Middletown Guest Houses

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Guest Houses in Middletown

Calderwood Inn

25 West Grant Street, Healdsburg, CA

$283

includes taxes & fees

$244 per night

Dec 1 - Dec 2

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.

Vineyard Country Inn

201 Main Street, St. Helena, CA

$129

includes taxes & fees

$112 per night

Dec 9 - Dec 10

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.

Charming guest house near Sonoma

$344

includes taxes & fees

$311 per night

Dec 1 - Dec 2

With a stay at this guesthouse in Santa Rosa, you'll be within a 15-minute drive of Graton Resort and Casino and Valley of the Moon Pottery & North Eagle Gallery.

Historic Bed & Breakfast Whole House Rental w Breakfast Included

$1,653

includes taxes & fees

$1,461 per night

Dec 3 - Dec 4

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.

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

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.

Dedicated Patio, Roku & Self Check-In

$217

includes taxes & fees

$202 per night

Nov 23 - Nov 24

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.

Delightful Downtown Cottage House with Modern Amenities (Breakfast Possible)

$1,366

includes taxes & fees

$1,207 per night

Dec 8 - Dec 9

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.

Spacious Honeymoon Suite w/ 2 Beds & Private Kitchen

$499

includes taxes & fees

$440 per night

Dec 1 - Dec 2

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.

Deluxe Suite, Private Patio Overlooking Vineyard & Winery Property

Located in Clearlake Oaks, this guesthouse is within a 15-minute drive of Shannon Ridge Winery and Clear Lake.

Casa Bella

8790 Highway 12, Kenwood, CA

With a stay at Casa Bella in Kenwood, you'll be a 4-minute walk from Chateau St. Jean Winery and 7 minutes by foot from VJB Vineyard & Cellars.

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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.