Ski-in/Ski-out holiday rentals in Western Massachusetts
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Top-rated ski-in/out rentals in Western 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 Western Massachusetts ski-in/out rentals
Ski-in/out house rentals
Home in Westminster
4.87 out of 5 average rating, 123 reviewsLakefront; view of ski mtn, firepit, dock, kayaks
Home in Otis
4.92 out of 5 average rating, 131 reviewsThe Pinnacle House at Otis Ridge Ski Area!
Home in Winhall
4.94 out of 5 average rating, 109 reviewsBeautiful Stratton-Manchester VT Retreat w/hot tub
Home in Phoenicia
4.94 out of 5 average rating, 144 reviewsHeart of Phoenicia: Serene. Cozy. Close To All!
Home in Ashfield
5.0 out of 5 average rating, 78 reviewsSunny Chalet Nestled in the Woods of Ashfield
Home in Hancock
5.0 out of 5 average rating, 5 reviewsBougie B's Mountainside Getaway
Home in New Hartford
4.92 out of 5 average rating, 12 reviewsMountain Serenity Lake View Pool & Hot Tub
Home in Plymouth
5.0 out of 5 average rating, 16 reviewsLakefront Serenity Getaway: Your Blissful Escape
Family-friendly, ski-in/out home rentals
Cottage in Hollis
4.87 out of 5 average rating, 210 reviewsLakefront Nature Getaway - Wood fired Cedar Sauna
Apartment in Hunter
4.87 out of 5 average rating, 254 reviewsMountainside Haven - walk to Hunter Mtn!
Apartment in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
Apartment in Ludlow
4.95 out of 5 average rating, 110 reviewsSlopeside condo at the base of Okemo-steps to lift
Home in hunter
4.82 out of 5 average rating, 179 reviewsCozy 3 bedroom summer winter home
Apartment in West Kill
4.85 out of 5 average rating, 131 reviewsTrailside At Hunter-Phase II-Hunter NY
Guest suite in Lee
4.72 out of 5 average rating, 176 reviewsBerkshire Charm w/ Panoramic views
Home in Cavendish
5.0 out of 5 average rating, 99 reviewsMidcentury Hillside Retreat - Summer Paradise
Ski-in/out cabin rentals
Cabin in Woodford
4.98 out of 5 average rating, 139 reviewsStone's Camp on Stamford Stream
Cabin in Londonderry
4.84 out of 5 average rating, 57 reviewsModern Magic Ski Chalet: Central to 4 Mountains
Cabin in Hunter
4.92 out of 5 average rating, 13 reviewsMaple’s Cabin
Cabin in Hunter
5.0 out of 5 average rating, 79 reviewsBest rated cabin in Hunter cozy 4 bedrms 3 baths
Cabin in Hunter
4.89 out of 5 average rating, 56 reviews4BR ski on ski off Hunter Mountain Condo
Cabin in Hunter
5.0 out of 5 average rating, 5 reviewsThe Riverside
Cabin in Vernon
4.94 out of 5 average rating, 51 reviewsCozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Cabin in Shandaken
4.65 out of 5 average rating, 17 reviews2BR Hunter Mountain A-Frame. Walk to ski lifts!
Destinations to explore
- Cambridge Holiday rentals
- New Haven Holiday rentals
- Lake George Holiday rentals
- Providence Holiday rentals
- Catskill Holiday rentals
- Albany Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Montreal Holiday rentals
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