Shady Side Vacations from $195
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Your Shady Side Vacation
Take the stress out of travel planning by booking a Shady Side vacation package. One of the best neighborhoods 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 vacation is clicks away. Explore flights, hotels and more on Expedia for an adventure that's tailored to suit your style.
The Latest Shady Side vacation packages
Price found within the past 48 hours. Click for updated prices.
The Churchill Hotel near Embassy Row
Northwest
Save 100% on your flight
Price was $278, price is now $195 per person
$195
per person
Feb 13 - Feb 15
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,915 reviews)
Restaurant was closed the night of our stay which was disappointing. I also had to pay $70 for “valet” which was just us parking our car in the front and it was never moved so we paid $70 just to have our car sit on the property.
Reviewed on Jan 5, 2026
SIXTY DC
Downtown Washington D.C.
Save 100% on your flight
Price was $833, price is now $501 per person
$501
per person
Feb 14 - Feb 20
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (76 reviews)
Absolutely LOVED the stay!! Johnny was amazing forgot her name but the head of house keeping was amazing!! Best New Years yet!! Planning on coming back for a staycation with the wife where we can just unplug and relax. Just an overall amazing experience.
Reviewed on Jan 6, 2026
Kellogg Conference Hotel at Gallaudet University
Northeast
Save 100% on your flight
Price was $357, price is now $216 per person
$216
per person
Feb 26 - Mar 1
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.2/10 Very Good! (1,002 reviews)
Staff is great. We love this hotel because it has plenty of self parking, so not having to wait for the valet to get your car every time saves a ton of time. The hotel is within the Gallaudet campus which is beautiful and feels very safe. The only issue we had were with the room itself. The furniture and fixtures are a bit dated/worn, though the beds are very comfortable. The sink drain was frozen in the bathroom, the toilet flusher was stuck. We managed to get around these things since we were only there one night and it would not deter us from coming again.
Reviewed on Dec 11, 2025
Discover the most popular places to visit in Shady Side
Shadyside Park
Explore the great outdoors at Shadyside Park, a lovely green space in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
Captain Avery Museum
You can spend time exploring the galleries in Captain Avery Museum in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.
Shady Side Hotel Deals
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $85 total per night from Feb 8 to Feb 9
$85 total
Feb 8 - Feb 9
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Staff was amazing!!! The place was clean!!! Bathroom was out dated and had a couple holes in the ceiling by the fan. Pillows were tiny, that was probably my biggest issue. Had a restaurant inside, didn’t stop in during the evening. Had breakfast, price was reasonable. Got the buffet, food was ...
Reviewed on Jan 6, 2026
DoubleTree by Hilton Hotel Largo/Washington DC
9100 Basil Court Upper Marlboro MD
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $104 total per night from Jan 21 to Jan 22
$104 total
Jan 21 - Jan 22
Total with taxes and fees
8/10 Very Good! (1,005 reviews)
Yes
Reviewed on Dec 30, 2025
Graduate by Hilton Annapolis
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $167 total per night from Jan 15 to Jan 16
$167 total
Jan 15 - Jan 16
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
Pleasant staff. Good location to walk to restaurants, shops.
Reviewed on Dec 30, 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.
Find the Best Shady Side Vacation Packages
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 | 45ºF |
Max Temp Summer | 85ºF |
Top Sights | Chesapeake Beach Water Park, Matapeake State Park and Bayside History Museum |
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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
