Middletown B&B: Find the Best Bed and Breakfast from CA $202

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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

Zhaoqi

CA $232 total

includes taxes & fees

Nov 11 - Nov 12

A patio with outdoor furniture, a stone table, and a view of vineyards and mountains.

2. Chateau De Vie

Calistoga

Bruce

CA $573 total

includes taxes & fees

Dec 7 - Dec 8

A white teepee tent set up in a natural landscape with trees and a mountain in the background.

3. Glamping at Bliss Mountain Tepee with a Trailer. Hiking on our 40 magical acres

Lower Lake

CA $305 total

includes taxes & fees

Dec 7 - Dec 8

A house with a porch, potted plants, and a brick wall.

4. Bear Flag Inn

Calistoga

Jacob

CA $400 total

includes taxes & fees

Dec 7 - Dec 8

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

Calistoga

Melanie

CA $466 total

includes taxes & fees

Nov 22 - Nov 23

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

Daniel M

CA $351 total

includes taxes & fees

Nov 19 - Nov 20

A landscaped garden with a pathway leading to a building with a green roof and stone columns.

7. Thorn Hill Vineyard Villas

Lower Lake

Evan

CA $315 total

includes taxes & fees

Nov 10 - Nov 11

A green-walled room with a 'Champagne' sign, wicker vases with flowers, a round wooden stool, and a wooden floor.

8. Le Petit Pali St. Helena

Upper Valley

William

CA $525 total

includes taxes & fees

Dec 1 - Dec 2

A house with a covered patio, outdoor seating, and a garden.

9. Grape Leaf Inn

Healdsburg

Eric

CA $439 total

includes taxes & fees

Nov 16 - Nov 17

A garden pathway leading to a white building with a traditional design, surrounded by neatly trimmed hedges and a white picket fence.

10. Inn St Helena

Downtown St. Helena

Ron

CA $469 total

includes taxes & fees

Nov 11 - Nov 12

A two-story building with a covered porch, outdoor seating area, and a small garden.

11. Calistoga Craftsman Inn

Calistoga

Dave

CA $259 total

includes taxes & fees

Nov 8 - Nov 9

A house with a stone exterior, a red-tiled roof, and a driveway leading to a gated entrance.

12. Bed & Breakfast Hot Tub & Views for Explorers

Healdsburg

CA $437 total

includes taxes & fees

Nov 8 - Nov 9

A stone cabin with a pond in front, illuminated by string lights.

13. Bed & Barrel at Stonehouse Cellars

Clearlake Oaks

Anshuman

CA $458 total

includes taxes & fees

Dec 6 - Dec 7

14. Asti Room: Largest Suite w/ Exclusive Winery Perks

Healdsburg

CA $650 total

includes taxes & fees

Dec 7 - Dec 8

A two-story house with a stone facade, a red roof, and a landscaped driveway.

15. Wine Country B&B Retreat Near Downtown Healdsburg

Healdsburg

CA $646 total

includes taxes & fees

Nov 9 - Nov 10

A swimming pool with lounge chairs and a bicycle.

16. RustRidge Bed and Breakfast - Poolside Room

St Helena

James

CA $571 total

includes taxes & fees

Dec 7 - Dec 8

A hotel room with a bed, a vanity with a mirror, a red armchair, and a small table with a glass and bottles.

17. Casablanca Railroad Caboose Cabin

Upper Lake

CA $410 total

includes taxes & fees

Nov 8 - Nov 9

A room with a wooden ceiling, a black leather chair, a bathtub, and a dining area with a TV.

18. Easy Rider Railroad Caboose Cabin

Upper Lake

CA $421 total

includes taxes & fees

Dec 7 - Dec 8

A nighttime outdoor area with a wooden deck, a red building, and a view of the hills.

19. Wine Country Railroad Caboose Cabin

Nice

CA $421 total

includes taxes & fees

Dec 7 - Dec 8

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.

20. London Calling Railroad Caboose Cabin

Upper Lake

CA $476 total

includes taxes & fees

Dec 7 - Dec 8

View all properties

Learn more about Middletown

Soak in mineral-rich waters at Harbin Hot Springs, where hiking trails lead to peaceful meditation areas. Wine lovers can sample local vintages at family-owned tasting rooms along Middletown's charming main street.

