
Cuddy Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Your Cuddy Vacation
Say farewell to the hassle of planning and hello to a Cuddy vacation package. With everything organized before you leave, you can focus on discovering every inch of this city, starting with Downtown Pittsburgh, which is good for markets, dining and views. Any trip to Cuddy needs a well-crafted itinerary. Fill yours with major attractions like South Hills Village, Pittsburgh Botanic Garden and Printscape Arena at Southpointe. A couple of clicks is all it takes to create the ideal Cuddy vacation on Expedia.
Top Cuddy Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Springhill Suites by Marriott Pittsburgh Mt. Lebanon
Mount Lebanon
per person
Jun. 11 - Jun. 15
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Pittsburgh (PIT)
8.8/10 Excellent! (729 reviews)
Nice little hotel. Just fine for a weekend. Lots of walkable bars and restaurants around.
Reviewed on Mar. 29, 2025



DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Downtown Pittsburgh
per person
Jun. 11 - Jun. 15
found 15 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Pittsburgh (PIT)
8.2/10 Very Good! (1,004 reviews)
Allie the front desk manager was incredibly helpful and accomodated our needs perfectly
Reviewed on Mar. 31, 2025

Holiday Inn Express & Suites Pittsburgh North Shore by IHG
North Shore
per person
Jun. 11 - Jun. 15
found 15 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Pittsburgh (PIT)
8.4/10 Very Good! (1,012 reviews)
Holiday inn was fine, like they all are. Parking situation is horrible.
Reviewed on Apr. 3, 2025
Cuddy Hotel Deals

Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $248 per night from Apr. 7 to Apr. 8
CA $248
CA $283 total
includes taxes & fees
Apr 7 - Apr 8
7.8/10 Good! (2,773 reviews)
"Great location!"
Reviewed on Apr. 2, 2025

Drury Plaza Hotel Pittsburgh Downtown
745 Grant Street, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Apr. 20 to Apr. 21
CA $145
CA $165 total
includes taxes & fees
Apr 20 - Apr 21
9.4/10 Exceptional! (1,749 reviews)
"I loved everything about the property. The front desk was very helpful and nice. Also, great price online for room."
Reviewed on Apr. 1, 2025

Omni William Penn Hotel
530 William Penn Place, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Apr. 20 to Apr. 21
CA $204
CA $232 total
includes taxes & fees
Apr 20 - Apr 21
9/10 Wonderful! (1,406 reviews)
"Good location downtown"
Reviewed on Apr. 5, 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.
Frequently asked questions
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.