Shady Side
Travel 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 €95 per night from 27 Sept to 28 Sept
€95
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! (1,133 reviews)
"My check-in went smoothly. I had a young lady assist me, and she was absolutely amazing! She was so sweet, funny, and welcoming. She was even kind enough to offer me two cookies and a bottle of water when I arrived at my room. I believe her name tag said Ms. Betty. She had beautiful red and orange ..."
Reviewed on 27 Aug 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
The price is €134 per night from 27 Sept to 28 Sept
€134
27 Sept - 28 Sept
includes taxes & fees
Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,973 reviews)
"My beef is with cancelation. I had to unexpectedly travel out of the country for a death on the family. So I called to let the hotel I was not coming and asked for a refund, after some discussion the hotel agreed not to charge. A couple days later I got an invoice copy from you guys, telling how ..."
Reviewed on 28 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.
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
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
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! (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 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.
