Shady Side Travel Guide
Tourist Guide
Visit Shady Side
Historic Inns of Annapolis
58 State Circle Annapolis MD
Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,885 reviews)
Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!
Reviewed on 31 Jan 2026
DoubleTree by Hilton Hotel Largo/Washington DC
9100 Basil Court Upper Marlboro MD
The price is NZ$182 per night from 25 Feb to 26 Feb
NZ$182
25 Feb - 26 Feb
includes taxes & fees
Stay at this business-friendly hotel in Upper Marlboro. Enjoy free parking, breakfast (surcharge) and a 24-hour fitness centre. Popular attractions Northwest ...
8.2/10 Very Good! (1,003 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 1 Feb 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is NZ$156 per night from 22 Feb to 23 Feb
NZ$156
22 Feb - 23 Feb
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.6/10 Excellent! (1,002 reviews)
Room was spotless. Staff was very courteous. Would highly recommended.
Reviewed on 5 Feb 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 holiday home in North Beach. Enjoy free Wi-Fi, 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 27 Dec 2025
Chesapeake Houseboat Getaway on Kent Island, Maryland
Stevensville MD
Stay at this houseboat in Stevensville. Enjoy patios, an in-room coffee maker and in-room fireplaces. Popular attractions Romancoke Wharf County Park and Matapeake ...
9.8/10 Exceptional! (45 reviews)
We had the best time staying on this houseboat! It was the perfect spot for our girls trip — clean, spacious, and stocked with everything we needed. The amenities were fantastic, and the location couldn’t have been better — close to everything but still peaceful and relaxing on the water. The grill ...
Reviewed on 27 Oct 2025
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Annapolis MD
Stay at this holiday home in Annapolis. Enjoy free Wi-Fi, private pools and breakfast (surcharge). Our guests praise the pool in their reviews. Popular attractions ...
10/10 Exceptional! (129 reviews)
Great host! Great house!
Reviewed on 2 Jan 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 savour its top-notch restaurants.
Captain Avery Museum
You can spend time exploring the galleries in Captain Avery Museum during your trip to Shady Side. Stroll along the area's waterfront or simply savour its top-notch restaurants.
