Shady Side, MD
Travel Guide
Visit Shady Side
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$98 nightly
The price is $111 total per night from Aug 30 to Aug 31
$111 total
Aug 30 - Aug 31
Total with taxes and 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 ...
Historic Inns of Annapolis
58 State Circle Annapolis MD
$129 nightly
The price is $147 total per night from Aug 20 to Aug 21
$147 total
Aug 20 - Aug 21
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! (1,926 reviews)
"clean, extremely helpful staff, exactly as described"
Reviewed on Aug 5, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$118 nightly
The price is $135 total per night from Aug 9 to Aug 10
$135 total
Aug 9 - Aug 10
Total with taxes and fees
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! (1,012 reviews)
"This was an amazing stay! My room got serviced daily while I was out exploring and they kept everything nice and clean! The breakfast add on was so worth it so if you have the option to definitely add it! I had an amazing time and can’t wait to stay again!"
Reviewed on Aug 3, 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! (35 reviews)
"Property was very nice and our dog enjoyed the fenced in back yard. The house was very clean and spotless."
Reviewed on Aug 2, 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 ...
Cute, Cozy 2-bedroom house near Annapolis with water access
Crownsville MD
Stay at this vacation home in Crownsville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Joyces Marina and B&A Trail are located ...
9.6/10 Exceptional! (18 reviews)
"Great stay"
Reviewed on Aug 2, 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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- Visit Davidsonville
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- Visit Baltimore
- Captain Avery Museum
- Shadyside Park
- U.S. Naval Academy
- Sandy Point State Park
- Annapolis City Dock
- Chesapeake Bay
- Chesapeake Bay Bridge
- Navy-Marine Corps Memorial Stadium
- Breezy Point Beach
- Maryland State House
- Westfield Annapolis Mall
- Anne Arundel Medical Center
- Chesapeake Beach Water Park
- St. Michaels Winery
- Northern Chesapeake Bay
- Show Place Arena
- Rod n Reel Charter Fishing
- William Paca House
- Chesapeake Bay Maritime Museum
- Prince George's Stadium
- Bowie State University
- Annapolis Mall Shopping Center
- Prince George's Community College
- Maryland Quiet Waters Park
- Annapolis Harbor Center Shopping Center
- Annapolis Harbour Center
- Annapolis Maritime Museum
