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Windsor County ski-in/ski-out rentals

We found 549 ski-in/ski-out rentals — enter your dates for availability

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September 2025

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October 2025

Find the best place to stay - Windsor County

living room with fireplace and gorgeous custom details

Luxury Farmhouse Retreat with Jacuzzi, Skate/Swim Pond & AC!

Sleeps 28 · 7 bedrooms · 3+ bathrooms

View of the house from the driveway. On over an acre, surrounded by trees.

"The Crooked House" with A/C and sauna on private wooded lot near Killington

Sleeps 8 · 3 bedrooms · 2+ bathrooms

Located in the Okemo Mt. Community, a mile to the base lodge

Premier Host

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Sleeps 12 · 6 bedrooms · 4 bathrooms

Find spaces that suit your style

Holiday Rental options in Windsor County

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Holiday rentals with pool in Windsor County

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