Weston showing interior views

Windsor County rentals with pool

We found 891 rentals with pool — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

September 2025

14

October 2025

Explore Windsor County rentals with pools

Enter the home to an open living space

Premier Host

Beautifully renovated with fireplace and coffee bar

Sleeps 6 · 2 bedrooms · 1+ bathroom

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

Find spaces that suit your style

Holiday Rental options in Windsor County

Oceanfront holiday rentals in Windsor County

Lake holiday rentals in Windsor County

Monthly rentals in Windsor County

Family-friendly holiday rentals in Windsor County

Ski holiday rentals in Windsor County

Beach holiday rentals in Windsor County

Pet-friendly holiday rentals in Windsor County

Mountain holiday rentals in Windsor County

Holiday rentals with spa pool in Windsor County

db484733-e4f5-c20f-d041-b2acf6fef38fb4ba5548-e544-491d-9f6c-700141ca6506