Winter Park Ski Chalets Rentals & Holiday Homes

Find the best ski chalets in Winter Park - We found 9 exact matches

From US $1,584 per night
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New
4 Bedrooms 10 Guests
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New
4 Bedrooms 8 Guests
From US $1,217 per night
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New
4 Bedrooms 10 Guests
From US $1,074 per night
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New
4 Bedrooms 8 Guests
From US $1,470 per night
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New
4 Bedrooms 12 Guests
From US $1,296 per night
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New
4 Bedrooms 8 Guests
From US $1,197 per night
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New
4 Bedrooms 12 Guests
From US $508 per night
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New
4 Bedrooms 12 Guests
From US $487 per night
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New
4 Bedrooms 12 Guests

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2 Bedrooms 8 Guests
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4 Bedrooms 14 Guests
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1 Bedroom 2 Guests
From US $1,008 per night
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10.0 (2 Reviews)
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2 Bedrooms 8 Guests
From US $293 per night
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3 Bedrooms 9 Guests
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2 Bedrooms 8 Guests

About Winter Park Ski Chalets on Vacation Cottage

Seeking a cozy retreat to relax before and after hitting the slopes? Look no further. Ski resort villas and chalets are a popular choice in Winter Park. At Vacation Cottage, we offer over 9 luxury ski chalets near Winter Park tailored to your preferences. These mountain retreats provide comfort and enhance your skiing and snowboarding experiences. Vacation Cottage vacation homes cater to families, groups, friends, or wedding retreats, offering outstanding amenities.

If you fancy ski chalets with patio options or private lodges, there are more than 9 available near Winter Park. From romantic chalets to mountain retreats, catered villas, and self-catering ski chalets, you'll find a variety of upscale stays to choose from. Your next vacation becomes a reality with Vacation Cottage.

Prepare for your next ski getaway by booking a top-rated ski resort or villa in Winter Park offering picturesque views of the surrounding scenery. Whether you seek a romantic weekend retreat, a spacious chalet for family or friends, or a solo adventure, premium options await with Vacation Cottage. Life is Better at the Cottage with Vacation Cottage.

Frequently Asked Questions About Winter Park Rental Ski Chalets

Which is the best ski chalet in Winter Park?

There are many ski chalets available in Winter Park; however, here are the most popular ski chalets listed in Winter Park:

What is the best time to book a ski chalet near Winter Park?

Vacation Cottage offers availability throughout the year, but you can book pre-Christmas, mid-January, or before and after the school break at Easter are the best times for renting in Winter Park.

What are the most family-friendly ski chalets Winter Park?

At Vacation Cottage most of our ski chalets are perfect for families. Check out the complete list of ski chalets in Winter Park to find what works for you.

Can we get a self-catering family ski chalet in Winter Park?

Yes, there are 9 self-catering family ski chalet in Winter Park that have hot tubs & other amenities.

What are the best luxury ski chalets for families near Winter Park?

There are more than 9 luxury ski chalets for families or group in or near Winter Park, with other amenities available according to data 2025 from Vacation Cottage.

Can we bring our dog to our ski chalet in Winter Park?

Yes, there are more than 9 pet friendly ski chalets that are available in Winter Park.

Which ski chalets are best for families at Christmas or New Year?

We have a list of top-rated ski chalets for families to stay at Christmas or New Year's holiday near Winter Park.