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Book Middletown Bed & Breakfast

Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

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, (649 reviews)
"A very good place to stay. The house is so clean, and the host is so friendly and helpful."
United States
Zhaoqi
$177 nightly
The price is $203
Nov 1 - Nov 2
Total with taxes and fees
Calistoga Wine Way Inn
A house with a porch, potted plants, and a brick wall.

2. Bear Flag Inn

Bear Flag Inn
3.0 star property
Calistoga
9.4 out of 10, Exceptional, (126 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
Oct 18 - Oct 19
Total with taxes and fees
Bear Flag Inn
A landscaped garden with a pathway leading to a building with a green roof and stone columns.

3. Thorn Hill Vineyard Villas

Thorn Hill Vineyard Villas
3.5 star property
Lower Lake
8.8 out of 10, Excellent, (32 reviews)
"Beautiful location and reasonably priced for luxury accommodations."
United States
Evan
$224 nightly
The price is $250
Oct 21 - Oct 22
Total with taxes and fees
Thorn Hill Vineyard Villas
A modern interior with a staircase, a large window with reflections, and a seating area.

4. 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, (620 reviews)
"Fantastic location, beautiful hotel"
United States
Daniel M
$328 nightly
The price is $381
Nov 4 - Nov 5
Total with taxes and fees
Healdsburg Inn on the Plaza, A Four Sisters Inn
A patio with outdoor furniture, a stone table, and a view of vineyards and mountains.

5. 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 18 - Oct 19
Total with taxes and fees
Chateau De Vie
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, (179 reviews)
"What a great location, beautiful clean, great breakfast great coffee and coffee options. Staff was super helpful. Would definitely come back here if I was in Healdsburg."
United States
Eric
$287 nightly
The price is $333
Nov 1 - Nov 2
Total with taxes and fees
Grape Leaf Inn
A wooden chest of drawers with metal accents, a lamp, and a framed artwork on a wall.

7. 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
Oct 19 - Oct 20
Total with taxes and fees
Embrace Calistoga
A garden pathway leading to a white building with a traditional design, surrounded by neatly trimmed hedges and a white picket fence.

8. Inn St Helena

Inn St Helena
3.0 star property
Downtown St. Helena
9.6 out of 10, Exceptional, (165 reviews)
"The property was perfect and located walking distance to downtown. We will be back."
United States
Danny
$291 nightly
The price is $335
Oct 19 - Oct 20
Total with taxes and fees
Inn St Helena
A green-walled room with a 'Champagne' sign, wicker vases with flowers, a round wooden stool, and a wooden floor.

9. Le Petit Pali St. Helena

Le Petit Pali St. Helena
4.0 star property
Upper Valley
9.6 out of 10, Exceptional, (122 reviews)
"Beautiful property and friendly and helpful staff."
United States
William
$465 nightly
The price is $536
Nov 10 - Nov 11
Total with taxes and fees
Le Petit Pali St. Helena
A stone cabin with a pond in front, illuminated by string lights.

10. Bed & Barrel at Stonehouse Cellars

Bed & Barrel at Stonehouse Cellars
4.0 star property
Clearlake Oaks
9.2 out of 10, Wonderful, (62 reviews)
"Excellent stay- hidden gem"
United States
Anshuman
$299 nightly
The price is $333
Nov 15 - Nov 16
Total with taxes and fees
Bed & Barrel at Stonehouse Cellars
A poolside area with lounge chairs and a pink flamingo float.

11. Camellia Inn

Camellia Inn
3.5 star property
Healdsburg
8.6 out of 10, Excellent, (632 reviews)
"The family suite worked fine for 4 adults. The breakfast and afternoon wine and cookies were a great touch. Easy to park and check in. Loved our stay!"
United States
Erika
$117 nightly
The price is $136
Nov 9 - Nov 10
Total with taxes and fees
Camellia 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
$377 nightly
The price is $427
Oct 18 - Oct 19
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, (2 reviews)
"Perfect location to get to our winery wedding destination."
United States
B B.
$405 nightly
The price is $452
Oct 23 - Oct 24
Total with taxes and fees
Sonoma Stonehouse, King Room w/ Private Patio
A view through a window with a parking area, trees, and a distant body of water.

14. Wine Country Railroad Caboose Cabin

Wine Country Railroad Caboose Cabin
Nice
$287 nightly
The price is $316
Oct 18 - Oct 19
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.

15. Casablanca Railroad Caboose Cabin

Casablanca Railroad Caboose Cabin
Upper Lake
$280 nightly
The price is $309
Oct 18 - Oct 19
Total with taxes and fees
Casablanca Railroad Caboose Cabin
A narrow hallway with a wooden ceiling and a Harley-Davidson logo on the wall.

16. Easy Rider Railroad Caboose Cabin

Easy Rider Railroad Caboose Cabin
Upper Lake
$287 nightly
The price is $316
Oct 18 - Oct 19
Total with taxes and fees
Easy Rider Railroad Caboose Cabin
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.

17. London Calling Railroad Caboose Cabin

London Calling Railroad Caboose Cabin
Upper Lake
$288 nightly
The price is $317
Oct 18 - Oct 19
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.

18. Midnight in Paris Railroad Caboose Cabin

Midnight in Paris Railroad Caboose Cabin
Upper Lake
$347 nightly
The price is $380
Oct 18 - Oct 19
Total with taxes and fees
Midnight in Paris Railroad Caboose Cabin
A two-story building with a covered porch, outdoor seating area, and a small garden.

19. 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
$231 nightly
The price is $265
Nov 4 - Nov 5
Total with taxes and fees
Calistoga Craftsman Inn
A room with a large bed, a bathtub, wooden paneling, and wall sconces.

20. Featherbed Railroad B&B Resort

Featherbed Railroad B&B Resort
3.0 star property
Nice
9.0 out of 10, Wonderful, (408 reviews)
"Great stay! Kids loved it. Very friendly staff and delicious breakfast."
United States
Carolina
$217 nightly
The price is $242
Oct 25 - Oct 26
Total with taxes and fees
Featherbed Railroad B&B Resort
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 Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

10/10 Excellent
"The manager, Evan was wonderful. Super helpful, kind and patient ! I will be returning around hliday time. Thank you"
Lisa 1-night trip
Posted 7 hours ago
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

Find out more about Middletown

Middletown B&B information

Number of reviews
2,324
Accommodation
51 B&B
Lowest Price
$136
Highest Price
$536

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 $136 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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