Shady Side, MD
Travel Guide
Visit Shady Side
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 Jun 19, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$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 ...
8.8/10 Excellent! (1,081 reviews)
"👍"
Reviewed on Aug 6, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
$132 nightly
The price is $150 total per night from Aug 19 to Aug 20
$150 total
Aug 19 - Aug 20
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! (1,928 reviews)
"Nice very well location"
Reviewed on Aug 6, 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
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- Maryland Quiet Waters Park
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- Annapolis Maritime Museum