A stone bridge over a calm river, a historic tower, and illuminated buildings at dusk.

Windsor cottages

We found 52 cottages — enter your dates for availability

Explore Windsor cottage rentals

Image of Chalk Hill Healdsburg new pool cottage. Sleeps 4 on 6 acres with sweeping views!

Chalk Hill Healdsburg new pool cottage. Sleeps 4 on 6 acres with sweeping views!

Sleeps 4 · 1 bedroom · 2 bathrooms

Image of Vineyard Cottage w/ Fire Pit | Chalk Hill Wine Country

Premier Host

Vineyard Cottage w/ Fire Pit | Chalk Hill Wine Country

Sleeps 4 · 1 bedroom · 1 bathroom

Image of Enjoy a Slice Of Country--Two miles to Downtown Healdsburg

Enjoy a Slice Of Country--Two miles to Downtown Healdsburg

Sleeps 4 · 2 bedrooms · 1 bathroom

Image of 1 Bedroom Cottage Walking Distance to Down Town

Premier Host

1 Bedroom Cottage Walking Distance to Down Town

Sleeps 3 · 2 bedrooms · 1 bathroom

Image of Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

Sleeps 6 · 3 bedrooms · 2 bathrooms

Image of Tranquil cottage just a short walk to the Russian River in Guerneville

Tranquil cottage just a short walk to the Russian River in Guerneville

Sleeps 4 · 1 bedroom · 1 bathroom

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