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

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Check prices for these dates

Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25

Our top choices for Middletown bed & breakfast

A living room with a fireplace, leather sofas, a wooden coffee table, and a patterned rug.

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
$119 nightly
The price is $137
Aug 30 - Aug 31
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, (30 reviews)
"Beautiful location and reasonably priced for luxury accommodations."
United States
Evan
$224 nightly
The price is $250
Aug 30 - Aug 31
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, (122 reviews)
"The hosts were very hospitable, and the breakfasts were amazing!"
United States
Ann
$249 nightly
The price is $286
Aug 30 - Aug 31
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
$381 nightly
The price is $438
Aug 30 - Aug 31
Total with taxes and fees
Chateau De Vie
A green-walled room with a 'Champagne' sign, wicker vases with flowers, a round wooden stool, and a wooden floor.

5. 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
A historic building with a well-maintained facade, a prominent sign indicating 'Embrace California 128', and a flagpole with an American flag.

6. 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
Aug 30 - Aug 31
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.

7. 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
Aug 30 - Aug 31
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
9.4 out of 10, Exceptional, (59 reviews)
"Excellent stay- hidden gem"
United States
Anshuman
$299 nightly
The price is $333
Sep 28 - Sep 29
Total with taxes and fees
Bed & Barrel at Stonehouse Cellars
A table with wine bottles and glasses, menus, and a view of a vineyard through large windows.

9. 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
Aug 30 - Aug 31
Total with taxes and fees
RustRidge Bed and Breakfast - Poolside Room
An outdoor patio with a wooden deck, two wooden chairs, a table, and a large vase.

10. 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 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, (269 reviews)
"Very comfortable nice room"
United States
Chanynn
$158 nightly
The price is $181
Aug 30 - Aug 31
Total with taxes and fees
Craftsman Inn
A modern interior with a staircase, a large window with reflections, and a seating area.

12. 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
$294 nightly
The price is $341
Aug 31 - Sep 1
Total with taxes and fees
Healdsburg Inn on the Plaza, A Four Sisters Inn
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 Holiday Escape • 1BR Queen • Near Wineries

Sonoma Holiday Escape • 1BR Queen • Near Wineries
Santa Rosa
$318 nightly
The price is $354
Sep 16 - Sep 17
Total with taxes and fees
Sonoma Holiday Escape • 1BR Queen • Near Wineries

14. 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

15. 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

16. 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

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

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
A spacious living room with a fireplace, large windows, and a high ceiling.

19. Sonoma Stonehouse Hotel

Sonoma Stonehouse Hotel
Santa Rosa
$7,178 nightly
The price is $8,062
Sep 16 - Sep 17
Total with taxes and fees
Sonoma Stonehouse Hotel
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, (402 reviews)
"Great stay! Kids loved it. Very friendly staff and delicious breakfast."
United States
Carolina
$262 nightly
The price is $293
Sep 27 - Sep 28
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 La Rose

Hotel La Rose

10/10 Excellent
"Excellent service and rooms - as always!"
Karie 2-night trip
Posted 5 hours ago
Hotel La Rose

Find out more about Middletown

Middletown B&B information

Number of reviews
2,334
Accommodation
51 B&B
Lowest Price
$137
Highest Price
$8,062

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 $137 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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