Jamaica Plain Winter Rentals & Holiday Homes

Discover winter rentals Jamaica Plain - We found 17 exact matches

About Jamaica Plain Winter Rental on SunSkiResorts

Planning a winter vacation in Jamaica Plain? Discover 17 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Jamaica Plain, 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 Jamaica Plain start at US $391. The most popular properties in Jamaica Plain 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 Jamaica Plain, 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 Jamaica Plain and unlock incredible deals.

Show more
Show less

Frequently Asked Questions About Jamaica Plain Winter Rentals

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

The average cost for winter rentals in Jamaica Plain is $391 per night. SunSki has a wide list of great winter places to stay near Jamaica Plain 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 Jamaica Plain that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Jamaica Plain on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Jamaica Plain to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 17 private swimming pools or indoor pools accommodations near Jamaica Plain along with other great amenities.

About 17 holiday rentals in Jamaica Plain 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 Jamaica Plain for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Jamaica Plain with all the best amenities for your next trip.