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Check prices for these dates

Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct
In one month
6 Nov - 8 Nov
In two months
4 Dec - 6 Dec

Our top choices for Middletown guest houses

A bedroom with a bed, a desk, a chair, a TV, a window, and a balcony.

1. Love Shack private retreat

Love Shack private retreat
Middletown
9.4 out of 10, Exceptional, (3 reviews)
"Natural light, high ceilings, ac, good WiFi and tv, great location, thoughtful host. "
United States
Gretchen F.
The price is AU$274
includes taxes & fees
27 Oct - 28 Oct
Love Shack private retreat
A loft bedroom with a bunk bed, a bedside table with a lamp, a TV, and a window with a view.

2. The Well House with outdoor seating and loft!

The Well House with outdoor seating and loft!
Middletown
9.4 out of 10, Exceptional, (3 reviews)
"this was a very neat cozy apartment, perfect location. One block from Main Street in Middletown. Very clean, great host, five star."
United States
louis s.
The price is AU$316
includes taxes & fees
15 Oct - 16 Oct
The Well House with outdoor seating and loft!
A table set with a cheese board, wine glasses, and bottles, with a green sofa and lush greenery in the background.

3. Calderwood Inn

Calderwood Inn
3.5 star property
Healdsburg
9.0 out of 10, Wonderful, (274 reviews)
"Very pleasant stay. So comfortable on the porch and our private patio."
United States
Tom
The price is AU$351
includes taxes & fees
8 Nov - 9 Nov
Calderwood Inn
A house with a tower-like structure, surrounded by a garden with a stone path and a wooden bridge.

4. Okaeri Calistoga

Okaeri Calistoga
5.0 star property
Calistoga
10.0 out of 10, Exceptional, (33 reviews)
"Great stay at a perfectly renovated property with great thoughtfulness around details. Staff (especially Craig) were attentive to any needs and offered great local recommendations. Breakfast was a unique multi-course event which we came to look forward to each morning. Definitely would book again when next in the area."
United States
John
The price is AU$1,051
includes taxes & fees
20 Oct - 21 Oct
Okaeri Calistoga
A bedroom with a large bed, a bedside table with a lamp and a plant, and a window with curtains.

5. Central Santa Rosa Getaway w/ Private Outdoor Space

Central Santa Rosa Getaway w/ Private Outdoor Space
Santa Rosa
8.6 out of 10, Excellent, (15 reviews)
"Great property located on the West side. Very convenient to everything. Very quiet and nice too."
United States
Vance C.
The price is AU$323
includes taxes & fees
19 Oct - 20 Oct
Central Santa Rosa Getaway w/ Private Outdoor Space
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

The Astro

The Astro

10/10 Excellent
"Friendly staff, clean room, easy to find and park, and dog friendly. We only stayed for a night after a long day of travel, and it was overall a great experience."
Lisa 1-night trip
Posted 9 hours ago
The Astro

Find out more about Middletown

Middletown Guest Houses information

Number of reviews
328
Accommodation
11 Guest Houses
Lowest Price
AU$274
Highest Price
AU$1,051