Shady Side Holiday Packages
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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
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
"This property was in a central location to lots of places. I did think there was going to be a larger beach that you could go to within the community, however it was a very enjoyable stay. The hostess was sweet and the house is adorable."
Reviewed on 9 Aug 2026
DoubleTree by Hilton Hotel Annapolis
"I loved the free shuttle within 5 miles. It was so great to be dropped off at my conference downtown and not have to worry about parking. They picked me up within 10-15 minutes anytime I called. The restaurant was nice and the food was very good. I loved the location."
Reviewed on 8 Sept 2026
Crowne Plaza Annapolis by IHG
"I only stayed overnight because we were at the Renaissance fair, it was clean, many places to eat within walking distance is a plus."
Reviewed on 8 Sept 2026
