Windsor Guest Houses

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Guest Houses in Windsor

Vineyard Country Inn

201 Main Street St. Helena CA

$158 nightly

$182 total

Jan 13 - Jan 14, 2026

Total with taxes and fees

Located in St. Helena, Vineyard Country Inn is in the historical district, a 4-minute walk from Salvestrin Winery and 12 minutes by foot from HALL St. Helena Winery.

Pool

Breakfast included

Guerneville Lodge

15905 River Road Guerneville CA

$149 nightly

$170 total

Dec 18 - Dec 19

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

With a stay at Guerneville Lodge in Guerneville, you'll be on a river, just a 1-minute walk from Russian River and 9 minutes by foot from Pee Wee Golf and Arcade.

Hot Tub

Free WiFi

Calderwood Inn

25 West Grant Street Healdsburg CA

$181 nightly

$210 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at Calderwood Inn in Healdsburg, you'll be within a 10-minute walk of Seghesio Family Vineyards and Raven Performing Arts Theater.

Breakfast included

Pet friendly

Quiet, Cozy, Russian River Retreat in the Redwoods. Private Garden View Unit

Guerneville CA

$253 nightly

$280 total

Dec 14 - Dec 15

Total with taxes and fees

When you stay at this guesthouse in Guerneville, you'll be by the sea, within a 5-minute drive of Russian River and Pee Wee Golf and Arcade.

Pet friendly

Free WiFi

Charming guest house near Sonoma

Santa Rosa CA

$310 nightly

$349 total

Dec 15 - Dec 16

Total with taxes and fees

With a stay at this guesthouse in Santa Rosa, you'll be within a 15-minute drive of Graton Resort and Casino and Rincon Valley Community Park Dog Park.

Hot Tub

Pet friendly

Sonoma County stunner near wineries & parks with hot tub & garden - walkable

Santa Rosa CA

With a stay at this guesthouse in Santa Rosa, you'll be within a 15-minute drive of Graton Resort and Casino and Spring Lake Park.

Hot Tub

Air conditioning

Historic Bed & Breakfast Whole House Rental w Breakfast Included

Saint Helena CA

$1,513 nightly

$1,716 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this guesthouse, you'll be centrally located in St. Helena, within a 15-minute drive of Castello di Amorosa and Calistoga Hot Springs.

Hot Tub

Air conditioning

Spacious Honeymoon Suite w/ 2 Beds & Private Kitchen

Saint Helena CA

$509 nightly

$576 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this guesthouse, you'll be centrally located in St. Helena, within a 15-minute drive of Castello di Amorosa and Calistoga Hot Springs.

Hot Tub

Air conditioning

Delightful Downtown Cottage House with Modern Amenities (Breakfast Possible)

St. Helena CA

$1,077 nightly

$1,228 total

Dec 16 - Dec 17

Total with taxes and fees

With a stay at this guesthouse, you'll be centrally located in St. Helena, within a 15-minute drive of Castello di Amorosa and Calistoga Hot Springs.

Hot Tub

Air conditioning

Vignoble House St. Helena/Napa Valley

St. Helena CA

With a stay at this guesthouse in St. Helena, you'll be within a 15-minute drive of Castello di Amorosa and Calistoga Hot Springs.

Pool

Hot Tub

The Well House with outdoor seating and loft!

Middletown CA

$205 nightly

$205 total

Jan 3 - Jan 4, 2026

Total with taxes and fees

With a stay at this guesthouse in Middletown, you'll be within a 5-minute drive of Rabbit Hill Preserve and Beaver Creek Vineyards.

Air conditioning

Parking available

Bunkhouse at Side Road Farm charming one bedroom cottage

Healdsburg CA

A stay at this guesthouse places you in the heart of Healdsburg, just a 3-minute walk from Matrix Winery and within a 5-minute drive of Flowers Vineyards and Winery.

Free WiFi

Air conditioning

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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.