Keystone Ski Vacations 2026

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Top Ski vacation packages in Keystone

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

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$735

per person

Nov 6 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,173 reviews)

Loved the place, I was so impressed how clean it was. Beach view is perfect.

Reviewed on Sep 4, 2026

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$838

per person

Nov 5 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,160 reviews)

Good stay.

Reviewed on Sep 4, 2026

CW Resort

Save 100% on your flight

$770

per person

Oct 14 - Oct 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (117 reviews)

Wyndham Grand Clearwater Beach

Save 100% on your flight

$1,284

per person

Oct 7 - Oct 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (3,767 reviews)

Amazing , perfect resort !

Reviewed on Sep 4, 2026

The Hotel Zamora

Save 100% on your flight

$755

per person

Nov 6 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.8/10 Excellent! (397 reviews)

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See all available trips from Columbus to Keystone

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5* Ski vacations in Keystone

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

The Adaline

Hyde Park

$1,001

per person

Nov 10 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (74 reviews)

The Gemma by Brightwild

Save 100% on your flight

$2,562

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.8/10 Exceptional! (6 reviews)

The Jade House is in an excellent location only a block from the beach and short walk to restaurants, shops, and bars. Communication with the management company was difficult through Expedia. Even when I called directly, one of the three client service agents was not helpful whatsoever. However, once I was given the number to text, communication was much better. The pool/ hot tub area is perfect. The house is very comfortable. Only decks are narrow (only stand); ocean view is from one of theses.

Reviewed on Jul 30, 2026

Indian Rocks Escape

Save 100% on your flight

$1,931

per person

Nov 10 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

No reviews

Don't see what you're looking for?

See all available trips from Columbus to Keystone

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3 Night Ski vacations in Keystone

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

CW Resort

$691

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (117 reviews)

Wyndham Grand Clearwater Beach

$797

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (3,767 reviews)

Amazing , perfect resort !

Reviewed on Sep 4, 2026

Ocean Club Treasure Island Hotel

Sunshine Beach

$693

per person

Nov 5 - Nov 8

found 15 hours ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,173 reviews)

Loved the place, I was so impressed how clean it was. Beach view is perfect.

Reviewed on Sep 4, 2026

Don't see what you're looking for?

See all available trips from Columbus to Keystone

View all trips

4 Night Ski vacations in Keystone

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

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$570

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,173 reviews)

Loved the place, I was so impressed how clean it was. Beach view is perfect.

Reviewed on Sep 4, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,056

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (584 reviews)

The room was immaculate and the beds and pillows were the comfiest I have ever slept in. The room had everything we needed to make our stay comfortable. The location is perfect and the beach there is amazing. We have stayed here 4 times now and will be back again. This is a small, locally owned resort and they take great pride in the property. We absolutely love it.

Reviewed on Sep 3, 2026

Wyndham Grand Clearwater Beach

Save 100% on your flight

$880

per person

Oct 14 - Oct 18

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (3,767 reviews)

Amazing , perfect resort !

Reviewed on Sep 4, 2026

Don't see what you're looking for?

See all available trips from Columbus to Keystone

View all trips

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

Right now, ski trips start at just $570. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Keystone?

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

Sensational ski trips to Keystone start from $570. 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 Keystone?

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

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