Ski-in/Ski-out vacation rentals in Berkshire County
Find and book unique ski-in/ski-out homes on Airbnb
Top-rated ski-in/ski-out rentals in Berkshire County
Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Berkshire County ski-in/ski-out rentals
Ski-in/ski-out house rentals
Home in Hancock
5.0 out of 5 average rating, 24 reviewsCozy Cabin in Berkshires Resort Property
Home in Hancock
4.75 out of 5 average rating, 8 reviewsBeautiful 4 Bedroom Townhouse in the Berkshires
Home in Stephentown
4.8 out of 5 average rating, 65 reviewsA Magic Spot: Booking year round.
Home in Hancock
4.95 out of 5 average rating, 19 reviewsMountainside: Large 3-level Jiminy Peak Home
Home in Worthington
4.67 out of 5 average rating, 9 reviewsA simple kind of paradise
Home in Hancock
5.0 out of 5 average rating, 10 reviewsSki-in, Ski-out 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 Canaan
5.0 out of 5 average rating, 11 reviewsKnoll Rock House (3B/3B) - Best of the Berkshires
Family-friendly, ski-in/ski-out home rentals
Home in Hawley
4.97 out of 5 average rating, 33 reviewsStump Sprouts Lodge
Hotel room in Hancock
4.83 out of 5 average rating, 12 reviewsWyndham Bentley Brook ** 2BR Deluxe
Room in Sandisfield
4.92 out of 5 average rating, 133 reviewsHospitality in the Berkshire Woods
Room in Becket
Canterbury Farm
Hotel room in Hancock
5.0 out of 5 average rating, 4 reviewsWyndham Bentley Brook * Studio
Ski-in/ski-out condo rentals
Condo in Hancock
4.88 out of 5 average rating, 33 reviewsUnique - Country suite @ Jiminy Peak
Condo in Hancock
4.62 out of 5 average rating, 138 reviewsJiminy Peak Country Inn 1 Bedroom Suite
Condo in Hancock
4.8 out of 5 average rating, 5 reviewsSki-in/Ski-Out on Jiminy Peak
Condo in Hancock
5.0 out of 5 average rating, 3 reviewsBentley Brook Presidents Week & Christmas
Condo in Hancock
Condo Resort at Jiminy Peak Ski Mountain's Base
Condo in Hancock
4.93 out of 5 average rating, 58 reviewsSKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1
Condo in Hancock
4.93 out of 5 average rating, 15 reviewsLarge one bedroom, two full bath, full kitchen
Condo in Hancock
Condo Resort at Jiminy Peak Ski Mountain's Base
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