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

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    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Middletown bed & breakfast

Whole House, 8 Rooms w/Private baths | Living area

1. Calistoga Wine Way Inn

Calistoga Wine Way Inn
3.0 star property
Calistoga
8.8 out of 10, Excellent, (645 reviews)
"Enjoyed our stay"
United States
Pavel
$130 nightly
The price is $150
Sep 7 - Sep 8
Total with taxes and fees
Calistoga Wine Way Inn
Property entrance

2. Bear Flag Inn

Bear Flag Inn
3.0 star property
Calistoga
9.4 out of 10, Exceptional, (122 reviews)
"The hosts were very hospitable, and the breakfasts were amazing!"
United States
Ann
$249 nightly
The price is $286
Sep 1 - Sep 2
Total with taxes and fees
Bear Flag Inn
Exterior

3. Thorn Hill Vineyard Villas

Thorn Hill Vineyard Villas
3.5 star property
Lower Lake
8.8 out of 10, Excellent, (30 reviews)
"Beautiful location and reasonably priced for luxury accommodations."
United States
Evan
$224 nightly
The price is $250
Sep 6 - Sep 7
Total with taxes and fees
Thorn Hill Vineyard Villas
Exterior

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
$433 nightly
The price is $498
Sep 16 - Sep 17
Total with taxes and fees
Chateau De Vie
Front of property - evening/night

5. Embrace Calistoga

Embrace Calistoga
3.5 star property
Calistoga
10.0 out of 10, Exceptional, (56 reviews)
"Chris and Brent were amazing hosts. The menu and libations for weekend breakfasts and wine/cheese hours were delicious and on par with a fine dining restaurant. Beautiful room, bed and bath were very comfortable."
United States
Marc
$329 nightly
The price is $378
Sep 1 - Sep 2
Total with taxes and fees
Embrace Calistoga
Interior entrance

6. Le Petit Pali St. Helena

Le Petit Pali St. Helena
4.0 star property
Upper Valley
9.6 out of 10, Exceptional, (109 reviews)
"Very convenient location, our room was spacious, hot tub was a nice surprise, delicious breakfast, and beautiful view from the room"
United States
ferda
$500 nightly
The price is $576
Sep 8 - Sep 9
Total with taxes and fees
Le Petit Pali St. Helena
Front of property

7. 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, (613 reviews)
"It was nice to be on the plaza to walk everywhere. The staff were very friendly and helpful. The wine in the afternoon and breakfast in the morning were both plentiful."
United States
Valerie
$301 nightly
The price is $350
Sep 1 - Sep 2
Total with taxes and fees
Healdsburg Inn on the Plaza, A Four Sisters Inn
Front of property

8. Inn St Helena

Inn St Helena
3.0 star property
Downtown St. Helena
9.6 out of 10, Exceptional, (163 reviews)
"Great little Inn with exceptional service and an ideal location. The breakfast was amazing! We only stayed one night but would have gladly stayed many."
United States
Kelly
$291 nightly
The price is $335
Sep 3 - Sep 4
Total with taxes and fees
Inn St Helena
Suite | Balcony

9. Grape Leaf Inn

Grape Leaf Inn
4.0 star property
Healdsburg
9.4 out of 10, Exceptional, (175 reviews)
"Just a beautiful property a home away from home!! Highly recommend!!"
United States
Anthony
$301 nightly
The price is $349
Sep 27 - Sep 28
Total with taxes and fees
Grape Leaf Inn
Exterior

10. Bed & Barrel at Stonehouse Cellars

Bed & Barrel at Stonehouse Cellars
4.0 star property
Clearlake Oaks
9.4 out of 10, Exceptional, (59 reviews)
"Excellent stay- hidden gem"
United States
Anshuman
$290 nightly
The price is $324
Oct 1 - Oct 2
Total with taxes and fees
Bed & Barrel at Stonehouse Cellars
House, 5 Bedrooms | Terrace/patio

11. Craftsman Inn

Craftsman Inn
3.5 star property
Calistoga
9.2 out of 10, Wonderful, (269 reviews)
"Very comfortable nice room"
United States
Chanynn
$171 nightly
The price is $197
Sep 2 - Sep 3
Total with taxes and fees
Craftsman Inn
Interior

12. RustRidge Bed and Breakfast - Poolside Room

RustRidge Bed and Breakfast - Poolside Room
St Helena
9.8 out of 10, Exceptional, (11 reviews)
"Susan and Jim were wonderful! We arrived early and she was so welcoming. Their dogs greeted us like we were family. Max and Cowboy. The views were breathtaking. And, it was so quiet. The breakfast was delicious, you would not go hungry. The pool was wonderful and the hottub for an evening s"
United States
Carol
$377 nightly
The price is $427
Sep 1 - Sep 2
Total with taxes and fees
RustRidge Bed and Breakfast - Poolside Room
Exterior

13. London Calling Railroad Caboose Cabin

London Calling Railroad Caboose Cabin
Upper Lake
$275 nightly
The price is $303
Sep 19 - Sep 20
Total with taxes and fees
London Calling Railroad Caboose Cabin
Room

14. Easy Rider Railroad Caboose Cabin

Easy Rider Railroad Caboose Cabin
Upper Lake
$287 nightly
The price is $316
Sep 9 - Sep 10
Total with taxes and fees
Easy Rider Railroad Caboose Cabin
Interior

15. Wine Country Railroad Caboose Cabin

Wine Country Railroad Caboose Cabin
Nice
$287 nightly
The price is $316
Sep 9 - Sep 10
Total with taxes and fees
Wine Country Railroad Caboose Cabin
Interior

16. Sonoma Stonehouse Hotel

Sonoma Stonehouse Hotel
Santa Rosa
$7,135 nightly
The price is $8,019
Sep 24 - Sep 25
Total with taxes and fees
Sonoma Stonehouse Hotel
Room

17. Casablanca Railroad Caboose Cabin

Casablanca Railroad Caboose Cabin
Upper Lake
$280 nightly
The price is $309
Sep 13 - Sep 14
Total with taxes and fees
Casablanca Railroad Caboose Cabin
Room

18. Midnight in Paris Railroad Caboose Cabin

Midnight in Paris Railroad Caboose Cabin
Upper Lake
$347 nightly
The price is $380
Sep 9 - Sep 10
Total with taxes and fees
Midnight in Paris Railroad Caboose Cabin
Pool

19. Camellia Inn

Camellia Inn
3.5 star property
Healdsburg
8.6 out of 10, Excellent, (623 reviews)
"Nice place to stay for the weekend, close to town"
United States
Robb
$362 nightly
The price is $420
Sep 1 - Sep 2
Total with taxes and fees
Camellia Inn
Signature Cabin, Private Bathroom (Mystery on the Orient Express)

20. Featherbed Railroad B&B Resort

Featherbed Railroad B&B Resort
3.0 star property
Nice
9.0 out of 10, Wonderful, (402 reviews)
"Great stay! Kids loved it. Very friendly staff and delicious breakfast."
United States
Carolina
$254 nightly
The price is $284
Sep 28 - Sep 29
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

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

10/10 Excellent
"Nice hotel with comfortable room within walking distance to downtown Healdsburg."
PELLIE 1-night trip
Posted 1 hour ago
Dry Creek Inn MOD Collection by Sonesta

Find out more about Middletown

Middletown B&B information

Number of reviews
2,957
Accommodation
51 B&B
Lowest Price
$150
Highest Price
$8,019

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 $150 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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