Ten Thousand Islands Ski Vacations 2026

Top Ski vacation packages in Ten Thousand Islands

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

Innovation Hotel

Save 100% on your flight

$580

per person

Nov 29 - Dec 3

found 1 day ago

Roundtrip flight included

Cleveland (CLE) to Fort Myers (RSW)

9.8/10 Exceptional! (649 reviews)

We were there for a girl's weekend. The hotel is beautiful and customer service amazing. We had breakfast both mornings and ate at the bar one afternoon. Our experience was nothing short of perfect. I look forward to returning!

Reviewed on Sep 15, 2026

The Perry Hotel Naples

Save 100% on your flight

$1,043

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Save 100% on your flight

$633

per person

Dec 6 - Dec 11

found 8 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.4/10 Exceptional! (108 reviews)

Beautiful resort.. all of the food from by the pool, to the dining hall, to the higher end are all incredible- the only down side is the food is pricey.

Reviewed on Sep 17, 2026

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight

$909

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (1,012 reviews)

Loved the lazy river, staff was pleasant and helpful, and we loved our 1-bedroom villa.

Reviewed on Sep 15, 2026

Shell Island Beach Club

East End

Save 100% on your flight

$1,267

per person

Nov 28 - Dec 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (25 reviews)

This well-equipped apartment overlooks the grounds and swimming pool with views of the beach just yards away. Fully restored after the devastation from hurricane Ian 4 years ago it’s in great shape and we had a wonderful stay. The staff work tirelessly to keep the place as it should be and nothing was too much trouble. I can’t recommend it highly enough.

Reviewed on Sep 6, 2026

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5* Ski vacations in Ten Thousand Islands

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

Sundial Beach Resort & Spa

Mid Island

Save 100% on your flight

$1,273

per person

Dec 3 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (2,690 reviews)

Sundial Resort is the best place to stay on Sanibel! We have been there numerous times, and also stayed in other resorts and condos on Sanibel and Captive, but Sundial has the best vibe, family entertainment and great food!

Reviewed on Sep 15, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

Save 100% on your flight

$2,719

per person

Dec 1 - Dec 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (34 reviews)

The Ritz-Carlton Naples, Tiburón

$2,125

per person

Nov 10 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (681 reviews)

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3 Night Ski vacations in Ten Thousand Islands

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

Inn at Pelican Bay

Pelican Bay

$610

per person

Oct 31 - Nov 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,004 reviews)

The pool area was on the small side, which I liked. The hotel was quiet during the week. Breakfast had good options. Pancake machine, waffle machine, various doughnuts, yogurt with toppings, cereal, hard boiled eggs and a variety of bread products. Good outdoor seating with umbrellas. What I didn't like was Expedia had to remind me to ask for the perks I was supposed to get at check in. When I asked the front desk, they saw it on the screen but would only offer it to me if I stated what it was exactly. I was disappointed by that.

Reviewed on Sep 17, 2026

The Perry Hotel Naples

$980

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Hyatt Vacation Club at Coconut Cove, Bonita Springs

$700

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (1,012 reviews)

Loved the lazy river, staff was pleasant and helpful, and we loved our 1-bedroom villa.

Reviewed on Sep 15, 2026

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4 Night Ski vacations in Ten Thousand Islands

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Olde Marco Island Inn and Suites

Olde Marco

$590

per person

Nov 27 - Dec 1

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

8.8/10 Excellent! (1,001 reviews)

Loved our stay and the screened in balcony was terrific

Reviewed on Sep 14, 2026

The Perry Hotel Naples

Save 100% on your flight

$822

per person

Nov 12 - Nov 16

found 9 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

Tween Waters Island Resort & Spa

Save 100% on your flight

$647

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Fort Myers (RSW)

8.6/10 Excellent! (1,005 reviews)

Reviewed on Sep 17, 2026

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What are some things I should consider when booking a Ten Thousand Islands 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 Ten Thousand Islands ski packages?

Right now, ski trips start at just $580. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Ten Thousand Islands?

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

Sensational ski trips to Ten Thousand Islands start from $580. 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 Ten Thousand Islands?

The best time to hit the slopes in Ten Thousand Islands 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 Ten Thousand Islands 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 Ten Thousand Islands 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 Ten Thousand Islands with Expedia?

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