See all hotels in Middletown

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

Top reviews in Middletown

Embrace Calistoga

Calistoga

10/10 Excellent

Our stay at the Luxe was very enjoyable. The owners (Chris & Brent) are outstanding hosts and go above and beyond to make your stay as comfortable as possible. The daily happy hours from 5-7 are great -- the selected wines are very good as are the charcuterie boards prepared for each guest. The breakfast (which is included in the rate) is very gourmet. We had 4 courses each morning and all were delicious. I am a very big foodie, so quite enjoyed the high quality and very tasty dishes...

natasha

Calistoga Wine Way Inn

Calistoga

10/10 Excellent

James

Bear Flag Inn

Calistoga

10/10 Excellent

Sheri Lynn

Healdsburg Inn on the Plaza, A Four Sisters Inn

Healdsburg

10/10 Excellent

Onofrio

Grape Leaf Inn

Healdsburg

10/10 Excellent

We received a very warm welcome and wine tasting just after our arrival. The breakfasts were excellent- varied, a good size and delicious. The staff were very helpful and accommodating. The inn is lovely, well located within easy walking distance of the central square, shopping and restaurants in Healdsburg and in a quiet area. The bathroom in our room was a little small but certainly adequate. Overall, a wonderful choice.

Anonymous traveller

A historic building with a prominent arched entrance, a sign reading "Cambria Inn," and a well-maintained garden with red flowers and pathway lighting.

Camellia Inn

Healdsburg

10/10 Excellent

JB

A grassy area with trees and a red train car labeled 'Santa Fe' in the background.

Featherbed Railroad B&B Resort

Nice

10/10 Excellent

Wade

Frequently Asked Questions

Searching for B&Bs in Middletown?

If you want to find a place to stay with fewer rooms than a hotel and an intimate environment, a B&B may be the perfect thing for your vacation to Middletown. If your ideal vacation to Middletown includes spending lots of time outside, Boggs Mountain Demonstration State Forest is a good spot to enjoy the scenery.

Why should you consider B&Bs instead of traditional hotels?

B&Bs all have a unique charm. Whether it’s a garden for guests to admire or a sunlit breakfast nook to enjoy your morning cup of coffee, the little details are what make bed and breakfasts a home away from home.

What are the best B&Bs in Middletown?

Below are some well-liked B&Bs in the area: Le Petit Pali St. Helena: 16.9 mi (27.2 km) from the heart of Middletown. Enjoy the designer toiletries and patio area. Calistoga Wine Way Inn: 8 rooms. 12.4 mi (20 km) from the downtown core. Enjoy the designer toiletries and library. Camellia Inn: 9 rooms. Situated 16.7 mi (26.9 km) from the heart of Middletown. Enjoy the free full breakfast and spa. Healdsburg Inn on the Plaza, A Four Sisters Inn: 12 rooms. 16.9 mi (27.2 km) from the heart of downtown. Enjoy the massage services and fireplace in the lobby. Chateau De Vie: 5 rooms. Located 11 mi (17.6 km) from the core of Middletown. Enjoy the local cuisine breakfast and private yard.

What's the best time of year to book my B&B in Middletown?

When you're dreaming of a trip to Middletown, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are December and January with an average of 48°F. Average annual precipitation for Middletown is 26 inches.

What is there to do in Middletown?

If you're looking for some activities to entertain you on your trip, consider visiting Beaver Creek Vineyards and Langtry Estate and Vineyards. You might put Twin Pine Casino and Rabbit Hill Preserve on your list if you want to see more of the area.

How can I get to and around Middletown?

You can map out your trip in and around Middletown ahead of time with these transportation options. Fly into Santa Rosa, CA (STS-Sonoma County), which is located 19.6 mi (31.6 km) from the heart of the city. If you'd like to explore around the area, you may want a rental car for your journey.

Find a Bed and Breakfast in Middletown from CA $202

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middletown bed & breakfast

1. Calistoga Wine Way Inn

2. Chateau De Vie

3. Glamping at Bliss Mountain Tepee with a Trailer. Hiking on our 40 magical acres

4. Bear Flag Inn

5. Embrace Calistoga

6. Healdsburg Inn on the Plaza, A Four Sisters Inn

7. Thorn Hill Vineyard Villas

8. Le Petit Pali St. Helena

9. Grape Leaf Inn

10. Inn St Helena

11. Calistoga Craftsman Inn

12. Bed & Breakfast Hot Tub & Views for Explorers

13. Bed & Barrel at Stonehouse Cellars

14. Asti Room: Largest Suite w/ Exclusive Winery Perks

15. Wine Country B&B Retreat Near Downtown Healdsburg

16. RustRidge Bed and Breakfast - Poolside Room

17. Casablanca Railroad Caboose Cabin

18. Easy Rider Railroad Caboose Cabin

19. Wine Country Railroad Caboose Cabin

20. London Calling Railroad Caboose Cabin

Learn more about Middletown

Top reviews in Middletown

Embrace Calistoga

10/10 Excellent

Frequently Asked Questions

Searching for B&Bs in Middletown?

Why should you consider B&Bs instead of traditional hotels?

What are the best B&Bs in Middletown?

What's the best time of year to book my B&B in Middletown?

What is there to do in Middletown?

How can I get to and around Middletown?

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