A river flowing through a forest with autumn foliage.

Windsor County Holiday Rentals

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Our top choices for Windsor County holiday rentals

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

1. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
The price is S$226
includes taxes & fees
3 Nov - 4 Nov
Fat Sheep Farm & Cabins
A picnic table and a fire pit by a lake with a forest in the background.

2. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is S$433
includes taxes & fees
23 Oct - 24 Oct
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor County Hotel Reviews

Hotel Coolidge

Hotel Coolidge

10/10 Excellent
"Excellent location! Plan a night at Briggs for a show!!!"
Joy 1-night trip
Posted 4 hours ago
Hotel Coolidge