Photo by Shannon Willitts

Search Guest Houses in Middletown

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Compare 12 Guest Houses in Middletown with updated reviews, rates, and availability.

Vineyard Country Inn

3.5 star property
9.2 out of 10, Wonderful, (620)
"Great location, close to downtown St. Helena and wineries. "
The price is SAR 731
SAR 841 total
includes taxes & fees
6 Apr - 7 Apr
Vineyard Country Inn

Calderwood Inn

3.5 star property
9.2 out of 10, Wonderful, (231)
"Very Nice. Friendly people."
The price is SAR 756
SAR 877 total
includes taxes & fees
14 Apr - 15 Apr
Calderwood Inn

Spacious Honeymoon Suite w/ 2 Beds & Private Kitchen

10.0 out of 10, Exceptional, (20)
"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. "
The price is SAR 1,107
SAR 2,148 total
includes taxes & fees
1 Apr - 2 Apr
Spacious Honeymoon Suite w/ 2 Beds & Private Kitchen

Charming guest house near Sonoma

9.6 out of 10, Exceptional, (20)
"We stayed here to celebrate our 6 year anniversary. It’s a beautiful property and had a wonderful time. The hot tub was a great addition. The kitchen was very helpful to make our own dinner & grilled our steaks outside. Would definitely stay here again! 10/10 experience."
The price is SAR 638
SAR 1,286 total
includes taxes & fees
6 Apr - 7 Apr
Charming guest house near Sonoma

Bunkhouse at Side Road Farm charming one bedroom cottage

9.8 out of 10, Exceptional, (47)
"My husband and I thoroughly enjoyed our three-night stay in the bunkhouse in early March. Suzanne is a very generous and welcoming host -- thank you again for the delicious bottle of sauvignon blanc and other goodies! Communications with Suzanne were always clear and timely. The bunkhouse is very comfortable for a couple, with nice linens on the bed, plentiful towels in the bath, plenty of coffee for the morning. The location is perfect for exploring the beautiful Sonoma wine-country. We would...
Bunkhouse at Side Road Farm charming one bedroom cottage

Vignoble House St. Helena/Napa Valley

9.8 out of 10, Exceptional, (17)
"Great house in all the important ways but a few annoying glitches. The instruction book had 8 pages on the rules of bocce ball and zero on how to use the TV (which we never figured out how to use) or how to use the coffee machine (also never figured that out). Basketball hoop was a big plus for my son-in-law but all the basketballs were flat and we were told to find the pump (which we never found). Nice to have a peloton bike but it wasn’t connected to the internet. Little annoying stuff like...
Vignoble House St. Helena/Napa Valley

Delightful Downtown Cottage House with Modern Amenities (Breakfast Possible)

9.6 out of 10, Exceptional, (23)
"Lovely shabby chic vibe in the most charming setting possible, loved each moment!"
The price is SAR 2,462
SAR 4,821 total
includes taxes & fees
1 Apr - 2 Apr
Delightful Downtown Cottage House with Modern Amenities (Breakfast Possible)

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

9.0 out of 10, Wonderful, (82)
"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

Dedicated Patio, Roku & Self Check-In

8.4 out of 10, Very Good, (11)
"This is the second time that I Stayed at the Ridley suites. it is convenient , clean And the property manager responds quickly"
Dedicated Patio, Roku & Self Check-In

Deluxe Suite, Private Patio Overlooking Vineyard & Winery Property

The price is SAR 1,467
SAR 1,820 total
includes taxes & fees
1 Apr - 2 Apr
Deluxe Suite, Private Patio Overlooking Vineyard & Winery Property

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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Other property types in Middletown

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (42)
"The Backyard Garden Oasis was quiet and secluded. We enjoyed walking along the quiet street in the morning. The owner is a helpful host. "
The price is SAR 728
SAR 811 total
includes taxes & fees
1 Apr - 2 Apr
Backyard Garden Oasis

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (295)
"It was clean, quiet and all requirements met. "
The price is SAR 485
SAR 541 total
includes taxes & fees
6 Apr - 7 Apr
Clear Lake Cottages & Marina

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

10.0 out of 10, Exceptional, (220)
"This is our second time renting Willian's home in Kenwood. This home is absolutely stunning and fully equipped with everything you need for a family or group of friends gathering. Fold-out bunk beds, 3 pack and plays, a high chair, tennis and pickle ball rackets, sidewalk chalk and great kitchen and bathroom products. Linens are great quality as well. Chateau St Jean and many other wineries are minutes away. We will absolutely rent this home again and will recommend it to others.Only issue is...
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
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.