Shady Side Holidays

Name: Historic Inns of Annapolis
Price range: AU$290
Rating: 9

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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 Largo/Washington DC

9100 Basil Court Upper Marlboro MD

Fully refundableReserve now, pay when you stay

AU$167

17 May - 18 May

includes taxes & fees

8.2/10 Very Good! (1,003 reviews)

Very clean breakfast was wonderful. Staff was very nice.

Reviewed on 17 Apr 2026

Graduate by Hilton Annapolis

126 West St Annapolis MD

Fully refundableReserve now, pay when you stay

AU$292

10 May - 11 May

includes taxes & fees

9.4/10 Exceptional! (1,013 reviews)

Outstanding

Reviewed on 11 Apr 2026

Historic Inns of Annapolis

58 State Circle Annapolis MD

Fully refundableReserve now, pay when you stay

AU$290

19 Apr - 20 Apr

includes taxes & fees

9/10 Wonderful! (1,844 reviews)

Room was clean, but never cleaned during my stay. Staff was polite and helpful. Parking and check in was most inconvenient. Going from one location to another was not what I expected.

Reviewed on 16 Apr 2026

See all 1,185 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.