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Check prices for these dates

Next weekend
26 Sept - 28 Sept
In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov

Featured Guest Houses in Middletown and around

Vineyard Country Inn
Property grounds

Vineyard Country Inn

3.5 star property
9.2 out of 10, Wonderful, (699)
"We absolutely loved this property! "
The price is €268
includes taxes & fees
24 Sept - 25 Sept
Vineyard Country Inn
Calderwood Inn
Executive Room, 1 King Bed | Terrace/patio

Calderwood Inn

3.5 star property
9.2 out of 10, Wonderful, (240)
"Lovely historic house, conveniently located close to the square. The staff was very helpful and the breakfast was delicious."
The price is €281
includes taxes & fees
12 Oct - 13 Oct
Calderwood Inn
Sonoma County stunner near wineries & parks with hot tub & garden - walkable
Outdoor spa tub

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

9.0 out of 10, Wonderful, (85)
"Had a great stay at Bruce’s. Nice place for 2 people. Located close to everything. Hot Tub is a plus. Would definitely stay again."
Sonoma County stunner near wineries & parks with hot tub & garden - walkable
Delightful Downtown Cottage House with Modern Amenities (Breakfast Possible)
Exterior

Delightful Downtown Cottage House with Modern Amenities (Breakfast Possible)

9.6 out of 10, Exceptional, (23)
"Great location! Property needs updating. Manager needs better customer service. "
Delightful Downtown Cottage House with Modern Amenities (Breakfast Possible)
Charming guest house near Sonoma
Terrace/patio

Charming guest house near Sonoma

9.6 out of 10, Exceptional, (29)
"Nicely appointed, quiet, great location!"
Charming guest house near Sonoma
Spacious Honeymoon Suite w/ 2 Beds & Private Kitchen
Outdoor dining

Spacious Honeymoon Suite w/ 2 Beds & Private Kitchen

10.0 out of 10, Exceptional, (21)
"We had an outstanding time staying in St Helena am most importantly in this beautiful villa at the Inn of St Helena. Totally private and serene. This was a perfect place to stay to kick off my birthday trip. I hope we can come back. "
Spacious Honeymoon Suite w/ 2 Beds & Private Kitchen
Historic Bed & Breakfast Whole House Rental w Breakfast Included
5 bedrooms, iron/ironing board, travel cot, WiFi

Historic Bed & Breakfast Whole House Rental w Breakfast Included

9.8 out of 10, Exceptional, (26)
"Welcoming and comfortable "
Historic Bed & Breakfast Whole House Rental w Breakfast Included
Vignoble House St. Helena/Napa Valley
Outdoor pool, a heated pool

Vignoble House St. Helena/Napa Valley

9.8 out of 10, Exceptional, (18)
"The property was perfect for the five couples that were part of our group, including, for example, en suite bathrooms for each bedroom. Also, outdoor access for the two lower-level bedrooms was helpful and utilized frequently. The pool area is amazing as well as the outdoor seating and deck spaces. Everyone enjoyed the chickens and the fresh eggs every morning, what a treat. The location of the property is ideal being in close proximity to Saint Helena, making it easy to get to other areas of...
Vignoble House St. Helena/Napa Valley
Love Shack private retreat
Property grounds

Love Shack private retreat

9.0 out of 10, Wonderful, (2)
"Natural light, high ceilings, ac, good WiFi and tv, great location, thoughtful host. "
Love Shack private retreat
Bunkhouse at Side Road Farm charming one bedroom cottage
Property grounds

Bunkhouse at Side Road Farm charming one bedroom cottage

9.8 out of 10, Exceptional, (54)
"Had a nice stay at the bunkhouse. Sue added in many nice amenities. It was just what we needed for our stay in the area. Clean, comfortable and easy to get to from Healdsburg. "
Bunkhouse at Side Road Farm charming one bedroom cottage
Dedicated Patio, Roku & Self Check-In
1 bedroom, desk, WiFi

Dedicated Patio, Roku & Self Check-In

8.8 out of 10, Excellent, (13)
"Great property located on the West side. Very convenient to everything. Very quiet and nice too."
Dedicated Patio, Roku & Self Check-In
The Well House with outdoor seating and loft!
Property grounds

The Well House with outdoor seating and loft!

"I didn't see it explicitly stated that the bedroom and kitchen-bathroom areas are separated by a shaded porch. It may not be a big deal to some, but we stayed during 100F weather, so having to step out of the air-conditioned space was not ideal. Additionally, the kitchen-bathroom area is not air-conditioned, so it was like an oven in there while trying to cook meals. Finally, the water pressure in the shower was very low. I rated the surrounding area as OK because it was really hot and dusty. It...
The Well House with outdoor seating and loft!
Wine Country Retreat w Pool & Spa - Near Vineyards
Terrace/patio

Wine Country Retreat w Pool & Spa - Near Vineyards

10.0 out of 10, Exceptional, (15)
"Wonderful host and property. Perfect stay for the weekend with every amenity you could think of! "
Wine Country Retreat w Pool & Spa - Near Vineyards
Casa Bella
Sun deck

Casa Bella

3.0 star property
9.8 out of 10, Exceptional, (24)
"Great Bed and Breakfast, friendly staff"
Casa Bella
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.
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Top Middletown Hotel Reviews

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

10/10 Excellent
"Wonderful stop on our trip. No need to be apprehensive making a reservation here. "
Leon 1-night trip
Posted 2 days ago
Holiday Inn Express® Windsor Sonoma Wine Country by IHG

Find out more about Middletown

Find out more about Middletown

Middletown Guest Houses information

Number of reviews
1,139
Accommodation
14 Guest Houses
Lowest Price
€268
Highest Price
€281

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