Ski-in/Ski-out vacation rentals in Massachusetts

This home was the perfect place for our family/friends gathering. Location was fantastic - just a short 1-2 min walk to the ski-in spot, making it incredibly convenient for hitting the slopes with little ones. The host was exceptionally informative and friendly, ensuring we had everything for a comfy stay. Kids had fun sledding between the houses and grownups loved the hot tub.

Lovely one night stay! Perfect location on the mountain, super clean and Zaighum was very helpful and accommodating with an early check in. Would highly recommend!

Highly recommend this cute lake house! Very peaceful and scenic. House was clean and Tyler was a great host, very responsive.

Quaint, comfortable countryside home. Whenever we had questions, Harriet and Marie responded promptly. Beautiful surroundings.

We stayed at Kim’s cozy cabin at Jiminy Peak for two nights. There was plenty of space for everyone and the place was immaculate. The place is so clean from the floor to every corner and ceiling, it makes you feel so comfortable and safe, knowing she took care of every detail. The place has a ton of electrical outlets which is a very nice plus this day and age with kids. The location is great as well. A short walk to John Harvards so the mountain is easily accessible. Big tip, since you’re staying at the cabin, rent your equipment and get your passes the night before, it saves so much time. You can be on the mountain without having to walk to the main lodge. We had an amazing time at her cabin and I would highly recommend it. It’s a perfect stay for a weekend ski or longer.

We had an awesome time at Kathryn and Rob's condo. Kathryn was extremely responsive to my many questions, and flexible with timing. She asked ahead of time if we'd like to arrive early because of the impending snow storm which was very considerate. The house was clean and had everything we could possibly need. The kids (10,8, an 5) loved the basement foosball table and numerous board games, and the grownups enjoyed the many puzzles! The bed situation was perfect for spreading out so each person could have their own space. Kitchen was well-stocked and there really wasn't anything we needed that wasn't available. It looks even better in person than in the pictures. In addition, the location was super convenient for getting to the slope nice and early. Can't wait to come back!

Thank you Carl for an excellent stay! We traveled with 3 adults and 6 kids and everyone had a wonderful stay. We watched a movie, enjoyed the downstairs space, ordered take out from bluebird (delicious!), and walked down the road to ski straight down a green to the lodge. What stood out most though was Carl’s responsiveness and kindness. Looking forward to our next trip!

Picturesque location! Beautiful and peaceful ! Thanks for a lovely getaway! The WiFi was great and perfect for a day of remote working.

This was a great place to stay as a family for a ski trip! Easy ski on/ski off access to the mountain with ski lockers was a huge plus. Easy enough to walk to a few restaurants. The kids love the movie theater, pool and game room. Very clean and friendly/helpful staff at front desk.

This place is a dream and Carol was such a kind and thoughtful host. We came here to celebrate my partner's birthday and it was everything we hoped it would be and more. The view the first morning of the surrounding hills in peak foliage was amazing to wake up to. And the big tub was so luxurious for taking baths. And it's a very close drive to Northampton and the surrounding areas. Our only regret was that we couldn't have stayed here longer. Will definitely save to come back and visit!

We had such a great time at Rob&Julia's place. Very good communication, great location, the place was sparkling clean! I will definitely come back again with my family! One of my best experiences

My two adult children and I stayed here with our two dogs while my wife was having surgery in Boston. The location was great. Car ride to the Longwood medical area was about 25 minutes. The neighborhood consists of single family homes on small lots, not at all fancy but entirely safe as far as we could tell. We were just a few short blocks from a school playing field where leashed dogs were welcome, and other dog-walkers were often on the street in the morning and evening. The house is a bit quirky. There is no seating in the kitchen, but the dining area is very spacious although located down a short hallway from the kitchen. Each of the three bedrooms was more than ample and very quiet at night. We slept well. As we stayed more than a week we were grateful that laundry facilities were present in the basement. Roosevelt was an excellent host and quick to respond to my requests. I would definitely stay in his place again should a similar situation arise.

We gather with a large group of friends every year and this was an ideal location for our reunion. There is plenty of space to spread out, a well-equipped kitchen, and a spacious dining area. There are wonderful trails to hike (or ski later in the season)

Our family loved the stay ! Place was beautiful, clean and with lots of activities for the kids. Highly recommend and definitely coming back soon.

We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!

Very nice spot for one person or a couple. Convenient access to JP base area and amenities. Neat and tidy space, nicely appointed. Great communication from owner.

Perfect home base for skiing at Jiminy! It was great for me and my kid plus we got to enjoy the hot tub, pool, breakfast at the country store and dinner at bluebird & co. Justine was a great and communicative host - we hope to return soon!

We had a fabulous time up at Jiminy Peak and being right on the mountain at Shana’s place made it very easy to enjoy the many things to do. Shana is a great host and her unit was perfect for our family of 5. Our younger two tried counting all of the gnomes in every room. We definitely recommend staying at Shana’s place, she is very easy to work with and quick to answer any questions. Thanks again A+

Great stay at Renee’s! Right off the lifts. Easy storage for skis and ski on ski off. Clean room with all the necessary amenities. Restaurant in the building if you don’t want to venture far. Cozy fireplace in the lobby with coffee and hot chocolate bar. Overall a great long weekend at Jiminy. Thnx!

Our second year staying here and making wonderful family memories. The condo was clean and cozy. Gorgeous view of the mountain and easy ski in/ski out. Everything you need is stocked and ready. We look forward to rebooking for next year.

Had an amazing stay! The location couldn't be better for skiing at Berkshire East—it’s literally just across the parking lot, which made it so easy to get on and off the slopes. The house itself was super warm and cozy, perfect for relaxing after a day on the mountain. The kitchen was well-equipped, so we were able to cook up some great meals without any issues. Definitely planning to stay here again next time we're skiing at Berkshire East! Highly recommend!