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Oakland Winter Rentals & Holiday Homes

Discover winter rentals Oakland - We found 266 exact matches

About Oakland Winter Rental on SunSkiResorts

Planning a winter vacation in Oakland? Discover 266 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Oakland, IL 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 Oakland start at US $423. The most popular properties in Oakland 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 Oakland, 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 Oakland and unlock incredible deals.

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Frequently Asked Questions About Oakland Winter Rentals

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

The average cost for winter rentals in Oakland is $423 per night. SunSki has a wide list of great winter places to stay near Oakland 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 Oakland that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Oakland on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Oakland to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 266 private swimming pools or indoor pools accommodations near Oakland along with other great amenities.

About 266 holiday rentals in Oakland 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 Oakland for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Oakland with all the best amenities for your next trip.