annapolis City Dock and Bay Ridge Beach are ...
9.6/10 Exceptional! (19 reviews)
"We had a lovely stay at this charming cottage on the bay. Everything was well maintained, the host provided strong communication, the grounds are beautiful, and our family found the hot tub to be a wonderful place to both relax amidst nature and reconnect . Also our 2 little dogs felt very much at ..."
Reviewed on 3 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.
