Shadyside Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Shadyside Vacation
With all your travel plans organized before you set off, our Shadyside vacation packages mean you can simply focus on having a good time! One place to consider staying in this vibrant city is Elm Grove, which is great for walking and history. Want to explore your new surroundings? West Virginia Penitentiary, Grand Vue Park and Grave Creek Mound are just three of the top places to visit during your trip to Shadyside. Check out Expedia's wide range of travel options and begin planning your ultimate vacation to Shadyside now.
Top Shadyside Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
CA $880
per person
Nov 13 - Nov 15
found 3 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Pittsburgh (PIT)
8.4/10 Very good! (3,785 reviews)
Perfect location for being in town for a Steelers game. Easy walk or train ride to the stadium. Plenty of places to eat in that area or the strip district.
Reviewed on Sep 4, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
CA $1,694
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Pittsburgh (PIT)
8.6/10 Excellent! (1,635 reviews)
Everything about the hotel was fantastic! 10/10 recommend staying here !
Reviewed on Sep 4, 2026
The Inn on Negley
Shadyside
CA $1,090
per person
Nov 13 - Nov 15
found 3 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Pittsburgh (PIT)
10/10 Exceptional! (221 reviews)
Wonderful small Inn in Pittsburgh. I had previously attended high tea, which was delightful, so decided to stay there for this trip - all the staff were extremely helpful and friendly, and breakfast was delicious! Delightful Inn!
Reviewed on Sep 4, 2026
Ready to book your vacation to Shadyside?
Shadyside Hotel Deals
Wonderful 3-bedroom house with AC in charming Shadyside
Shadyside OH
Wingate by Wyndham St. Clairsville/Wheeling
51130 National Road E St. Clairsville OH
Fully refundableReserve now, pay when you stay
CA $111
CA $126 total
Sep 6 - Sep 7
includes taxes & fees
Microtel Inn & Suites by Wyndham Wheeling at Highlands
85 Fort Henry Rd Triadelphia WV
Fully refundableReserve now, pay when you stay
CA $103
CA $115 total
Sep 6 - Sep 7
includes taxes & fees
9.2/10 Wonderful! (1,105 reviews)
"Great stay and great price"
Reviewed on Sep 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.
Frequently asked questions
How much does a Shadyside vacation package cost?
Offering great value package deals from CA $880 on Expedia, you'll be thrilled with how little a vacation to Shadyside costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Shadyside?
You're likely to find lower rates and greater availability in January, February and March. Explore our cheap Shadyside vacation packages and you could get some great off-season discounts.
How many days is enough for Shadyside?
With a well-planned itinerary, you can easily hit the top Shadyside attractions in a handful of days. But if you'd like to explore off the beaten track or go on day tours, think about booking your Shadyside vacation for longer.
How to find the best Shadyside package deals?
Use Expedia's handy filters to find some fabulous Shadyside package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Shadyside package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Shadyside vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Shadyside vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Shadyside?
Land fantastic discounts by reserving your flights early with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Shadyside adventure.
How to plan a trip to Shadyside?
- Choose when to go: Check your diary and pack your bags. Your favourite time of year and the available activities will also help you decide when to escape to Shadyside.
- Budget wisely: As well as the cost of your stay, you should consider other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected expenses that could arise during your trip to Shadyside.
- Determine how many days away: Start by listing all the activities and sights you'd like to get to in Shadyside. Then, estimate how long you'll need for each, as well as any travel time.
- Combine your airfare and accommodations: After you've nailed down your dates and duration, book the ideal Shadyside vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
