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

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

Our top choices for Middletown bed & breakfast

A dining area with a large table and chairs, a glass enclosure, and a view of the garden outside.

1. Calistoga Wine Way Inn

Calistoga Wine Way Inn
3.0 star property
Calistoga
8.8 out of 10, Excellent, (647 reviews)
"Enjoyed our stay"
United States
Pavel
$203 nightly
The price is $234
Sep 29 - Sep 30
Total with taxes and fees
Calistoga Wine Way Inn
A landscaped garden with a pathway leading to a building with a green roof and stone columns.

2. Thorn Hill Vineyard Villas

Thorn Hill Vineyard Villas
3.5 star property
Lower Lake
8.8 out of 10, Excellent, (31 reviews)
"Beautiful location and reasonably priced for luxury accommodations."
United States
Evan
$224 nightly
The price is $250
Sep 28 - Sep 29
Total with taxes and fees
Thorn Hill Vineyard Villas
A house with a porch, potted plants, and a brick wall.

3. Bear Flag Inn

Bear Flag Inn
3.0 star property
Calistoga
9.4 out of 10, Exceptional, (125 reviews)
"The breakfast was delicious and they had a little wine happy hour for the guests. Our stay felt very homey."
United States
Jacob
$249 nightly
The price is $286
Sep 27 - Sep 28
Total with taxes and fees
Bear Flag Inn
A patio with outdoor furniture, a stone table, and a view of vineyards and mountains.

4. Chateau De Vie

Chateau De Vie
3.0 star property
Calistoga
9.8 out of 10, Exceptional, (51 reviews)
"We enjoyed our stay."
United States
Bruce
$441 nightly
The price is $508
Oct 4 - Oct 5
Total with taxes and fees
Chateau De Vie
A historic building with a well-maintained facade, a prominent sign indicating 'Embrace California 128', and a flagpole with an American flag.

5. Embrace Calistoga

Embrace Calistoga
3.5 star property
Calistoga
10.0 out of 10, Exceptional, (57 reviews)
"Chris and Brent were wonderful hosts and made our stay so enjoyable. The multi course breakfast on Saturday and Sunday was amazing! We were celebrating a birthday and they even had a cake complete with candle for us. Every evening was a different cheese plate and wine on the veranda - we felt so special. We can’t wait to visit again and can’t recommend Embrace Calistoga more highly."
United States
Melanie
$329 nightly
The price is $378
Sep 27 - Sep 28
Total with taxes and fees
Embrace Calistoga
An outdoor patio with a wooden deck, two wooden chairs, a table, and a large vase.

6. Grape Leaf Inn

Grape Leaf Inn
4.0 star property
Healdsburg
9.4 out of 10, Exceptional, (177 reviews)
"Just a beautiful property a home away from home!! Highly recommend!!"
United States
Anthony
$268 nightly
The price is $311
Sep 28 - Sep 29
Total with taxes and fees
Grape Leaf Inn
A garden pathway leading to a white building with a traditional design, surrounded by neatly trimmed hedges and a white picket fence.

7. Inn St Helena

Inn St Helena
3.0 star property
Downtown St. Helena
9.6 out of 10, Exceptional, (164 reviews)
"The property was perfect and located walking distance to downtown. We will be back."
United States
Danny
$291 nightly
The price is $335
Sep 30 - Oct 1
Total with taxes and fees
Inn St Helena
A stone cabin with a pond in front, illuminated by string lights.

8. Bed & Barrel at Stonehouse Cellars

Bed & Barrel at Stonehouse Cellars
4.0 star property
Clearlake Oaks
9.2 out of 10, Wonderful, (60 reviews)
"Excellent stay- hidden gem"
United States
Anshuman
$299 nightly
The price is $333
Oct 26 - Oct 27
Total with taxes and fees
Bed & Barrel at Stonehouse Cellars
A modern interior with a staircase, a large window with reflections, and a seating area.

9. Healdsburg Inn on the Plaza, A Four Sisters Inn

Healdsburg Inn on the Plaza, A Four Sisters Inn
3.5 star property
Healdsburg
8.6 out of 10, Excellent, (616 reviews)
"Everything about this stay was perfection. We couldn’t ask for a better stay. We will return and recommend to friends and family."
United States
Victoria
$319 nightly
The price is $371
Sep 27 - Sep 28
Total with taxes and fees
Healdsburg Inn on the Plaza, A Four Sisters Inn
A green-walled room with a 'Champagne' sign, wicker vases with flowers, a round wooden stool, and a wooden floor.

10. Le Petit Pali St. Helena

Le Petit Pali St. Helena
4.0 star property
Upper Valley
9.6 out of 10, Exceptional, (116 reviews)
"We stayed one night and it was great!"
United States
steven
$610 nightly
The price is $703
Oct 5 - Oct 6
Total with taxes and fees
Le Petit Pali St. Helena
A two-story building with a covered porch, outdoor seating area, and a small garden.

