Shady Side Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
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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.
Top Shady Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
Price was CA $2,781, price is now CA $1,859 per person
CA $1,859
per person
Mar 14 - Mar 20
found 15 hours ago
Roundtrip flight included
Montreal (YMQ) to Washington (DCA)
9/10 Wonderful! (1,084 reviews)
Everyone who worked at the hotel was so nice and so accommodating! We had a great stay!
Reviewed on Feb 8, 2026
Hotel Zena Washington DC
Downtown Washington D.C.
Price was CA $1,880, price is now CA $1,362 per person
CA $1,362
per person
Mar 14 - Mar 20
found 15 hours ago
Roundtrip flight included
Montreal (YMQ) to Washington (DCA)
9/10 Wonderful! (1,349 reviews)
Amazing place. Great people and amazing women power!
Reviewed on Jan 25, 2026
Arlo Washington DC
Northwest
Price was CA $1,669, price is now CA $1,210 per person
CA $1,210
per person
Mar 14 - Mar 20
found 15 hours ago
Roundtrip flight included
Montreal (YMQ) to Washington (DCA)
9.2/10 Wonderful! (1,093 reviews)
The cleanliness, city view, discount, and free breakfast. Staff were pleasant as well.
Reviewed on Feb 1, 2026
Shady Side Hotel Deals
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,883 reviews)
Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!
Reviewed on Jan 31, 2026
DoubleTree by Hilton Hotel Largo/Washington DC
9100 Basil Court Upper Marlboro MD
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Feb 23 to Feb 24
CA $133
CA $151 total
Feb 23 - Feb 24
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
Staff was super friendly and helpful - rooms had good sound proofing. I could hear a party going on while I was in the hallway but didn’t hear it at all in my room. My daughter had a competition the next day so the peace and quiet was important.
Reviewed on Feb 1, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is CA $113 per night from Feb 22 to Feb 23
CA $113
CA $129 total
Feb 22 - Feb 23
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
Stayed here for two nights and had a wonderful experience. The staff was exceptional and truly went above and beyond to make sure everything was perfect. The room was clean, the hotel was quiet, and I felt very comfortable throughout my stay. I would absolutely recommend this hotel to friends and ...
Reviewed on Feb 1, 2026
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.
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
