Ski-in/Ski-out holiday rentals in Massachusetts
Find and book unique ski-in/out homes on Airbnb
Top-rated ski-in/out rentals in Massachusetts
Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Massachusetts ski-in/out rentals
Ski-in/out house rentals
Home in Hancock
4.8 out of 5 average rating, 10 reviewsBeautiful 4 Bedroom Townhouse in the Berkshires
Home in Monterey
Smiling Dog Meadow
Home in Hancock
4.95 out of 5 average rating, 19 reviewsCondo on the mountain
Home in Westminster
4.89 out of 5 average rating, 149 reviewsLakefront; view of ski mtn, firepit, dock, kayaks
Home in Worthington
4.67 out of 5 average rating, 9 reviewsA simple kind of paradise
Home in Hancock
4.9 out of 5 average rating, 20 reviewsAutumn at Left Bank Lodge
Home in Hancock
4.96 out of 5 average rating, 26 reviewsFamily getaway! Private 4 BR Home on Jiminy Peak
Home in Stockbridge
Historic Stockbridge Home on Golf Course
Family-friendly, ski-in/out home rentals
Hotel room in Hancock
4.83 out of 5 average rating, 12 reviewsWyndham Bentley Brook ** 2BR Deluxe
Guest suite in Williamsburg
4.82 out of 5 average rating, 11 reviewsFlower Hill Farm Retreat ~ Studio
Hotel room in Hancock
5 out of 5 average rating, 4 reviewsWyndham Bentley Brook * Studio
Private room in Becket
Canterbury Farm
Home in Hawley
4.97 out of 5 average rating, 36 reviewsStump Sprouts Lodge
Home in Manchester-by-the-Sea
4.75 out of 5 average rating, 4 reviewsCountry Estate, Heated Pool, near beach
Ski-in/out apartment rentals
Apartment in Hancock
5 out of 5 average rating, 6 reviewsCondo Resort at Jiminy Peak Ski Mountain's Base
Apartment in Hancock
4.98 out of 5 average rating, 42 reviewsJiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Apartment in Hancock
4.88 out of 5 average rating, 33 reviewsUnique - Country suite @ Jiminy Peak
Apartment in Woburn
New place to stayPlatinum Apartment
Apartment in Hancock
4.89 out of 5 average rating, 27 reviewsJiminy Peak Apartment
Apartment in Hancock
4.62 out of 5 average rating, 143 reviewsJiminy Peak Country Inn 1 Bedroom Suite
Apartment in Hancock
4.91 out of 5 average rating, 54 reviewsJiminy Peak Country Inn - ski in/out condo MT view
Apartment in Hancock
4.8 out of 5 average rating, 5 reviewsSki-in/Ski-Out on Jiminy Peak
Destinations to explore
- Ski-in/ski-out rentals United States
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- Yurt Rentals United States
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- Things to do Massachusetts
- Food and drink Massachusetts
- Art and culture Massachusetts
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- Nature and outdoors Massachusetts
- Sports activities Massachusetts