Cuddy Vacations from $820

Book a Hotel + Flight or Car together to unlock savings

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.

The Latest Cuddy vacation packages

Price found within the past 48 hours. Click for updated prices.
Downtown Apt Walk to PPG Conv Center More

Downtown Apt Walk to PPG Conv Center More

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,075, price is now $820 per person
$820
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
No reviews
Melwood Suites Unit 103 Studio

Melwood Suites Unit 103 Studio

2 out of 5
Oakland
Save 100% on your flight
Price was $3,498, price is now $2,591 per person
$2,591
per person
Apr 22 - Apr 26
found 11 hours ago
Roundtrip flight included
New York (LGA) to Pittsburgh (PIT)
8/10 Very Good! (2 reviews)
I actually got the "suite" for a family member and his sons. Unfortunately, the pre-teens became mischievous after my family member fell asleep (after a long funeral service). Security called and texted me several times to let me know about their misbehavior. I understood. What I did not appreciate was the tenor of the persons tone as he threatened a few times to "call the cops," even after I assured him that I had reached my family member. His manner was mean-spirited and ominous. Then again, I suppose he had a right to be, considering the children's behavior and the insensitivity to other tenants. I would not payback a steep price for the accommodations again, nor would I recommend it to others.

Reviewed on Sep 28, 2025

City Views Downtown Apt Walk Everywhere

City Views Downtown Apt Walk Everywhere

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,350, price is now $1,017 per person
$1,017
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
No reviews
City Sights 2 Queen Beds Downtown Apt

City Sights 2 Queen Beds Downtown Apt

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $3,962, price is now $3,054 per person
$3,054
per person
Apr 22 - Apr 26
found 11 hours ago
Roundtrip flight included
New York (LGA) to Pittsburgh (PIT)
6/10 (1 review)
Don't see what you're looking for?
See all available trips from Columbus to Cuddy
View all trips

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

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
$125 nightly
The price is $143 total per night from Feb 16 to Feb 17
$143 total
Feb 16 - Feb 17
Total with taxes and fees
8.2/10 Very Good! (3,405 reviews)
Nice

Reviewed on Feb 10, 2026

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
$159 nightly
The price is $182 total per night from Feb 18 to Feb 19
$182 total
Feb 18 - Feb 19
Total with taxes and fees
9/10 Wonderful! (1,937 reviews)
Stayed here multiple times and never disappointed. Clean, safe, and great staff.

Reviewed on Feb 7, 2026

Omni William Penn Hotel
La Quinta Inn by Wyndham Pittsburgh Airport

La Quinta Inn by Wyndham Pittsburgh Airport

3 out of 5
8507 University Blvd Coraopolis PA
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $70 total per night from Feb 22 to Feb 23
$70 total
Feb 22 - Feb 23
Total with taxes and fees
8/10 Very Good! (2,227 reviews)
Everything was great except we never got our wake up call

Reviewed on Feb 10, 2026

La Quinta Inn by Wyndham Pittsburgh Airport
See all 1,774 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.

Find the Best Cuddy Vacation Packages

Cuddy Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Pittsburgh Intl. Airport (PIT)
Top Sights
Andy Warhol Museum, Point State Park and Sandcastle Water Park

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Cuddy vacation package cost?
Offering great value package deals from $820 on Expedia, you'll be surprised at how little a vacation to Cuddy costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Cuddy?
December, January and February are great times to look for cheap Cuddy vacation packages. Opting to travel in less busy periods means you can typically find better prices on flights and accommodations.
How many days is enough for Cuddy?
The ideal duration of your Cuddy vacation depends on what you'd like to do and see. Generally, a few days to a week will give you time to tick off all the top sights and explore some hidden treasures along the way.
How to find the best Cuddy package deals?
Use Expedia's filters to find some great Cuddy package deals. When you begin your search, just 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 browse for Cuddy package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Cuddy vacation as a package?
You can enjoy significant savings on your Cuddy escape by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Cuddy?
If you're planning a spur-of-the-moment Cuddy vacation, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Cuddy vacation packages?
If you're anything like us, you love discovering new places but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Cuddy vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.