1. USA
  2. Massachusetts
  3. Boston
  4. Ski Chalets

Boston Ski Chalets Rentals & Holiday Homes

Find the best ski chalets in Boston - We found 7513 exact matches

About Boston Ski Chalets on PickleTrip

Ski resorts and ski-chalets are a popular choice in Boston. At PickleTrip™, we offer more than 7513 ski chalets near Boston to suit your budget and preferences. These chalets are a great option for those looking for a place to stay while enjoying their pickleball game, skiing and snowboarding adventures in the winter or hiking in the summer. PickleTrip™ vacation homes are perfect for families, groups, friends, or wedding retreats, and they come with great amenities.

PickleTrip™ offers several luxury chalets for those who love outdoor travel experiences while still having access to top-notch pickleball courts and nearby facilities. The site provides dog-friendly and self-catering ski chalet rentals near Boston, so you can take on all your adventures with ease, then come back to your rental for more comfort and pleasure.

If you love chalet skiing with patio options or private chalets, there are more than 7513 of them available near Boston. Some examples of these chalets include romantic chalets, mountain chalets, catered ski chalets, and self-catering ski chalets. Your vacation gets better as you book your holiday chalet with PickleTrip™ for your next trip.

Show more
Show less

Ski Chalets: Explore Top Destinations

Explore More

Frequently Asked Questions About Boston Rental Ski Chalets

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

There are many ski chalets available in Boston; however, here are the most popular ski chalets listed in Boston:
PickleTrip offers availability throughout the year, but you can book pre-Christmas, mid-January, or before and after the school break at Easter are the best times for renting in Boston.
At PickleTrip most of our ski chalets are perfect for families. Check out the complete list of ski chalets in Boston to find what works for you.
Yes, there are 7513 self-catering family ski chalet in Boston that have hot tubs & other amenities.
There are more than 7513 luxury ski chalets for families or group in or near Boston, with other amenities available according to data 2026 from PickleTrip.
Yes, there are more than 7513 pet friendly ski chalets that are available in Boston.
We have a list of top-rated ski chalets for families to stay at Christmas or New Year's holiday near Boston.