Shady Side Holidays

Name: Graduate by Hilton Annapolis
Price range: AU$250
Rating: 9.2

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence
Better together
Save up to AU$703 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Your Shady Side Holiday

Simplify your travel planning with a Shady Side holiday package. A great neighbourhood to base yourself in this fascinating city is Historic District, which is good for history and plenty more. Make your trip to Shady Side even more enjoyable by including some sightseeing. Triton Beach, Shadyside Park and Smithsonian Environmental Research Centre are some of the popular attractions you'll want to explore. Your ultimate Shady Side holiday is just clicks away. Explore accommodation, flights and more on Expedia for an adventure that's tailored to suit your style.

Shady Side Holiday

Shady Side Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Baltimore Washington Intl. Thurgood Marshall Airport (BWI)
Population	5,800
Max Temp Winter	7ºC
Max Temp Summer	29ºC
Top Sights	Chesapeake Beach Water Park, Bayside History Museum and Thanksgiving Farm Wines

Our pick of the best Shady Side Hotel Deals

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

Fully refundableReserve now, pay when you stay

AU$127

8 Feb - 9 Feb

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

Clean and we moved to a quiet room as well

Reviewed on 8 Jan 2026

DoubleTree by Hilton Hotel Largo/Washington DC

9100 Basil Court Upper Marlboro MD

Fully refundableReserve now, pay when you stay

AU$155

29 Jan - 30 Jan

includes taxes & fees

8/10 Very Good! (1,000 reviews)

Great

Reviewed on 12 Jan 2026

Graduate by Hilton Annapolis

126 West St Annapolis MD

Fully refundableReserve now, pay when you stay

AU$250

25 Jan - 26 Jan

includes taxes & fees

9.2/10 Wonderful! (1,005 reviews)

Pleasant staff. Good location to walk to restaurants, shops.

Reviewed on 30 Dec 2025

See all 1,158 properties in Shady Side

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.