Cuddy Vacations from $418

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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.
Etage Executive Living

Etage Executive Living

3.5 out of 5
Downtown Pittsburgh
Price was $1,170, price is now $418 per person
$418
per person
Apr 18 - Apr 20
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Pittsburgh (PIT)
9.2/10 Wonderful! (1,483 reviews)
The room was spotless. The whole experience was very nice.

Reviewed on Feb 16, 2026

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 $1,578, price is now $1,063 per person
$1,063
per person
May 1 - May 4
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Staff and amenities were great! We loved our room. However, it looks like there were some drinks left in the mini fridge from the patron before us. Other than this, we had a wonderful stay.

Reviewed on Jan 10, 2026

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

2.5 out of 5
North Shore
Save 100% on your flight
Price was $1,068, price is now $757 per person
$757
per person
May 1 - May 4
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,318 reviews)
Yes everything was great, thank you

Reviewed on Feb 17, 2026

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $635, price is now $452 per person
$452
per person
May 1 - May 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
7.8/10 Good! (203 reviews)
Clean and very cozy

Reviewed on Feb 1, 2026

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $1,124, price is now $840 per person
$840
per person
May 1 - May 4
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Pittsburgh (PIT)
8/10 Very Good! (1,009 reviews)
Service at the front are pretty nice and helpful as well as the servers in the restaurant.

Reviewed on Feb 8, 2026

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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
$107 nightly
The price is $122 total per night from Mar 22 to Mar 23
$122 total
Mar 22 - Mar 23
Total with taxes and fees
8.2/10 Very Good! (3,421 reviews)
Great staff and locations. We stayed in a

Reviewed on Feb 17, 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 $181 total per night from Feb 26 to Feb 27
$181 total
Feb 26 - Feb 27
Total with taxes and fees
9.2/10 Wonderful! (1,939 reviews)
Everything met my expectations

Reviewed on Feb 16, 2026

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 Feb 21 to Feb 22
$136 total
Feb 21 - Feb 22
Total with taxes and fees
8.2/10 Very Good! (1,146 reviews)
The room’s AC didn’t work and it was miserable hot all night. No exhaust fan in the smallest bathroom we have ever seen.

Reviewed on Feb 15, 2026

Pittsburgh Marriott City Center
See all 1,780 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 $418 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.