Great Barrington Winter Rentals & Holiday Homes

Discover winter rentals Great Barrington - We found 224 exact matches

About Great Barrington Winter Rental on SunSkiResorts

Planning a winter vacation in Great Barrington? Discover 224 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Great Barrington, MA 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 Great Barrington start at US $631. The most popular properties in Great Barrington 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 Great Barrington, 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 Great Barrington and unlock incredible deals.

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Frequently Asked Questions About Great Barrington Winter Rentals

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

The average cost for winter rentals in Great Barrington is $631 per night. SunSki has a wide list of great winter places to stay near Great Barrington 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 Great Barrington that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Great Barrington on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Great Barrington to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 224 private swimming pools or indoor pools accommodations near Great Barrington along with other great amenities.

About 224 holiday rentals in Great Barrington 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 Great Barrington for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Great Barrington with all the best amenities for your next trip.