Ski Vacations in Martha's Vineyard 2026

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Flight and Ski hotel deals in Martha's Vineyard

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

Margaritaville Resort Cape Cod

CA $1,254

per person

Oct 15 - Oct 20

found 8 hours ago

Roundtrip flight included

Toronto (YYZ) to Hyannis (HYA)

8.6/10 Excellent! (664 reviews)

Wequassett Resort and Golf Club

CA $2,326

per person

Oct 15 - Oct 20

found 8 hours ago

Roundtrip flight included

Toronto (YYZ) to Hyannis (HYA)

9.4/10 Exceptional! (265 reviews)

Our stay at Wequassett Resort and Golf Club was nothing short of extraordinary. From the moment we arrived, we were surrounded by beauty, elegance, and exceptional hospitality. Our Premier Waterview Cottage was absolutely breathtaking. The accommodations were beautiful, luxurious, and exceeded our expectations in every way. Waking up to the stunning waterfront views made our stay even more special. The dining was equally impressive. Every meal was delicious, beautifully prepared, and a true reflection of the quality and care that went into every aspect of our experience. What truly set Wequassett apart, however, was the incredible staff. Each person we encountered went above and beyond to make our 30th anniversary celebration feel truly special. Their genuine warmth, thoughtfulness, and attention to every detail made us feel incredibly welcomed and cared for. Celebrating 30 years of marriage at such a beautiful and extraordinary resort was a memory we will treasure forever. Wequassett gave us far more than a wonderful vacation—it gave us an unforgettable celebration filled with beautiful moments, exceptional service, and memories we will cherish for years to come. We cannot thank the entire Wequassett team enough and are already looking forward to returning. Absolutely beautiful, breathtaking, and truly unforgettable!

Reviewed on Aug 8, 2026

Faraway Martha's Vineyard

CA $2,136

per person

Sep 24 - Sep 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Vineyard Haven (MVY)

9/10 Wonderful! (1,000 reviews)

We LOVED our stay at Faraway - the pool was amazing, staff was super helpful. They had a very convenient messaging system for requests. The staff recommended the Pelican Club for dinner, which is basically right on-site, but we tried to get in multiple times and there was always a wait! The food at their snack bar was really good for lunch. The location was incredible - it was our first time in Martha's Vineyard and we feel we got so spoiled!!

Reviewed on Aug 11, 2026

Harbor View Hotel

CA $3,026

per person

Sep 24 - Sep 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

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5* Ski holidays in Martha's Vineyard

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

Wequassett Resort and Golf Club

CA $2,326

per person

Oct 15 - Oct 20

found 8 hours ago

Roundtrip flight included

Toronto (YYZ) to Hyannis (HYA)

9.4/10 Exceptional! (265 reviews)

Reviewed on Aug 8, 2026

Harbor View Hotel

CA $3,026

per person

Sep 24 - Sep 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Martha's Vineyard

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3 Night Ski holidays in Martha's Vineyard

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

Faraway Martha's Vineyard

CA $2,136

per person

Sep 24 - Sep 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Vineyard Haven (MVY)

9/10 Wonderful! (1,000 reviews)

Reviewed on Aug 11, 2026

Harbor View Hotel

CA $3,026

per person

Sep 24 - Sep 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

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See all available trips from Columbus to Martha's Vineyard

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4 Night Ski holidays in Martha's Vineyard

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

Anchor In Distinctive Waterfront Lodging

CA $1,421

per person

Oct 8 - Oct 12

found 8 hours ago

Roundtrip flight included

Toronto (YYZ) to Hyannis (HYA)

9.4/10 Exceptional! (1,006 reviews)

Inn on Main

CA $1,602

per person

Oct 8 - Oct 12

found 8 hours ago

Roundtrip flight included

Toronto (YYZ) to Hyannis (HYA)

10/10 Exceptional! (78 reviews)

Very accommodating hosts , Dave & Ruta. Delicious 2 course breakfast.Room was clean, very comfortable and great amenities. Hosts were very helpful regarding dining and touring ideas. Highly recommend

Reviewed on Aug 8, 2026

The Villa Callo Inn

CA $1,559

per person

Oct 8 - Oct 12

found 8 hours ago

Roundtrip flight included

Toronto (YYZ) to Hyannis (HYA)

9/10 Wonderful! (2 reviews)

Really enjoyed our stay. Staff went above and beyond, breakfast was top notch and the Location was great.

Reviewed on Aug 11, 2026

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What are some benefits when booking ski vacations in Martha's Vineyard?

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 Martha's Vineyard?

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 Martha's Vineyard, 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 Martha's Vineyard with some as cheap as CA $1,254. 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 Martha's Vineyard. 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 21 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 Martha's Vineyard.

Can I book all-inclusive ski vacations in Martha's Vineyard?

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 Martha's Vineyard 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 Martha's Vineyard'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 Martha's Vineyard?

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 Martha's Vineyard. 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 21. With Expedia Rewards, you can earn points towards your next booking.