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Ski-in/Ski-out vacation rentals in Massachusetts
Find and book unique ski-in/ski-out homes on Airbnb
Top-rated ski-in/ski-out rentals in Massachusetts
Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Massachusetts ski-in/ski-out rentals
Ski-in/ski-out house rentals
![](https://a0.muscache.com/im/pictures/miso/Hosting-1034056190247350198/original/bd850cb8-65f6-4340-acd8-55abcda8dcdc.jpeg?im_w=720)
Home in Hancock
5 out of 5 average rating, 14 reviewsSunshine & Summertime Left Bank Lodge
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6NjA4NDMzNTIyNzI4NDI2MjA1/original/91d0c738-0666-480e-9be8-fc8b0639ffbe.jpeg?im_w=720)
Home in Hancock
5 out of 5 average rating, 25 reviewsCozy Cabin in Berkshires Resort Property
![](https://a0.muscache.com/im/pictures/miso/Hosting-750837149782132613/original/e601bf5c-9cac-40ad-875c-e878c8022385.jpeg?im_w=720)
Home in Hancock
4.94 out of 5 average rating, 18 reviewsCondo on the mountain
![](https://a0.muscache.com/im/pictures/6c69e82f-1018-4176-b248-970b3c9b779e.jpg?im_w=720)
Home in Worthington
4.67 out of 5 average rating, 9 reviewsA simple kind of paradise
![](https://a0.muscache.com/im/pictures/dbf12763-8ffd-456c-99d6-eea34f114bd9.jpg?im_w=720)
Home in Hancock
4.78 out of 5 average rating, 9 reviewsBeautiful 4 Bedroom Townhouse in the Berkshires
![](https://a0.muscache.com/im/pictures/miso/Hosting-50126571/original/ca243c53-eb9b-4ad3-b8db-7e0722ebe02d.jpeg?im_w=720)
Home in Hancock
4.85 out of 5 average rating, 20 reviewsMountainside: Large 3-level Jiminy Peak Home
![](https://a0.muscache.com/im/pictures/8859ac67-d1bf-4aff-9d25-1ec8b9922f56.jpg?im_w=720)
Home in Hancock
4.96 out of 5 average rating, 26 reviewsFamily getaway! Private 4 BR Home on Jiminy Peak
![](https://a0.muscache.com/im/pictures/miso/Hosting-1207252900579946402/original/00c3c55c-d480-46a6-9c3c-6a0f48fbba86.jpeg?im_w=720)
Home in Hancock
New place to stayLuxury Mountain Home, Jiminy Peak, Berkshires, MA
Family-friendly, ski-in/ski-out home rentals
![](https://a0.muscache.com/im/pictures/3163a576-4a0a-4143-b4ba-dbc6ac11bf35.jpg?im_w=720)
Guest suite in Lee
4.73 out of 5 average rating, 182 reviewsBerkshire Charm w/ Panoramic views
![](https://a0.muscache.com/im/pictures/7db373a7-09f0-46fb-8f9e-865b6a5ee540.jpg?im_w=720)
Guest suite in Williamsburg
4.82 out of 5 average rating, 11 reviewsFlower Hill Farm Retreat ~ Studio
![](https://a0.muscache.com/im/pictures/miso/Hosting-11338561/original/6f113a7b-b960-48a5-bf48-8a6ac5bf8bb1.jpeg?im_w=720)
Home in Great Barrington
4.69 out of 5 average rating, 118 reviewsMaya's Garden House
![](https://a0.muscache.com/im/pictures/d2274ccd-1511-4c70-951c-d6720bb8db54.jpg?im_w=720)
Condo in Sandwich
4.77 out of 5 average rating, 13 reviews103 N. Shore Blvd # 3 - E. Sandwich beach condo
![](https://a0.muscache.com/im/pictures/89029557/cecd2ad3_original.jpg?im_w=720)
Hotel room in Hancock
4.83 out of 5 average rating, 12 reviewsWyndham Bentley Brook ** 2BR Deluxe
![](https://a0.muscache.com/im/pictures/miso/Hosting-28021171/original/a1ece273-1ae3-48d5-96d0-a2002ef4ec4e.jpeg?im_w=720)
Private room in Becket
Canterbury Farm
![](https://a0.muscache.com/im/pictures/89029557/cecd2ad3_original.jpg?im_w=720)
Hotel room in Hancock
5 out of 5 average rating, 4 reviewsWyndham Bentley Brook * Studio
Ski-in/ski-out condo rentals
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Condo in Hancock
4.91 out of 5 average rating, 54 reviewsJiminy Peak Country Inn - ski in/out condo MT view
![](https://a0.muscache.com/im/pictures/9bf2f3e1-e4a3-4839-bb18-d3a5844cde6f.jpg?im_w=720)
Condo in Hancock
4.94 out of 5 average rating, 17 reviewsLarge one bedroom, two full bath, full kitchen
![](https://a0.muscache.com/im/pictures/miso/Hosting-24713146/original/b1ebde23-5341-48f8-8bca-31ee3223cfd7.jpeg?im_w=720)
Condo in Hancock
4.97 out of 5 average rating, 38 reviewsJiminy's GEM: ski-in/ski-out 3br/3ba condo at base
![](https://a0.muscache.com/im/pictures/miso/Hosting-52670160/original/0cb607f5-2854-4c34-9361-11eadb155cf9.jpeg?im_w=720)
Condo in Hancock
5 out of 5 average rating, 3 reviewsWyndham Bentley Brook
![](https://a0.muscache.com/im/pictures/ae145bdb-32b1-4834-b099-944f3f32a28a.jpg?im_w=720)
Condo in Hancock
4.62 out of 5 average rating, 140 reviewsJiminy Peak Country Inn 1 Bedroom Suite
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-837744814854392086/original/4a77e92f-1e76-40f3-915a-045425bb26a0.jpeg?im_w=720)
Condo in Charlemont
4.77 out of 5 average rating, 13 reviewsBerkshires Getaway < 1 Mi Skiing & Hiking!
![](https://a0.muscache.com/im/pictures/miso/Hosting-729631774173974260/original/9af4ae08-0217-41f9-95b3-0e82a9153105.jpeg?im_w=720)
Condo in Hancock
4.8 out of 5 average rating, 5 reviewsSki-in/Ski-Out on Jiminy Peak
![](https://a0.muscache.com/im/pictures/5513ea0d-d0c1-4995-9f66-08b57ec257e8.jpg?im_w=720)
Condo in Hancock
4.88 out of 5 average rating, 33 reviewsUnique - Country suite @ Jiminy Peak
Destinations to explore
- Ski-in/ski-out rentals United States
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