Shady Side, MD
Travel Guide
Visit Shady Side
Historic Inns of Annapolis
58 State Circle Annapolis MD
$167 nightly
The price is $190 total per night from May 31 to Jun 1
$190 total
May 31 - Jun 1
Total with taxes and 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! (1,846 reviews)
Awesome as usual
Reviewed on May 6, 2026
Comfort Inn Largo-Washington DC East
9421 Largo Drive West Upper Marlboro MD
$89 nightly
The price is $101 total per night from May 25 to May 26
$101 total
May 25 - May 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Upper Marlboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
7.8/10 Good! (548 reviews)
Staff friendly. Bed comfortable. Everything else is what we are paying for.
Reviewed on May 5, 2026
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
55 Hampton Park Blvd Capitol Heights MD
$90 nightly
The price is $102 total per night from May 10 to May 11
$102 total
May 10 - May 11
Total with taxes and fees
Book a stay at this business-friendly hotel in Capitol Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6/10 (2,019 reviews)
The worst breakfast I have ever had at a hotel. The breakfast area was unorganized
Reviewed on May 4, 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 ...
9.8/10 Exceptional! (29 reviews)
Very clean with modern decor. Owners were attentive and gave detailed instructions for check-in and check-out. Plenty of beds and extra sheets, blankets and towels. Large dining table for game nights. Additional game shed/man cave in the back yard. Very nice property in a cute area with views of ...
Reviewed on Apr 3, 2026
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 ...
10/10 Exceptional! (53 reviews)
Absolutely Lovely, Julia was very sweet and the home had everything you could have thought of or forgotten to bring.
Reviewed on Apr 13, 2026
Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman MD
Stay at this cottage in Wittman. Enjoy free WiFi, private pools, and laundry facilities. Our guests praise the property condition in our reviews. Popular attractions ...
9.8/10 Exceptional! (243 reviews)
Delightful, well-kept cottage.
Reviewed on May 1, 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.
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- Shadyside Park
- Captain Avery Museum
- U.S. Naval Academy
- Chesapeake Bay
- Chesapeake Bay Bridge
- Annapolis City Dock
- Sandy Point State Park
- Annapolis Mall Shopping Center
- Westfield Annapolis Mall
- Breezy Point Beach
- Anne Arundel Medical Center
- Show Place Arena
- Navy-Marine Corps Memorial Stadium
- Northern Chesapeake Bay
- Maryland State House
- Bowie State University
- Chesapeake Bay Maritime Museum
- Annapolis Harbor Center Shopping Center
- Prince George's Stadium
- Maryland Quiet Waters Park
- St. Michaels Winery
- William Paca House
- Chesapeake Beach Water Park
- Annapolis Maritime Museum
- Prince George's Community College
- Rod n Reel Charter Fishing
- Renditions Golf Club
