South Side Ski Vacations

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Flight and Ski hotel deals in South Side

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

CA $985
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.8/10 Excellent! (1,236 reviews)
clean room … nice staff breakfast was ok

Reviewed on Oct 12, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh
CA $1,486
per person
Nov 26 - Nov 29
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
Convenient location

Reviewed on Oct 11, 2026

Fairmont Pittsburgh

Fairmont Pittsburgh

Downtown Pittsburgh
CA $1,839
per person
Nov 26 - Nov 29
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.8/10 Excellent! (1,004 reviews)
Location to downtown and sporting events was excellent.

Reviewed on Oct 12, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh
CA $1,380
per person
Nov 26 - Nov 29
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,673 reviews)
We appreciated the central location of the Joinery and the historic red brick building built in 1924. The area isn’t the liveliest, but it is downtown and a 15-minute walk to the Cultural District and the Sixth Street Bridge. Our room was small, but had most of the amenities, including a big flatscreen TV, coat rack, safe, small fridge, coffee maker with coffee and tea pods, steamer, hair dryer, telephone, toiletries, and in-room temperature control. The towels were fairly soft. The bed was comfortable with a pillowtop mattress and down pillows. Storage space was lacking. The hotel has free wi-fi, a bar, coffee bar, restaurant, paid parking, a small gift shop with Pittsburgh themed gifts, and is pet friendly. The lobby is attractive and features art by Pittsburgh artists, vinyl records, and places to hang out. There’s also a microwave guests can use, small snacks available for purchase, ice machines, and a gym. If you take the stairs, you wind up going through housekeeping and employee areas. The staircases were dirty and smelly, but it felt like they didn’t expect guests to ever take the stairs. No one cleaned our room, which was definitely strange. When we first entered our room, it wasn’t cleaned well. There was a towel on the floor and the headboard was dusty, For the price, I felt they could have been more generous by providing drinking water, pens, a pad of paper, etc. However, you can check your bags in for free. Service was friendly at all times.

Reviewed on Oct 13, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

Downtown Pittsburgh
CA $1,467
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.8/10 Excellent! (271 reviews)
Clean room, good location.

Reviewed on Oct 12, 2026

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3 Night Ski holidays in South Side

Price found within the past 48 hours. Click for updated prices.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh
CA $1,380
per person
Nov 26 - Nov 29
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,673 reviews)
We appreciated the central location of the Joinery and the historic red brick building built in 1924. The area isn’t the liveliest, but it is downtown and a 15-minute walk to the Cultural District and the Sixth Street Bridge. Our room was small, but had most of the amenities, including a big flatscreen TV, coat rack, safe, small fridge, coffee maker with coffee and tea pods, steamer, hair dryer, telephone, toiletries, and in-room temperature control. The towels were fairly soft. The bed was comfortable with a pillowtop mattress and down pillows. Storage space was lacking. The hotel has free wi-fi, a bar, coffee bar, restaurant, paid parking, a small gift shop with Pittsburgh themed gifts, and is pet friendly. The lobby is attractive and features art by Pittsburgh artists, vinyl records, and places to hang out. There’s also a microwave guests can use, small snacks available for purchase, ice machines, and a gym. If you take the stairs, you wind up going through housekeeping and employee areas. The staircases were dirty and smelly, but it felt like they didn’t expect guests to ever take the stairs. No one cleaned our room, which was definitely strange. When we first entered our room, it wasn’t cleaned well. There was a towel on the floor and the headboard was dusty, For the price, I felt they could have been more generous by providing drinking water, pens, a pad of paper, etc. However, you can check your bags in for free. Service was friendly at all times.

Reviewed on Oct 13, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh
CA $1,486
per person
Nov 26 - Nov 29
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
Convenient location

Reviewed on Oct 11, 2026

Fairmont Pittsburgh

Fairmont Pittsburgh

Downtown Pittsburgh
CA $1,839
per person
Nov 26 - Nov 29
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.8/10 Excellent! (1,004 reviews)
Location to downtown and sporting events was excellent.

Reviewed on Oct 12, 2026

Don't see what you're looking for?
See all available trips from Columbus to South Side
View all trips

4 Night Ski holidays in South Side

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

CA $985
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.8/10 Excellent! (1,236 reviews)
clean room … nice staff breakfast was ok

Reviewed on Oct 12, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

Downtown Pittsburgh
CA $1,467
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.8/10 Excellent! (271 reviews)
Clean room, good location.

Reviewed on Oct 12, 2026

Don't see what you're looking for?
See all available trips from Columbus to South Side
View all trips

Plan the ultimate ski vacation in South Side

What are some benefits when booking ski vacations in South Side?

If you're interested in skiing, there's nothing quite like a ski vacation. These trips are designed to allow you to enjoy being on the slopes and relax in tranquil and convenient accommodations at the end of the day. Amenities on ski trips can be pretty upscale, so it's easy to relax in a hot tub or at a spa in between your skiing excursions. Plus, they can put you right next to the slopes. You'll even find a variety of different vacation types available whether you're looking for family friendly, cheap, or even last minute ski vacations.

How can I book the best ski vacation in South Side?

It is most important to implement the ski filter in your search when trying to find a ski vacation that will make you happy. Using the filter will automatically remove any entries that don't offer the skiing opportunities you want. After that, you'll need to think about what specifically you want from South Side, and think about the time of year that's best to visit.

How can I find cheap ski vacations?

Cheap ski vacations are readily available in South Side with some as cheap as CA $985. You can see the cheapest options by sorting your accommodation choices by price, which automatically puts the least-expensive results at the top of the list. You may also want to consider an accommodation with a kitchen, so you can cook instead of eating out.

Can I book ski packages?

Yes, ski packages are readily available throughout South Side. All you have to do is put in your travel dates and see what's available. When you book a ski package, you may be able to enjoy discounts with savings of up to 12 when you book your accommodation and your flight together.

What should I consider when booking family ski vacations?

The key to a successful family ski vacation is ensuring that your family is kept happy and entertained. Consider what your family members are interested in and the kind of vacation they want. If they have little skiing experience, for example, you may want to opt for an accommodation that offers ski lessons or a kid's club. Various slope difficulties may be essential in providing opportunities for everyone at South Side.

Can I book all-inclusive ski vacations in South Side?

Yes, all-inclusive ski trips are available and may be precisely what you're looking for. All you have to do is include the filter for all-inclusive stays, and your search results will only show the accommodations that provide this handy feature that allows you to plan your entire trip to South Side in advance.

What's the best time of year to plan a ski trip?

The apparent answer to when you should plan a ski trip is in winter, but other details are important too. If you book for South Side's high season around January and February, you'll likely find increased prices. It's generally best to opt for the early or late season in December and April, as prices tend not to be quite as high.

How can I find the best deals on ski packages in South Side?

When you're looking for cheap ski vacations, there are a few factors you can take advantage of to help get the best deals. Travelling during the off-season can be cheaper since there's more availability. However, the beginning and end of the season tend to be the most affordable for skiing.

Can I book a ski vacation that's fully refundable?

Being fully refundable is a feature you'll find on several accommodation packages in South Side. You can even search for it explicitly using a filter for full refundability.

Why should I book a ski vacation package with Expedia?

When you book with Expedia, you'll find everything you need for cheap ski vacations, luxury ski vacations and everything in between in one central location. You may even be able to enjoy discounts for booking your accommodation and your flight together with savings of up to 12. With Expedia Rewards, you can earn points towards your next booking.

Things to do

Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers

Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers

CA $28
per traveller
Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers
Picture 4 for Activity Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

CA $41
per adult
86% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

CA $18
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
See all activities in South Side

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.