Cuddy Vacations from $280

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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.

The Latest Cuddy vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Save 100% on your flight
Price was $408, price is now $280 per person
$280
per person
Mar 6 - Mar 9
found 20 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
8/10 Very Good! (1,003 reviews)
OVERALL, WOULD STAY THERE AGAIN. Clean room, great staff. However, No easy parking. Valet is $32...huh? Probably because they have to go far and wide to park the vehicle since there's no dedicated parking lot. I originally asked for a king/pull out couch bed, and we had to be moved to a two-queen room. OMG the "mattress" on the pull-out was flat with the springs poking out. They really need to go thru all the rooms with pull-out couches and replace them. They did move us without extra cost. Breakfast was good.

Reviewed on Dec 28, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $574, price is now $374 per person
$374
per person
Mar 17 - Mar 21
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
8.4/10 Very Good! (1,385 reviews)
Clean and courteous!!! My room was small but perfect for a solo traveler. Bed was EXCELLENT!!! Very nice bathroom.

Reviewed on Dec 28, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $997, price is now $666 per person
$666
per person
Mar 17 - Mar 21
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Extremely helpful front desk staff facilitated early check in, allowing us to rest prior to event

Reviewed on Dec 27, 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $609, price is now $430 per person
$430
per person
Mar 6 - Mar 9
found 20 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Rooms were great and the location was perfect!

Reviewed on Dec 27, 2025

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $699, price is now $516 per person
$516
per person
Mar 6 - Mar 9
found 20 hours ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
8.8/10 Excellent! (1,002 reviews)
Everyone was very friendly, we loved our first visit to Pittsburgh. I'm going to give our review 5 stars but the only thing I question was 2 out of the 3 nights we stayed our room wasn't cleaned. Not sure if that's normal because we had slept in and left around noon. But in any case it was a fun time.

Reviewed on Dec 3, 2025

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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
$128 nightly
The price is $146 total per night from Dec 29 to Dec 30
$146 total
Dec 29 - Dec 30
Total with taxes and fees
8.2/10 Very Good! (3,302 reviews)
It was a beautiful place to stay with great view of the park and rivers. Room was nice but lacked a coffee maker and microwave which was disappointing and quite shocking, to be honest. The staff were very nice and helpful, especially the bellman and valet drivers. Being unfamiliar with the city we ...

Reviewed on Dec 26, 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
$159 nightly
The price is $181 total per night from Jan 4 to Jan 5
$181 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9/10 Wonderful! (1,859 reviews)
Beautiful

Reviewed on Dec 25, 2025

Omni William Penn Hotel
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
112 Washington Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $136 total per night from Jan 1 to Jan 2
$136 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8/10 Very Good! (1,072 reviews)
No soap

Reviewed on Dec 24, 2025

Pittsburgh Marriott City Center
See all 1,714 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

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Frequently asked questions

How much does a Cuddy vacation package cost?
Offering great value package deals from $280 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.