Winston - Salem Ski Vacations 2026

Photo by Visit Winston Salem

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Top Ski vacation packages in Winston - Salem

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

Exec Suite King Bed Hot Tub Gym Laundry

$688

per person

Apr 16 - Apr 21

found 18 hours ago

Roundtrip flight included

New York (NYC) to Greensboro (GSO)

No reviews

Heated Pool King Bed Jacuzzi Bath Arcade

Save 100% on your flight

$1,301

per person

Apr 16 - Apr 21

found 18 hours ago

Roundtrip flight included

New York (NYC) to Greensboro (GSO)

8/10 Very Good! (1 review)

The house was very clean, comfortable, and nicely maintained, which we really appreciated during our stay. However, there were two downsides to be aware of. First, after booking, the owner asked us to pay an extra money for cleaning fee, even though it was not clearly listed in the Expedia booking details. I chose not to argue since I didn’t want to ruin our family trip, but future guests should expect additional charges. Second, privacy was an issue the owner lives in the basement, and it felt uncomfortable at times, especially with my child playing and moving around. Overall, it’s a nice property, but keep in mind the extra costs and limited privacy.

Reviewed on Sep 30, 2025

King Beds Hot Tub Arcade Grill & Firepit

Save 100% on your flight

$1,112

per person

Apr 16 - Apr 21

found 18 hours ago

Roundtrip flight included

New York (NYC) to Greensboro (GSO)

8/10 Very Good! (1 review)

KingBed PetFriendly Washer Dryer Sleep16

Save 100% on your flight

$2,780

per person

Apr 16 - Apr 21

found 18 hours ago

Roundtrip flight included

New York (NYC) to Greensboro (GSO)

No reviews

O.Henry Hotel

Save 100% on your flight

$934

per person

Apr 16 - Apr 21

found 15 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Greensboro (GSO)

9.8/10 Exceptional! (724 reviews)

Green Valley Grill is fantastic, the hotel has charm, love it!

Reviewed on Jan 18, 2026

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3 Night Ski vacations in Winston - Salem

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

DoubleTree by Hilton Winston Salem - University

$352

per person

Mar 19 - Mar 22

found 8 hours ago

Roundtrip flight included

New York (NYC) to Greensboro (GSO)

8.4/10 Very Good! (1,000 reviews)

Spotless, spacious, and super comfortable (Junior Suite).

Reviewed on Dec 1, 2025

O.Henry Hotel

$603

per person

Mar 19 - Mar 22

found 8 hours ago

Roundtrip flight included

New York (NYC) to Greensboro (GSO)

9.8/10 Exceptional! (724 reviews)

Green Valley Grill is fantastic, the hotel has charm, love it!

Reviewed on Jan 18, 2026

Proximity Hotel

$593

per person

Mar 19 - Mar 22

found 8 hours ago

Roundtrip flight included

New York (NYC) to Greensboro (GSO)

9.6/10 Exceptional! (879 reviews)

Great hotel, exceptional service, great restaurant. Will stay here agin when in the area without hesitation

Reviewed on Jan 23, 2026

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4 Night Ski vacations in Winston - Salem

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

Country Inn & Suites by Radisson, Burlington (Elon), NC

$579

per person

Apr 20 - Apr 24

found 1 hour ago

Roundtrip non-stop flight included

Boston (BOS) to Greensboro (GSO)

9.2/10 Wonderful! (1,000 reviews)

Great staff. Always a pleasant home away from home

Reviewed on Jan 16, 2026

La Quinta Inn & Suites by Wyndham Greensboro NC

$633

per person

Apr 20 - Apr 24

found 1 hour ago

Roundtrip non-stop flight included

Boston (BOS) to Greensboro (GSO)

8/10 Very Good! (1,002 reviews)

Room and hotel was very clean. Front desk staff was extremely friendly

Reviewed on Dec 27, 2025

Tru By Hilton Burlington

$597

per person

Apr 20 - Apr 24

found 1 hour ago

Roundtrip non-stop flight included

Boston (BOS) to Greensboro (GSO)

9.2/10 Wonderful! (760 reviews)

Rooms are warm and comfortable. No microwave in room but there is one in lobby. Great continental breakfast. Hot and variety. Great for travelers.

Reviewed on Jan 26, 2026

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See all available trips from Columbus to Winston - Salem

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What are some things I should consider when booking a Winston - Salem 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 Winston - Salem ski packages?

Right now, ski trips start at just $352. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Winston - Salem?

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

Sensational ski trips to Winston - Salem start from $352. 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 Winston - Salem?

The best time to hit the slopes in Winston - Salem 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 Winston - Salem 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 Winston - Salem 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 Winston - Salem with Expedia?

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