South Side Ski Vacations
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Top Ski vacation packages in South Side
Price found within the past 48 hours. Click for updated prices.
- Americas Best Value Inn Pittsburgh Airport
Dec 26 - Jan 1Americas Best Value Inn Pittsburgh Airport + Flight
Coraopolis6 nights2.0 star property6.6/10 - (1,001 reviews)"Basically, a place to lay my head take a shower get some coffee and hit the road"Reviewed November 11, 2026Roundtrip • New York (JFK) - Pittsburgh (PIT)JFK - PIT • Nonstop PIT - JFK • Nonstop$594$408found 1 day agoper traveler - DoubleTree by Hilton Washington Meadow Lands Casino Area
Dec 26 - Jan 1DoubleTree by Hilton Washington Meadow Lands Casino Area + Flight
Washington6 nights4.0 star property7.8/10 - Good (987 reviews)Roundtrip • New York (JFK) - Pittsburgh (PIT)JFK - PIT • Nonstop PIT - JFK • Nonstop$857$626found 1 day agoper traveler - Kimpton Hotel Monaco Pittsburgh by IHG
Dec 26 - Jan 1Kimpton Hotel Monaco Pittsburgh by IHG + Flight
Downtown Pittsburgh6 nights4.5 star property9.4/10 - Exceptional (1,313 reviews)"The hotel does not have a lobby as you may be used to large hotels, but if you’re looking for renovated clean room and good food in the local restaurant, this hotel tops others in the neighborhood."Reviewed November 12, 2026Roundtrip • New York (JFK) - Pittsburgh (PIT)JFK - PIT • Nonstop PIT - JFK • Nonstop$1,136$831found 1 day agoper traveler - The Oaklander Hotel, Autograph Collection
Dec 26 - Jan 1The Oaklander Hotel, Autograph Collection + Flight
Oakland6 nights4.5 star property9.2/10 - Wonderful (860 reviews)"The room was enormous with huge window, so lots of light. The bathroom was spacious and modern. Good quality bath products in large containers so no wasteful mini bottles There was lots of closet and storage space. There was a coffee bar in the room and plenty of bottled water. Room also had a generous sized desk."Reviewed November 13, 2026Roundtrip • New York (JFK) - Pittsburgh (PIT)JFK - PIT • Nonstop PIT - JFK • Nonstop$1,077$797found 1 day agoper traveler - Hampton Inn & Suites Pittsburgh-Downtown
Dec 26 - Jan 1Hampton Inn & Suites Pittsburgh-Downtown + Flight
Downtown Pittsburgh6 nights2.5 star property9.4/10 - Exceptional (1,368 reviews)"The staff, on the whole, were lovely"Reviewed November 12, 2026Roundtrip • New York (JFK) - Pittsburgh (PIT)JFK - PIT • Nonstop PIT - JFK • Nonstop$823$616found 1 day agoper traveler
Top Ski South Side Hotels
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG2.5 star property
South Side Flats, 0.7 mi from South Side
8.2 out of 10, Very good, (1,046 reviews)
8.2/10
Very good
(1,046 reviews)
"Plenty of parking, clean room, and good breakfast."
$91 nightly
The price is $104
$104 total
Dec 14 - Dec 15
Total with taxes and fees
SpringHill Suites by Marriott Pittsburgh Southside Works
SpringHill Suites by Marriott Pittsburgh Southside Works3.0 star property
South Side Flats, 0.8 mi from South Side
8.6 out of 10, Excellent, (1,001 reviews)
8.6/10
Excellent
(1,001 reviews)
"The hotel is situated next to train tracks that actually make the building shake slightly when they come by. Every train that came by I heard through the night and I was on the 6th floor. I will not return"
$114 nightly
The price is $129
$129 total
Dec 7 - Dec 8
Total with taxes and fees
HYATT house Pittsburgh-South Side
HYATT house Pittsburgh-South Side3.0 star property
South Side Flats, 0.8 mi from South Side
8.8 out of 10, Excellent, (1,000 reviews)
8.8/10
Excellent
(1,000 reviews)
$134 nightly
The price is $153
$153 total
Nov 16 - Nov 17
Total with taxes and fees
9.6 out of 10, Exceptional, (133 reviews)
9.6/10
Exceptional
(133 reviews)
"Private but not attached bathroom/ shower wad different, but very clean and roomy."
$115 nightly
The price is $131
$131 total
Nov 18 - Nov 19
Total with taxes and fees
2615 Jane Down - Southside
2615 Jane Down - SouthsideSouth Side Flats, 0.4 mi from South Side
8.8 out of 10, Excellent, (5 reviews)
8.8/10
Excellent
(5 reviews)
"Very clean modern place in nice neighborhood. Location great for walking. Found a vegan restaurant less than two blocks away. "
$168 nightly
The price is $190
$190 total
Nov 16 - Nov 17
Total with taxes and fees
The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!
The Speakeasy - Stylish 1-BR w/ Roaring 20s Charm!South Side Flats, 0.3 mi from South Side
7.0 out of 10, Good, (2 reviews)
7.0/10
Good
(2 reviews)
"The location of the property is in the heart of the Southside and walkable to many places (Station Square, over the bridge to downtown, and lots of close places right on Carson St). Street parking is available, but there is not much of it. Our first night we had to pay to park in a public lot just around the corner. The next day I was able to get street parking, and then didn't move my car the rest of the weekend. This is an older apartment and located in a narrow alley. The property was...
Birmingham Bridge Beauty Cozy Stay Near Downtown
Birmingham Bridge Beauty Cozy Stay Near DowntownSouth Side Flats, 0.3 mi from South Side
2.0 out of 10, (1 review)
2.0/10
(1 review)
"While the host was responsive when requested, the check-in link provided with pictures was not live, making check-in confusing especially in the dark when we didn’t know the entrance was on the side of the building. The property is basic with no charm or comfort commodities which are usually found in a rental property such as this. There are two doors from the unit that gain access to other areas of the house that, while are locked to prevent people from gaining access to the apartment, they are...
$151 nightly
The price is $164
$164 total
Nov 15 - Nov 16
Total with taxes and fees
Iron City of South Side Flats Charming 2-bedroom Unit
Iron City of South Side Flats Charming 2-bedroom UnitSouth Side Flats, 0.2 mi from South Side
10.0 out of 10, Exceptional, (14 reviews)
10/10
Exceptional
(14 reviews)
"Overall very nice. Good location, clean, moderately comfortable place. I was not a fan of the beds and bedding as the bed and pillows were too hard for my liking. Otherwise, nice and would recommend."
$230 nightly
The price is $261
$261 total
Nov 16 - Nov 17
Total with taxes and fees
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.
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.
Planning your South Side ski vacation
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 $408. 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 $408. 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.