A calm river with clear water, surrounded by dense greenery and trees.

Search Guest Houses in Middletown from CA $263

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Sep 25 - Sep 27
In two weeks
Oct 2 - Oct 4
In one month
Oct 16 - Oct 18
In two months
Nov 13 - Nov 15

Our top choices for Middletown guest houses

1 bedroom, internet, bed sheets

1. 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 Well House with outdoor seating and loft!
1 bedroom, desk, iron/ironing board, WiFi

2. 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 CA $122
CA $263 total
includes taxes & fees
Sep 20 - Sep 21
Love Shack private retreat
Exterior

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 CA $345
CA $400 total
includes taxes & fees
Sep 21 - Sep 22
Calderwood Inn
1 bedroom, desk, WiFi

4. 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 CA $183
CA $310 total
includes taxes & fees
Oct 1 - Oct 2
Central Santa Rosa Getaway w/ Private Outdoor Space
Exterior detail

5. Charming guest house near Sonoma

Charming guest house near Sonoma
Santa Rosa
9.8 out of 10, Exceptional, (32 reviews)
"Very nice private space with a great host"
United States
Bob H.
The price is CA $350
CA $628 total
includes taxes & fees
Sep 27 - Sep 28
Charming guest house near Sonoma
Front of property

6. Okaeri Calistoga

Okaeri Calistoga
5.0 star property
Calistoga
10.0 out of 10, Exceptional, (32 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 CA $831
CA $955 total
includes taxes & fees
Sep 21 - Sep 22
Okaeri Calistoga
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Hotel La Rose

Hotel La Rose

10/10 Excellent
"Celeste at the front desk informed me that the elevator was not working. My room was on the fourth floor. She went out of her way and put me in one of the carriage houses across the street. I have to say it’s one of the nicest hotel rooms I’ve ever stayed in, and Celeste went above and beyond to make sure I was taken care of. Should I ever be in Santa Rosa again, I will not hesitate to book a room here. Thank you so much…."
Thomas 1-night trip
Posted 1 hour ago
Hotel La Rose

Find out more about Middletown

Middletown Guest Houses information

Number of reviews
359
Accommodation
11 Guest Houses
Lowest Price
CA $263
Highest Price
CA $955

Explore a world of travel with Expedia