Pilgrims Rest Winter Rentals & Holiday Homes

Discover winter rentals Pilgrims Rest - We found 50 exact matches

About Pilgrims Rest Winter Rental on SunSkiResorts

Planning a winter vacation in Pilgrims Rest? Discover 50 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Pilgrims Rest 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 Pilgrims Rest start at US $84. The most popular properties in Pilgrims Rest 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 Pilgrims Rest, 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 Pilgrims Rest and unlock incredible deals.

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Frequently Asked Questions About Pilgrims Rest Winter Rentals

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

The average cost for winter rentals in Pilgrims Rest is $84 per night. SunSki has a wide list of great winter places to stay near Pilgrims Rest 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 Pilgrims Rest that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Pilgrims Rest on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Pilgrims Rest to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 50 private swimming pools or indoor pools accommodations near Pilgrims Rest along with other great amenities.

About 50 holiday rentals in Pilgrims Rest 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 Pilgrims Rest for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Pilgrims Rest with all the best amenities for your next trip.