Shady Side
Travel Guide
Visit Shady Side
Historic Inns of Annapolis
58 State Circle Annapolis MD
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! (1,883 reviews)
Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!
Reviewed on Jan 31, 2026
DoubleTree by Hilton Hotel Largo/Washington DC
9100 Basil Court Upper Marlboro MD
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Feb 23 to Feb 24
CA $133
CA $151 total
Feb 23 - Feb 24
includes taxes & fees
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! (1,000 reviews)
Staff was super friendly and helpful - rooms had good sound proofing. I could hear a party going on while I was in the hallway but didn’t hear it at all in my room. My daughter had a competition the next day so the peace and quiet was important.
Reviewed on Feb 1, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is CA $113 per night from Feb 22 to Feb 23
CA $113
CA $129 total
Feb 22 - Feb 23
includes taxes & 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 ...
8.6/10 Excellent! (1,003 reviews)
Stayed here for two nights and had a wonderful experience. The staff was exceptional and truly went above and beyond to make sure everything was perfect. The room was clean, the hotel was quiet, and I felt very comfortable throughout my stay. I would absolutely recommend this hotel to friends and ...
Reviewed on Feb 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.
The Blue Crab Beach House - Free beach passes
North Beach MD
Stay at this vacation home in North Beach. Enjoy free WiFi, a water park, and a garden. Popular attractions Bayside History Museum and Chesapeake Beach Water ...
10/10 Exceptional! (78 reviews)
Everything was fine and comfortable
Reviewed on Dec 27, 2025
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, private pools, and breakfast (surcharge). Our guests praise the pool in our reviews. Popular attractions ...
10/10 Exceptional! (129 reviews)
Great host! Great house!
Reviewed on Jan 2, 2026
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Annapolis MD
Stay at this vacation home in Annapolis. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Ballet Theater of Maryland ...
9.8/10 Exceptional! (37 reviews)
Amazing location and house! Host was so accommodating during upcoming inclement weather. The house was so cozy and decorated beautifully! We wish we could have stayed longer
Reviewed on Jan 25, 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.
