South Side Ski Vacations 2026

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Top Ski vacation packages in South Side

Price found within the past 48 hours. Click for updated prices.

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh

$612

per person

Dec 5 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Pittsburgh (PIT)

8.6/10 Excellent! (1,639 reviews)

We took advantage of off-site parking to save but loved the hotel bar and rooftop views. Would definitely stay here again!

Reviewed on Sep 16, 2026

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

$781

per person

Dec 5 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Pittsburgh (PIT)

8.6/10 Excellent! (1,004 reviews)

I would highly recommend! We spent our 2nd anniversary there for the Steelers game and when we arrived to our room they were so kind to leave us some goodies and a little note to congratulate us! It was a very clean hotel and room! Staffing very kind! Will be staying again for sure!

Reviewed on Sep 14, 2026

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

Downtown Pittsburgh

$636

per person

Dec 5 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Pittsburgh (PIT)

8.4/10 Very Good! (1,106 reviews)

The Oaklander Hotel, Autograph Collection

Oakland

$670

per person

Dec 5 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Pittsburgh (PIT)

9.2/10 Wonderful! (826 reviews)

Placemakr Downtown Pittsburgh at The Pennsylvanian

Downtown Pittsburgh

$780

per person

Dec 5 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Pittsburgh (PIT)

8.6/10 Excellent! (228 reviews)

This hotel and suite were spacious and beautiful. It is inside the historic former Union Station, the building is stunning with a grand rotunda entrance, Very unique, We had a one bedroom apartment with a kitchen (full) and laundry in the apartment. It is centrally located downtown, making it easy to get around Pittsburgh. Friendly front desk staff who are super helpful.

Reviewed on Sep 15, 2026

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5* Ski vacations in South Side

Price found within the past 48 hours. Click for updated prices.

Nemacolin

$1,244

per person

Nov 6 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Pittsburgh (PIT)

9.2/10 Wonderful! (487 reviews)

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3 Night Ski vacations in South Side

Price found within the past 48 hours. Click for updated prices.

DoubleTree by Hilton Pittsburgh - Cranberry

$419

per person

Dec 5 - Dec 8

found 20 hours ago

Roundtrip non-stop flight included

Houston (HOU) to Pittsburgh (PIT)

8.8/10 Excellent! (1,000 reviews)

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

$882

per person

Dec 4 - Dec 7

found 16 hours ago

Roundtrip flight included

Dallas (DFW) to Pittsburgh (PIT)

8.6/10 Excellent! (1,004 reviews)

Reviewed on Sep 14, 2026

The Inn on Negley

Shadyside

$728

per person

Oct 31 - Nov 3

found 18 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)

10/10 Exceptional! (221 reviews)

This was the second time that I stayed at The Inn on Negley, and once again it was an incredible experience. The staff were warm and welcoming, with a special shout out to Eva. Her enthusiasm and hospitality was the highlight of our stay, and I can’t thank her enough for everything. We can’t wait to return!

Reviewed on Sep 15, 2026

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4 Night Ski vacations in South Side

Price found within the past 48 hours. Click for updated prices.

Americas Best Value Inn Pittsburgh Airport

$353

per person

Oct 29 - Nov 2

found 9 hours ago

Roundtrip flight included

Houston (IAH) to Pittsburgh (PIT)

6.6/10 (1,002 reviews)

Stay Pittsburgh

Downtown Pittsburgh

Save 100% on your flight

$764

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Houston (HOU) to Pittsburgh (PIT)

8/10 Very Good! (325 reviews)

Good location near a bunch of restaurants that you can walk to. We were in town for the Steelers game and this is a good place to stay for that. Easy to get an Uber/Lyft too if you need one. Apartment was very clean. Queen bed was good. Parking lot $30 per day across street. Would stay here again if in Downtown Pittsburgh area.

Reviewed on Sep 14, 2026

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

Save 100% on your flight

$976

per person

Dec 5 - Dec 9

found 1 day ago

Roundtrip non-stop flight included

Houston (HOU) to Pittsburgh (PIT)

8.6/10 Excellent! (1,004 reviews)

Reviewed on Sep 14, 2026

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What are some things I should consider when booking a South Side ski trip package?

Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in.

How can I find cheap South Side ski packages?

Right now, ski trips start at just $353. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in South Side?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in South Side. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow.

How much does a ski trip to South Side cost?

Sensational ski trips to South Side start from $353. Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply.

When’s the best time of year to plan a ski trip to South Side?

The best time to hit the slopes in South Side depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days.

Can I book South Side ski packages with airfare?

Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly.

Can I book a South Side ski trip with free cancellation and/or flexible dates?

Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options.

Why should I book a ski package in South Side with Expedia?

Simple search and fantastic filters make it easy to find, build, and book your dream South Side ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.