Shady Side, MD
Travel Guide
Visit Shady Side
DoubleTree by Hilton Hotel Largo/Washington DC
9100 Basil Court Upper Marlboro MD
Book a stay at this business-friendly hotel in Upper Marlboro. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Northwest ...
8.2/10 Very Good! (1,008 reviews)
Friendly staff. Quiet. Clean. Great area!
Reviewed on 23 Mar, 2026
Graduate by Hilton Annapolis
126 West St Annapolis MD
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 ...
9.4/10 Exceptional! (1,001 reviews)
The toilet ran every few minutes. Some of the carpet as we entered the room was worn away.
Reviewed on 22 Mar, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,004 reviews)
It was OK. Staff in general were not friendly or informative. The breakfast staff were very friendly and helpful. The pool is half the size it seems from the site. Great gym. Nothing was mentioned about the hot tub being out or the loud events that would be taking place that evening. It is a party ...
Reviewed on 23 Mar, 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.
Bay views with kayaks, bikes, fire pit, crabbing and 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 ...
Chesapeake Houseboat Getaway on Kent Island, Maryland
Stevensville MD
Stay at this houseboat in Stevensville. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Romancoke Wharf County Park and Matapeake ...
9.8/10 Exceptional! (49 reviews)
This was a terrific experience. The house boat was extremely clean and well taken care of. The host was proactive with terrific communication. She was upfront with the care and expectations of the stay. It was well stocked, perfect for cooking and enjoying the views from the boat. We are already ...
Reviewed on 11 Mar, 2026
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Saint Michaels MD
Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and patios. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina are ...
9.8/10 Exceptional! (198 reviews)
We had a wonderful time and really enjoyed the back screened in porch which is where we spent a lot of time with our two little dogs.
Reviewed on 12 Mar, 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.
Popular places to visit
Shadyside Park
Explore the great outdoors at Shadyside Park, a lovely green space in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
Captain Avery Museum
You can spend time exploring the galleries in Captain Avery Museum in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
- Shadyside Park
- Captain Avery Museum
- U.S. Naval Academy
- Chesapeake Bay
- Annapolis City Dock
- Chesapeake Bay Bridge
- Sandy Point State Park
- Westfield Annapolis Mall
- Show Place Arena
- Maryland State House
- Bowie State University
- Anne Arundel Medical Center
- Chesapeake Bay Maritime Museum
- Navy-Marine Corps Memorial Stadium
- Annapolis Mall Shopping Center
- St. Michaels Winery
- Annapolis Harbor Center Shopping Center
- Breezy Point Beach
- Maryland Quiet Waters Park
- Annapolis Maritime Museum
- Maryland Hall for Creative Arts
- William Paca House
- Prince George's Community College
- Rod n Reel Charter Fishing
- Renditions Golf Club
- Northern Chesapeake Bay
- Chesapeake Beach Water Park
- Prince George's Stadium