Cuddy Vacation Packages

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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.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was CA $1,762, price is now CA $1,315 per person
CA $1,315
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
7.8/10 Good! (169 reviews)
Very nice building: apartment needed TLC but all & all nice stay!

Reviewed on Aug. 10, 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $3,182, price is now CA $2,077 per person
CA $2,077
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
7.6/10 Good! (16 reviews)
Highly recommend! The property was great - with the stunning lobby, fast elevators, and clean, bright unit. Check was not required (after completing the online process & getting my code). The fully furnished apartment with lots of kitchen appliances & coffee! Bed was firm & comfortable, shower was hot with lots of pressure. It even had a washer/dryer. Great location - near restaurants & it really felt like it was connected to the city. Everyone (desk clerk, valet & manager) was friendly & helpful. Finding the parking was a challenge - I suggest calling ahead for directions to the garage.

Reviewed on Aug. 23, 2025

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Price was CA $3,668, price is now CA $2,611 per person
CA $2,611
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.8/10 Excellent! (1,000 reviews)
Everything was great

Reviewed on Aug. 12, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $2,092, price is now CA $1,509 per person
CA $1,509
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
The property was great the and the sfaff were awesome.

Reviewed on Aug. 17, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was CA $1,837, price is now CA $1,441 per person
CA $1,441
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Pittsburgh (PIT)
8.4/10 Very Good! (1,333 reviews)
My room had a mildewy smell, and wasn’t properly cleaned.

Reviewed on Aug. 22, 2025

Ready to book your vacation to Cuddy?

 

Choose your dates

Cuddy Hotel Deals

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Aug 27 to Aug 28
CA $210
CA $240 total
Aug 27 - Aug 28
includes taxes & fees
8/10 Very Good! (2,959 reviews)
"Hotel was ok. Staff was nice. Hotel needs to be modernized though."

Reviewed on Aug. 22, 2025

Wyndham Grand Pittsburgh Downtown
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
530 William Penn Place, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from Sep 10 to Sep 11
CA $220
CA $251 total
Sep 10 - Sep 11
includes taxes & fees
9/10 Wonderful! (1,611 reviews)
"Mark the bellman was super friendly and the front desk staf was exceptional."

Reviewed on Aug. 22, 2025

Omni William Penn Hotel
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
453 Boulevard of the Allies, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Sep 7 to Sep 8
CA $163
CA $190 total
Sep 7 - Sep 8
includes taxes & fees
8.2/10 Very Good! (1,336 reviews)

Reviewed on Aug. 21, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,634 properties in Cuddy
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Cuddy vacation package cost?
You can snap up a vacation package to this destination from CA $1,315 on Expedia. However, how much your vacation to Cuddy costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Cuddy?
You can generally find reduced prices and better availability in January, February and March. Check out our cheap Cuddy vacation packages and you could land some excellent off-season deals.
How many days is enough for Cuddy?
Allow at least 2 days for your Cuddy vacation if you want to take in everything that makes this place special. Explore popular neighbourhoods, including Upper St. Clair and Heidelberg. Then check out top attractions like Printscape Arena at Southpointe and Southpointe Town Centre. With a well-planned itinerary, you can keep busy with room for some me-time too. Want to venture outside of Cuddy? Consider a day trip or two.
How to find the best Cuddy package deals?
Use Expedia's filters to find some of the best Cuddy package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Cuddy package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Cuddy vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Cuddy vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Cuddy?
If you've got your Cuddy vacation dates locked in, book as early as you can to grab some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Cuddy?

  1. Choose your dates: What you plan to do in Cuddy and your favourite season can help you decide when to get away.
  2. Plan your budget wisely: As well as the cost of your hotel, you should factor in other expenses too. These include flights, food and transportation. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Cuddy.
  3. Work out your trip length: Think about how long you'd like to spend exploring Cuddy. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a tailored Cuddy vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.