Woodside Winter Rentals & Holiday Homes

Discover winter rentals Woodside - We found 34 exact matches

About Woodside Winter Rental on SunSkiResorts

Planning a winter vacation in Woodside? Discover 34 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Woodside, CA perfect for your seasonal escape. Our listings include private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments. SunSki's winter vacation homes feature top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Winter accommodations in Woodside start at US $997. The most popular properties in Woodside include cabins, bungalows, and rental homes. Planning a snowboarding adventure? Explore our snowboard-friendly ski resorts, chalets, and cabins available for short-term or long-term stays. Whether it's a weekend getaway, monthly retreat, or an extended stay, SunSki ensures a memorable winter trip.

To book your winter vacation homes in Woodside, visit SunSki's filter option, enter your travel dates, narrow down your preferences, and choose from our extensive list of rentals hassle-free. Explore our interactive map to uncover all accommodations in or around Woodside and unlock incredible deals.

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Frequently Asked Questions About Woodside Winter Rentals

There are a lot of options in Woodside. If you plan on staying in the Woodside area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Woodside:

The average cost for winter rentals in Woodside is $997 per night. SunSki has a wide list of great winter places to stay near Woodside that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Woodside that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Woodside on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Woodside to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 34 private swimming pools or indoor pools accommodations near Woodside along with other great amenities.

About 34 holiday rentals in Woodside boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Woodside for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Woodside with all the best amenities for your next trip.