Windham County rentals with pool

We found 566 rentals with pool — enter your dates for availability

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September 2025

24

October 2025

Explore Windham County rentals with pools

Plenty of private open space to explore with the whole family!

Premier Host

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Sleeps 18 · 5 bedrooms · 3+ bathrooms

Living area

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Sleeps 3 · 2 bedrooms · 2 bathrooms

In the guest house yard.

Premier Host

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Sleeps 30 · 9 bedrooms · 4+ bathrooms

Exterior

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

Sleeps 32 · 12 bedrooms · 12 bathrooms

Find spaces that suit your style

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