
Shady Side Holiday Packages
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Book your Shady Side holiday
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With Wotif's amazingly competitive prices, you'll be packing your suitcase and soaring through the skies in no time at all.
Shady Side Accommodation
Hoping to stay in the vicinity of Shady Side? You may want to consider Annapolis, as it's the nearest place that has any Wotif-listed properties. If you're into plush bedding and first-rate service, you'll love the Loews Annapolis Hotel (126 West St) and The Westin Annapolis (100 Westgate Cir). If you'd prefer book something more affordable, the Holiday Inn Express & Suites Annapolis (2451 Riva Rd) or the Motel 6 Annapolis (1542 Whitehall Rd) could be right up your alley.
Car Hire in Shady Side
Trying to decide which car hire outlet to pick is really very easy when arriving at Baltimore Washington International Thurgood Marshall Airport. With Hertz just a short walk away from the luggage claim area, you and your squad will be driving off before you know it.
Holidays to Shady Side
Eager to scratch your travel itch in Shady Side? We don't blame you. But before you fly off to this exciting destination, how about we fill you in on the essential details?
If you're arriving here via the city of Davidsonville, Shady Side is 16 kilometres to the southeast. If you're coming in from Annapolis, you'll need to head south for 16 kilometres.
If you've been trying to recall just how many people reside in this part of Western Shore of Maryland but your mind's in packing mode, don't stress — we can help. At the last count, the population was 6 000.
Top Shady Side hotels

Graduate by Hilton Annapolis
The room was clean and comfortable. The hotel was decorated with a fun nautical theme. The location is excellent and close to dining and shopping.
Reviewed on 31 Mar 2026

Historic Inns of Annapolis
The parking valet was wonderful- so easy to park and also gave us recommendations of where to eat! Front desk personnel were also lovely.
Reviewed on 1 Apr 2026

DoubleTree by Hilton Hotel Largo/Washington DC
The management team was horrible. My grandson and i played in the pool ( which was dirty ) with a nerf football alll afternoon with no problems. We attempted to go back around 6pm with the same nerf football and we were told that it wasnt allowed....there was no signs specifically addressing this ...
Reviewed on 31 Mar 2026
