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Check prices for these dates

Next weekend
Aug 7 - Aug 9
In two weeks
Aug 14 - Aug 16
In one month
Aug 28 - Aug 30
In two months
Sep 25 - Sep 27

Our top choices for Middletown bed & breakfast

House, Multiple Bedrooms | Dining room

1. Calistoga Wine Way Inn

Calistoga Wine Way Inn
3.0 star property
Calistoga
8.8 out of 10, Excellent, (633 reviews)
"It was very easy to find and within walking distance of all the shops and restaurants. It was a very nice place with ample outside sitting space. There is no staff on site that we seen, the check in and check out was very simple and no stress. "
United States
Daniel
$126 nightly
The price is $145
Aug 4 - Aug 5
Total with taxes and fees
Calistoga Wine Way Inn
Interior entrance

2. Le Petit Pali St. Helena

Le Petit Pali St. Helena
4.0 star property
Upper Valley
9.6 out of 10, Exceptional, (101 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
$470 nightly
The price is $541
Aug 5 - Aug 6
Total with taxes and fees
Le Petit Pali St. Helena
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
$252 nightly
The price is $281
Aug 3 - Aug 4
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
$406 nightly
The price is $467
Aug 9 - Aug 10
Total with taxes and fees
Chateau De Vie
Property entrance

5. Bear Flag Inn

Bear Flag Inn
3.0 star property
Calistoga
9.4 out of 10, Exceptional, (121 reviews)
"The hosts were very hospitable, and the breakfasts were amazing!"
United States
Ann
$249 nightly
The price is $286
Aug 3 - Aug 4
Total with taxes and fees
Bear Flag Inn
Palisade Cottage | Premium bedding, desk, iron/ironing board, WiFi (free)

6. Potter's Foothill House

Potter's Foothill House
3.5 star property
Calistoga
10.0 out of 10, Exceptional, (27 reviews)
"The only issue we had was the way we drove in from the 101 coming from north it was very difficult. Don’t come in that way. Other than that, the place is beautiful and the people are very helpful and sweet."
United States
Darylle
$380 nightly
The price is $436
Aug 12 - Aug 13
Total with taxes and fees
Potter's Foothill House
Front of property - evening/night

7. Embrace Calistoga

Embrace Calistoga
3.5 star property
Calistoga
10.0 out of 10, Exceptional, (55 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
Aug 3 - Aug 4
Total with taxes and fees
Embrace Calistoga
Front of property

8. 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, (607 reviews)
"All around great place to stay"
United States
Shelly
$257 nightly
The price is $299
Aug 3 - Aug 4
Total with taxes and fees
Healdsburg Inn on the Plaza, A Four Sisters Inn
Exterior

9. 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
$299 nightly
The price is $333
Aug 31 - Sep 1
Total with taxes and fees
Bed & Barrel at Stonehouse Cellars
Front of property

10. Inn St Helena

Inn St Helena
3.0 star property
Downtown St. Helena
9.6 out of 10, Exceptional, (162 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
$276 nightly
The price is $317
Aug 4 - Aug 5
Total with taxes and fees
Inn St Helena
House, 5 Bedrooms | Terrace/patio

11. Craftsman Inn

Craftsman Inn
3.5 star property
Calistoga
9.2 out of 10, Wonderful, (267 reviews)
"Clean beautiful spot "
United States
Lizbet
$183 nightly
The price is $210
Aug 3 - Aug 4
Total with taxes and fees
Craftsman Inn
Suite | Balcony

12. Grape Leaf Inn

Grape Leaf Inn
4.0 star property
Healdsburg
9.4 out of 10, Exceptional, (174 reviews)
"Just a beautiful property a home away from home!! Highly recommend!!"
United States
Anthony
$213 nightly
The price is $248
Aug 3 - Aug 4
Total with taxes and fees
Grape Leaf Inn
Interior

13. 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
$374 nightly
The price is $424
Aug 3 - Aug 4
Total with taxes and fees
RustRidge Bed and Breakfast - Poolside Room
Miscellaneous

14. Easy Rider Railroad Caboose Cabin

Easy Rider Railroad Caboose Cabin
Upper Lake
$1,252 nightly
The price is $1,285
Aug 3 - Aug 4
Total with taxes and fees
Easy Rider Railroad Caboose Cabin
Point of interest

15. Wine Country Railroad Caboose Cabin

Wine Country Railroad Caboose Cabin
Nice
$1,326 nightly
The price is $1,359
Aug 3 - Aug 4
Total with taxes and fees
Wine Country Railroad Caboose Cabin
WiFi, bed sheets

16. Midnight in Paris Railroad Caboose Cabin

Midnight in Paris Railroad Caboose Cabin
Upper Lake
$1,275 nightly
The price is $1,308
Aug 3 - Aug 4
Total with taxes and fees
Midnight in Paris Railroad Caboose Cabin
Exterior

17. Casablanca Railroad Caboose Cabin

Casablanca Railroad Caboose Cabin
Upper Lake
$1,252 nightly
The price is $1,285
Aug 3 - Aug 4
Total with taxes and fees
Casablanca Railroad Caboose Cabin
Property grounds

18. London Calling Railroad Caboose Cabin

London Calling Railroad Caboose Cabin
Upper Lake
$1,220 nightly
The price is $1,249
Aug 3 - Aug 4
Total with taxes and fees
London Calling Railroad Caboose Cabin
Seasonal outdoor pool, open 8:30 AM to 9:00 PM, sun loungers

19. Camellia Inn

Camellia Inn
3.5 star property
Healdsburg
8.6 out of 10, Excellent, (620 reviews)
"Cosy room and nice options on the property to sit and have a quiet glass of wine."
United States
Alodie
$311 nightly
The price is $360
Aug 3 - Aug 4
Total with taxes and fees
Camellia Inn
Signature Cabin, Private Bathroom (Mystery on the Orient Express) | 1 bedroom, hypo-allergenic bedding available

20. Featherbed Railroad B&B Resort

Featherbed Railroad B&B Resort
3.0 star property
Nice
9.0 out of 10, Wonderful, (400 reviews)
"Great stay! Kids loved it. Very friendly staff and delicious breakfast."
United States
Carolina
$299 nightly
The price is $333
Aug 4 - Aug 5
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

Hotel E

Hotel E

8/10 Good
"Overall great experience"
albert 2-night trip
Posted 2 hours ago
Hotel E

Find out more about Middletown

Middletown B&B information

Number of reviews
2,949
Accommodation
40 B&B
Lowest Price
$145
Highest Price
$1,359

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 $145 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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