Windsor County rentals with pool

We found 892 rentals with pool — enter your dates for availability

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September 2025

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October 2025

Explore Windsor County rentals with pools

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

New standing steam roof!

Premier Host

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Sleeps 10 · 3 bedrooms · 2 bathrooms

yard near pool

LEAF PEEPING OASIS Hot Tub Sauna Pool Table Ping Pong Fire Pit Wood Stove

Sleeps 5 · 3 bedrooms · 2 bathrooms

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