
Shady Side Holidays
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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
The price is AU$127 per night from 8 Feb to 9 Feb
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
The price is AU$155 per night from 29 Jan to 30 Jan
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
The price is AU$250 per night from 25 Jan to 26 Jan
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
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.