11. Calistoga Craftsman Inn

Calistoga Craftsman Inn
3.5 star property
Calistoga
9.2 out of 10, Wonderful, (272 reviews)
"Proximity to downtown was great"
United States
Dave
$254 nightly
The price is $292
Sep 27 - Sep 28
Total with taxes and fees
Calistoga Craftsman Inn
A table with wine bottles and glasses, menus, and a view of a vineyard through large windows.

12. RustRidge Bed and Breakfast - Poolside Room

RustRidge Bed and Breakfast - Poolside Room
St Helena
9.8 out of 10, Exceptional, (12 reviews)
"The owner is very helpful and the breakfast is amazing!"
United States
James
$356 nightly
The price is $406
Sep 27 - Sep 28
Total with taxes and fees
RustRidge Bed and Breakfast - Poolside Room
A spacious living room with a large sofa, two armchairs, a coffee table, and a fireplace. There is a staircase with a metal railing on the right and a large window on the left.

13. Sonoma Stonehouse, King Room w/ Private Patio

Sonoma Stonehouse, King Room w/ Private Patio
Santa Rosa
10.0 out of 10, Exceptional, (1 review)
"What a rare gem in Sonoma County. Excellent 5 star Accommodations. We felt like royalty!"
United States
Rita W.
$467 nightly
The price is $525
Oct 23 - Oct 24
Total with taxes and fees
Sonoma Stonehouse, King Room w/ Private Patio
A narrow hallway with a wooden ceiling and a Harley-Davidson logo on the wall.

14. Easy Rider Railroad Caboose Cabin

Easy Rider Railroad Caboose Cabin
Upper Lake
$271 nightly
The price is $300
Sep 27 - Sep 28
Total with taxes and fees
Easy Rider Railroad Caboose Cabin
A view through a window with a parking area, trees, and a distant body of water.

15. Wine Country Railroad Caboose Cabin

Wine Country Railroad Caboose Cabin
Nice
$271 nightly
The price is $300
Sep 27 - Sep 28
Total with taxes and fees
Wine Country Railroad Caboose Cabin
A bathroom with a red towel hanging on the door, a white sink, and a wall-mounted light switch.

16. Casablanca Railroad Caboose Cabin

Casablanca Railroad Caboose Cabin
Upper Lake
$271 nightly
The price is $300
Sep 27 - Sep 28
Total with taxes and fees
Casablanca Railroad Caboose Cabin
A spacious living room with a fireplace, large windows, and a high ceiling.

17. Sonoma Stonehouse Hotel

Sonoma Stonehouse Hotel
Santa Rosa
$7,055 nightly
The price is $7,889
Oct 6 - Oct 7
Total with taxes and fees
Sonoma Stonehouse Hotel
A vintage train car with a bench and a small table in front, set in a park-like area with trees and a paved path.

18. London Calling Railroad Caboose Cabin

London Calling Railroad Caboose Cabin
Upper Lake
$275 nightly
The price is $304
Sep 29 - Sep 30
Total with taxes and fees
London Calling Railroad Caboose Cabin
A swimming pool with a metal ladder, surrounded by a wooden fence, and a sign indicating caution.

19. Midnight in Paris Railroad Caboose Cabin

Midnight in Paris Railroad Caboose Cabin
Upper Lake
$325 nightly
The price is $358
Sep 27 - Sep 28
Total with taxes and fees
Midnight in Paris Railroad Caboose Cabin
A poolside area with lounge chairs and a pink flamingo float.

20. Camellia Inn

Camellia Inn
3.5 star property
Healdsburg
8.6 out of 10, Excellent, (626 reviews)
"Nice place to stay for the weekend, close to town"
United States
Robb
$247 nightly
The price is $287
Oct 25 - Oct 26
Total with taxes and fees
Camellia Inn
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

Golden Haven Hot Springs

Golden Haven Hot Springs

10/10 Excellent
"Really nice people and awesome room"
Sarah 1-night trip
Posted less than an hour ago
Golden Haven Hot Springs

Find out more about Middletown

Middletown B&B information

Number of reviews
1,985
Accommodation
51 B&B
Lowest Price
$234
Highest Price
$7,889

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Middletown?
Prices for B&Bs in Middletown often vary, but you can find a great deal from $234 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Middletown B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Middletown?
The most popular time to book a B&B in Middletown is during the vibrant fall months of September and October. This period showcases the beautiful changing leaves and attracts visitors who appreciate outdoor activities like hiking and wine tasting, all set against the picturesque backdrop of the Napa Valley.

As the temperatures begin to cool, typically ranging from the mid-60s to mid-70s Fahrenheit, guests can comfortably explore the region's renowned vineyards and scenic trails. The pleasant climate makes it an ideal time for leisurely strolls through local wineries or enjoying al fresco dining with stunning views.

While the peak tourist activity occurs in September and October, offering a bustling atmosphere and numerous events, October stands out as the most budget-friendly month to visit. During this time, you can take advantage of harvest season activities without the crowds, allowing for a more intimate experience at many establishments.
What is the difference between a Middletown Bed and Breakfast and a hotel?
Every Middletown B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Middletown B&Bs.

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