Windsor Guest Houses

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Guest Houses in Windsor

Glen Ellen Inn

13670 Arnold Dr Glen Ellen CA

$165 nightly

$188 total

Oct 21 - Oct 22

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

Located in Glen Ellen, Glen Ellen Inn is in a rural location, within a 5-minute walk of Talisman Wines and Wine Snob.

Parking included

Free WiFi

Okaeri Calistoga

1415 Foothill Blvd Calistoga CA

$605 nightly

$696 total

Oct 21 - Oct 22

Total with taxes and fees

With a stay at Okaeri Calistoga in Calistoga, you'll be a 1-minute drive from Calistoga Hot Springs and 5 minutes from Castello di Amorosa.

Breakfast included

Parking included

Calderwood Inn

25 West Grant Street Healdsburg CA

$181 nightly

$210 total

Nov 9 - Nov 10

Total with taxes and fees

With a stay at Calderwood Inn in Healdsburg, you'll be within a 5-minute drive of Russian River and Seghesio Family Vineyards.

Breakfast included

Pet friendly

Guerneville Lodge

15905 River Road Guerneville CA

$129 nightly

$147 total

Nov 12 - Nov 13

Total with taxes and fees

When you stay at Guerneville Lodge in Guerneville, you'll be on a river, just steps from Russian River and 9 minutes by foot from Pee Wee Golf and Arcade.

Hot Tub

Free WiFi

Vineyard Country Inn

201 Main Street St. Helena CA

Located in St. Helena (Thoman), Vineyard Country Inn is a 4-minute walk from Salvestrin Winery and 13 minutes by foot from HALL St. Helena Winery.

Pool

Breakfast included

Bunkhouse at Side Road Farm charming one bedroom cottage

Healdsburg CA

With a stay at this guesthouse, you'll be centrally located in Healdsburg, within a 10-minute drive of Russian River and Matrix Winery.

Free WiFi

Air conditioning

Escape to Sebastopol's charm, near The Barlow. We love Dogs!

Sebastopol CA

Located in Sebastopol, this guesthouse is in a rural location, within a 5-minute drive of Patrick Amiot Junk Art and West County Museum.

Pet friendly

Free WiFi

Wine Country Retreat w Pool & Spa - Near Vineyards

Santa Rosa CA

Located in Santa Rosa, this guesthouse is in a rural location, within a 5-minute drive of Bennett Valley Golf Course and Sonoma County Fairgrounds.

Pool

Hot Tub

Central Santa Rosa Getaway w/ Private Outdoor Space

Santa Rosa CA

$206 nightly

$222 total

Oct 21 - Oct 22

Total with taxes and fees

With a stay at this guesthouse in Santa Rosa, you'll be within a 10-minute drive of Graton Resort and Casino and Redwood Empire Ice Arena.

The Well House with outdoor seating and loft!

Middletown CA

$201 nightly

$201 total

Nov 1 - Nov 2

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

Love Shack private retreat

Middletown CA

$189 nightly

$189 total

Oct 21 - Oct 22

Total with taxes and fees

Located in Middletown, this guesthouse is within a 5-minute drive of Rabbit Hill Preserve and Beaver Creek Vineyards.

Air conditioning

Parking available

Daisy's Guest House

13373 Frati Lane Sebastopol CA

Located in Sebastopol, Daisy's Guest House is within a 10-minute drive of Occidental Arts and Ecology Center and Marimar Estate Vineyard.

Breakfast included

Parking included

Don't see what you're looking for?

See all available properties in Windsor

View all properties

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.