A red covered bridge over a calm river, surrounded by lush greenery and trees.

Winterset farm rentals

We found 1 farm rentals — enter your dates for availability

Find the best place to stay - Winterset

Image of Charming Winterset Vacation Rental w/ Yard & Patio

Premier Host

Charming Winterset Vacation Rental w/ Yard & Patio

Sleeps 8 · 4 bedrooms · 1+ bathroom

Image of Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Premier Host

Covered Bridge Haven - 3-bedroom house with themed rooms in Winterset

Sleeps 10 · 3 bedrooms · 3 bathrooms

Image of The Little Brick House - Walkable to the Square Dining & Shopping

Premier Host

The Little Brick House - Walkable to the Square Dining & Shopping

Sleeps 4 · 2 bedrooms · 1+ bathroom

Image of Modern home on acreage with pond, trails, rolling hills, and sunset views

Modern home on acreage with pond, trails, rolling hills, and sunset views

Sleeps 6 · 2 bedrooms · 2 bathrooms

Image of Renovated Cottage on Court: 3 blocks to historic downtown square

Premier Host

Renovated Cottage on Court: 3 blocks to historic downtown square

Sleeps 6 · 2 bedrooms · 1+ bathroom

Image of Holliwell Bridge Retreat - Private, Spacious & Close to town! Great for Groups!

Premier Host

Holliwell Bridge Retreat - Private, Spacious & Close to town! Great for Groups!

Sleeps 12 · 5 bedrooms · 2+ bathrooms

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Enjoy full kitchens, laundry, pools, gardens and more
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More space, more privacy, more amenities — more value