Windsor County pet-friendly rentals

We found 720 pet-friendly rentals — enter your dates for availability

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September 2025

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October 2025

Explore Windsor County pet-friendly rentals

living room with fireplace and gorgeous custom details

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

Sleeps 28 · 7 bedrooms · 3+ 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

Come back to a cozy fire after a long day of skiing. ⛷️

Premier Host

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Sleeps 7 · 3 bedrooms · 1+ bathroom

Find spaces that suit your style

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Holiday Rental options in Windsor County

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