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.

Our family had a great stay at Smiling Dog Meadow and looking forward to returning!

This place is worth every penny. Beautiful location on the mountain. Could not have asked for a better home to stay in.

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!

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

This is the second year we have stayed at Morgan’s home, and it is spacious, welcoming, clean, and very well equipped! This year we had much better conditions than last year (snow!) and walked down the road and skied right on to the mountain. It’s a few minutes, but is not any worse than trying to find a parking space when there are none and walking up all of those steps! It was awesome! Morgan is attentive and communicative and our large family absolutely love staying and can’t wait to come back!

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!

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

Great location, great owner, and wonderful stay. We loved walking all around the neighborhood. The screened in porch was lovely. Wonderful backyard. Very nice sheets and towels. Excellent wi-fi and TV. We couldn't have been happier here.

I had the best night of sleep I have had in a long time at The Maple House. The property is peaceful and beautiful. Cool mountain air blows in through your room and you can hear the critters in the distance. Rebecca prepares a lovely breakfast for you in the morning. If you are looking for a breath of fresh air in the country, this bed and breakfast is for you!

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.

A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.

Hamilton is a wonderful host and the area is always beautiful and fun.

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+

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.

We had a great stay here. It was very close to the ski lifts, and the ski locker was directly across the hall. It made for a very enjoyable and easy skiing experience. Jiminy Peak is a great place to ski at with a variety of trails for all skill levels, and even though it was a school vacation week/weekend, the lift lines were never long. Margaret was very responsive to any questions we had and made the process easy. We loved it!

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!!!

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!