Pinehurst Winter Rentals & Holiday Homes

Discover winter rentals Pinehurst - We found 254 exact matches

About Pinehurst Winter Rental on SunSkiResorts

Planning a winter vacation in Pinehurst? Discover 254 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Pinehurst, FL 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 Pinehurst start at US $301. The most popular properties in Pinehurst 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 Pinehurst, 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 Pinehurst and unlock incredible deals.

Show more
Show less

Winter Rental: Explore Top Destinations

Frequently Asked Questions About Pinehurst Winter Rentals

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

The average cost for winter rentals in Pinehurst is $301 per night. SunSki has a wide list of great winter places to stay near Pinehurst 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 Pinehurst that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Pinehurst on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Pinehurst to find what works for you.
As of 2026, the data from SunSkiResorts shows that there are over 254 private swimming pools or indoor pools accommodations near Pinehurst along with other great amenities.

About 254 holiday rentals in Pinehurst 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 Pinehurst for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Pinehurst with all the best amenities for your next trip.