Middletown Guest Houses

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Guest Houses in Middletown

Vineyard Country Inn

201 Main Street St. Helena CA

$165 nightly

$190 total

Jan 4 - Jan 5, 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

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

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 12 - Dec 13

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

$1,149 nightly

$1,300 total

Dec 13 - Dec 14

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

$193 nightly

$193 total

Jan 7 - Jan 8, 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

Love Shack private retreat

Middletown CA

$209 nightly

$230 total

Jan 3 - Jan 4, 2026

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

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

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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.