Shady Side Holidays from £1,142

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Your Shady Side Holiday

Take the stress out of travel planning by booking a Shady Side holiday package. One of the best neighbourhoods to base yourself in this vibrant city is Deale Beach, which is good for walking and a lot more. Shadyside Park, Franklin Point State Park and Galesville Heritage Museum are just some of the attractions you'll want to explore during your trip to Shady Side. That dream Shady Side holiday is clicks away. Explore flights, hotels and more on Expedia for an adventure that's tailored to suit your style.

Top Shady Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Sofitel Washington DC Lafayette Square
Kimpton Hotel Monaco Washington DC by IHG
Eurostars Saint Gregory Dupont Circle Georgetown
Landing at Bridge District
Beacon Hotel & Corporate Quarters

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, Matapeake State Park and Triton Beach

Top hotels in Shady Side

DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

4 out of 5
9100 Basil Court Upper Marlboro MD
The price is £97 per night from 12 Apr to 13 Apr
£97
12 Apr - 13 Apr
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
Clean room. Friendly staff.

Reviewed on 25 Mar 2026

DoubleTree by Hilton Hotel Largo/Washington DC
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is £154 per night from 12 Apr to 13 Apr
£154
12 Apr - 13 Apr
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
Unique hotel in the heart of Annapolis. The room was lovely, comfortable and well equipped. Parking was a bit expensive $32 one day and strange, couldnt actually park in the covered garrage that was only for vallette patrons. Would have been nice to have a regular coffee maker in the room, only instant ...

Reviewed on 27 Mar 2026

Graduate by Hilton Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is £137 per night from 5 Apr to 6 Apr
£137
5 Apr - 6 Apr
includes taxes & fees
9/10 Wonderful! (1,863 reviews)
Clean room, friendly staff, and the PERFECT location for walking downtown Annapolis.

Reviewed on 24 Mar 2026

Historic Inns of Annapolis
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. Flight-inclusive packages are ATOL protected.