Middletown 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 Middletown

Calderwood Inn

25 West Grant Street, Healdsburg, CA

$240

includes taxes & fees

$207 per night

Dec 5 - Dec 6

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

$136

includes taxes & fees

$118 per night

Nov 11 - Nov 12

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

Nov 17 - Nov 18

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.

Historic Bed & Breakfast Whole House Rental w Breakfast Included

$1,951

includes taxes & fees

$1,724 per night

Dec 4 - Dec 5

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

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

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)

$1,369

includes taxes & fees

$1,210 per night

Nov 6 - Nov 7

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

$501

includes taxes & fees

$442 per night

Nov 17 - Nov 18

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

$486

includes taxes & fees

$445 per night

Nov 6 - Nov 7

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.

Don't see what you're looking for?

See all available properties in Middletown

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.