Southside Ski Vacations 2026

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Top Ski vacation packages in Southside

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

King’s Creek Resort by Spinnaker

$610

per person

Nov 8 - Nov 13

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

9/10 Wonderful! (296 reviews)

The Commonwealth

Downtown Richmond

Save 100% on your flight

$761

per person

Nov 8 - Nov 13

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

8.8/10 Excellent! (1,406 reviews)

Kingsmill Resort

Kingsmill

$727

per person

Nov 8 - Nov 13

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

8.6/10 Excellent! (1,004 reviews)

The Berkeley Richmond, Outset Collection by Hilton

Downtown Richmond

$759

per person

Nov 8 - Nov 13

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

8.8/10 Excellent! (1,350 reviews)

Lovely property with very friendly staff. Great location

Reviewed on Sep 30, 2026

Hilton Richmond Downtown

Downtown Richmond

$648

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

8.2/10 Very Good! (1,007 reviews)

I love this hotel!!!! Clean, smell good, restaurant good!

Reviewed on Sep 27, 2026

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5* Ski vacations in Southside

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

The Jefferson Hotel

Downtown Richmond

$1,156

per person

Dec 23 - Dec 27

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Richmond (RIC)

9.8/10 Exceptional! (1,008 reviews)

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3 Night Ski vacations in Southside

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

The Commonwealth

Downtown Richmond

$576

per person

Dec 13 - Dec 16

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Richmond (RIC)

8.8/10 Excellent! (1,406 reviews)

Kingsmill Resort

Kingsmill

$631

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

New York (NYC) to Richmond (RIC)

8.6/10 Excellent! (1,004 reviews)

The Berkeley Richmond, Outset Collection by Hilton

Downtown Richmond

$720

per person

Nov 27 - Nov 30

found 3 hours ago

Roundtrip flight included

Houston (IAH) to Richmond (RIC)

8.8/10 Excellent! (1,350 reviews)

Lovely property with very friendly staff. Great location

Reviewed on Sep 30, 2026

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4 Night Ski vacations in Southside

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

Westgate Historic Williamsburg Resort

Midtown

$565

per person

Dec 7 - Dec 11

found 5 hours ago

Roundtrip flight included

New York (NYC) to Richmond (RIC)

8.6/10 Excellent! (1,000 reviews)

The first room I was booked into had a truly terrible smell — bad enough to ask for a room change. The staff was very cooperative, but they moved me into a pretty musty smelling room with a broken AC/HVAC and a very loud portable AC/filtration unit. I’ve stayed there multiple times in the past and always had great experiences. But after this, not sure I can bring myself to go back.

Reviewed on Sep 20, 2026

Kingsmill Resort

Kingsmill

$598

per person

Dec 6 - Dec 10

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Richmond (RIC)

8.6/10 Excellent! (1,004 reviews)

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$695

per person

Dec 7 - Dec 11

found 5 hours ago

Roundtrip flight included

New York (NYC) to Richmond (RIC)

8.8/10 Excellent! (885 reviews)

Very pleasurable stay at the Griffen. Arrived around 12 noon and was able to check in immediately. Room was clean and facilities were in good working order. Needed a ground level room due to age which was provided.

Reviewed on Sep 30, 2026

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What are some things I should consider when booking a Southside 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 Southside ski packages?

Right now, ski trips start at just $565. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Southside?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Southside. 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 Southside cost?

Sensational ski trips to Southside start from $565. 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 Southside?

The best time to hit the slopes in Southside 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 Southside 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 Southside 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 Southside with Expedia?

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