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

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Check prices for these dates

Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27
In one month
Oct 9 - Oct 11
In two months
Nov 6 - Nov 8

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, (645 reviews)
"Enjoyed our stay"
United States
Pavel
$155 nightly
The price is $179
Sep 10 - Sep 11
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 10 - Sep 11
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, (123 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 10 - Sep 11
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
Sep 14 - Sep 15
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 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 14 - Sep 15
Total with taxes and fees
Embrace Calistoga
A modern interior with a staircase, a large window with reflections, and a seating area.

6. 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, (614 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
$325 nightly
The price is $378
Sep 21 - Sep 22
Total with taxes and fees
Healdsburg Inn on the Plaza, A Four Sisters Inn
An outdoor patio with a wooden deck, two wooden chairs, a table, and a large vase.

7. 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
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, (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 21 - Sep 22
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, (113 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
$560 nightly
The price is $645
Oct 5 - Oct 6
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
9.4 out of 10, Exceptional, (59 reviews)
"Excellent stay- hidden gem"
United States
Anshuman
$318 nightly
The price is $355
Oct 6 - Oct 7
Total with taxes and fees
Bed & Barrel at Stonehouse Cellars
A two-story building with a covered porch, outdoor seating area, and a small garden.

11. Craftsman Inn

Craftsman Inn
3.5 star property
Calistoga
9.2 out of 10, Wonderful, (270 reviews)
"Proximity to downtown was great"
United States
Dave
$201 nightly
The price is $231
Sep 10 - Sep 11
Total with taxes and fees
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, (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 10 - Sep 11
Total with taxes and fees
RustRidge Bed and Breakfast - Poolside Room
A bed with a red quilt, a decorative pillow, and a blanket with a UK map design.

13. London Calling Railroad Caboose Cabin

London Calling Railroad Caboose Cabin
Upper Lake
$260 nightly
The price is $288
Sep 19 - Sep 20
Total with taxes and fees
London Calling Railroad Caboose Cabin
A compact kitchen with a flat-screen TV, a coffee maker, and a window providing natural light.

14. Easy Rider Railroad Caboose Cabin

Easy Rider Railroad Caboose Cabin
Upper Lake
$287 nightly
The price is $316
Sep 10 - Sep 11
Total with taxes and fees
Easy Rider Railroad Caboose Cabin
A hallway with a wooden door leading to an outdoor area with a view of a park and a fire extinguisher mounted on the wall.

15. Wine Country Railroad Caboose Cabin

Wine Country Railroad Caboose Cabin
Nice
$287 nightly
The price is $316
Sep 10 - Sep 11
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
$280 nightly
The price is $309
Sep 13 - Sep 14
Total with taxes and fees
Casablanca Railroad Caboose Cabin
A covered porch with a flag, outdoor seating, and a stone wall.

17. Midnight in Paris Railroad Caboose Cabin

Midnight in Paris Railroad Caboose Cabin
Upper Lake
$347 nightly
The price is $380
Sep 10 - Sep 11
Total with taxes and fees
Midnight in Paris Railroad Caboose Cabin
A poolside area with lounge chairs and a pink flamingo float.

18. Camellia Inn

Camellia Inn
3.5 star property
Healdsburg
8.6 out of 10, Excellent, (625 reviews)
"Nice place to stay for the weekend, close to town"
United States
Robb
$293 nightly
The price is $340
Sep 27 - Sep 28
Total with taxes and fees
Camellia Inn
A room with a large bed, a bathtub, wooden paneling, and wall sconces.

19. Featherbed Railroad B&B Resort

Featherbed Railroad B&B Resort
3.0 star property
Nice
9.0 out of 10, Wonderful, (404 reviews)
"Great stay! Kids loved it. Very friendly staff and delicious breakfast."
United States
Carolina
$223 nightly
The price is $249
Sep 21 - Sep 22
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

UpValley Inn & Hot Springs Napa Valley, an Ascend Collection Hotel

UpValley Inn & Hot Springs Napa Valley, an Ascend Collection Hotel

8/10 Good
"The property is nice and the location perfect for the area. The room was simple, mostly clean. The bathroom inside door and the walls around it need to be scrubbed clean but the rest was nice. The pool area is simple but could use some updating around the tiles. The hot tub isn't hot but its warmer than the pool. We'd stay here again but it wouldn't be our first choice."
Unique 3-night trip
Posted 4 hours ago
UpValley Inn & Hot Springs Napa Valley, an Ascend Collection Hotel

Find out more about Middletown

Middletown B&B information

Number of reviews
2,431
Accommodation
51 B&B
Lowest Price
$179
Highest Price
$645

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 $179 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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