A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Windsor bed & breakfast

A poolside area with lounge chairs and a pink flamingo float.

1. Camellia Inn

Camellia Inn
3.5 star property
Healdsburg
9.0 out of 10, Wonderful, (641 reviews)
"Great stay. Comfy room, good service, ideal location, and nice breakfast. I would definitely stay here again."
United States
Chris
$196 nightly
The price is $227
Dec 1 - Dec 2
Total with taxes and fees
Camellia Inn
A view of the Healdsburg Inn on the Plaza, featuring a modern interior with a staircase, seating area, and decorative lighting.

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

Healdsburg Inn on the Plaza, A Four Sisters Inn
3.5 star property
Healdsburg
9.0 out of 10, Wonderful, (624 reviews)
"Fantastic location, beautiful hotel"
United States
Daniel M
$231 nightly
The price is $268
Nov 22 - Nov 23
Total with taxes and fees
Healdsburg Inn on the Plaza, A Four Sisters Inn
A wooden deck with a view of a river and forest. There is a table with a vase of sunflowers and an American flag.

3. Highland Dell Lodge

Highland Dell Lodge
3.0 star property
Monte Rio
9.2 out of 10, Wonderful, (675 reviews)
"Definitely will stay there again!"
United States
Nancy
$112 nightly
The price is $127
Nov 15 - Nov 16
Total with taxes and fees
Highland Dell Lodge
A house with a covered patio, outdoor seating, and a garden.

4. Grape Leaf Inn

Grape Leaf Inn
4.0 star property
Healdsburg
9.4 out of 10, Exceptional, (181 reviews)
"What a great location, beautiful clean, great breakfast great coffee and coffee options. Staff was super helpful. Would definitely come back here if I was in Healdsburg."
United States
Eric
$201 nightly
The price is $234
Nov 16 - Nov 17
Total with taxes and fees
Grape Leaf Inn
A large house with a circular driveway, surrounded by trees and a view of a distant town.

5. Bed & Breakfast Hot Tub & Views for Explorers

Bed & Breakfast Hot Tub & Views for Explorers
Healdsburg
$257 nightly
The price is $295
Nov 16 - Nov 17
Total with taxes and fees
Bed & Breakfast Hot Tub & Views for Explorers
A large house with a circular driveway, surrounded by trees and a view of a distant town.

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

Asti Room: Largest Suite w/ Exclusive Winery Perks
Healdsburg
$404 nightly
The price is $465
Nov 16 - Nov 17
Total with taxes and fees
Asti Room: Largest Suite w/ Exclusive Winery Perks
A two-story house with a stone facade, a red roof, and a landscaped driveway.

7. Wine Country B&B Retreat Near Downtown Healdsburg

Wine Country B&B Retreat Near Downtown Healdsburg
Healdsburg
$403 nightly
The price is $462
Nov 16 - Nov 17
Total with taxes and fees
Wine Country B&B Retreat Near Downtown Healdsburg
A coastal landscape with a grassy path leading to the sea, featuring rocky outcrops and a clear view of the ocean.

8. Inn at Occidental

Inn at Occidental
3.5 star property
Occidental
9.4 out of 10, Exceptional, (524 reviews)
"Friendly staff. Wonderful breakfasts. Wine tastings with local vintners. Overall, an excellent stay."
United States
Stacie
$224 nightly
The price is $255
Nov 15 - Nov 16
Total with taxes and fees
Inn at Occidental
A house with a porch, potted plants, and a brick wall.

9. Bear Flag Inn

Bear Flag Inn
3.0 star property
Calistoga
9.6 out of 10, Exceptional, (127 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
Nov 15 - Nov 16
Total with taxes and fees
Bear Flag Inn
A deck with four striped chairs and a square table, surrounded by large trees and a sandy area.

10. The Gables Wine Country Inn

The Gables Wine Country Inn
5.0 star property
Santa Rosa
10.0 out of 10, Exceptional, (38 reviews)
"The breakfast was outstanding!"
United States
Gloria
$296 nightly
The price is $337
Dec 2 - Dec 3
Total with taxes and fees
The Gables Wine Country Inn
A two-story building with a covered porch, a sign indicating a vacancy, and a sign for the Wine Way Inn.

11. Calistoga Wine Way Inn

Calistoga Wine Way Inn
3.0 star property
Calistoga
9.0 out of 10, Wonderful, (651 reviews)
"Such a cute inn in a great location right by downtown! Parking was easy, and check-in and check-out communication was simple and hassle-free. The room was clean and comfortable. Would definitely stay here again!"
United States
Wendy
$131 nightly
The price is $151
Nov 23 - Nov 24
Total with taxes and fees
Calistoga Wine Way Inn
A green-walled room with a 'Champagne' sign, wicker vases with flowers, a round wooden stool, and a wooden floor.

12. Le Petit Pali St. Helena, a Member of Design Hotels

Le Petit Pali St. Helena, a Member of Design Hotels
4.0 star property
Upper Valley
9.6 out of 10, Exceptional, (126 reviews)
"Beautiful property and friendly and helpful staff."
United States
William
$310 nightly
The price is $357
Dec 15 - Dec 16
Total with taxes and fees
Le Petit Pali St. Helena, a Member of Design Hotels
A patio with outdoor furniture, a stone table, and a view of vineyards and mountains.

13. Chateau De Vie

Chateau De Vie
3.0 star property
Calistoga
9.8 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay."
United States
Bruce
$383 nightly
The price is $440
Nov 30 - Dec 1
Total with taxes and fees
Chateau De Vie
A garden pathway leading to a white building with a traditional design, surrounded by neatly trimmed hedges and a white picket fence.

14. Inn St Helena

Inn St Helena
3.0 star property
Downtown St. Helena
9.6 out of 10, Exceptional, (165 reviews)
"They were very accommodating and we enjoyed the breakfast."
United States
Ron
$291 nightly
The price is $335
Nov 19 - Nov 20
Total with taxes and fees
Inn St Helena
A historic building with a sign reading "Embrace Calistoga No-Vacation."

15. Embrace Calistoga

Embrace Calistoga
3.5 star property
Calistoga
10.0 out of 10, Exceptional, (58 reviews)
"Very comfortable! The owners are wonderful and we had an amazing breakfast!"
United States
Elizabeth
$289 nightly
The price is $332
Nov 22 - Nov 23
Total with taxes and fees
Embrace Calistoga
A garden pathway leading to a building with a porch covered in climbing plants.

16. Beltane Ranch

Beltane Ranch
4.0 star property
Glen Ellen
9.8 out of 10, Exceptional, (118 reviews)
"What a lovely place. We cannot wait to go back to this ranch. The staff was kind and sweet and so accommodating. The breakfast was farm fresh every day and it was so delicious some of the best breakfasts I’ve had. The rooms were dreamy and gorgeous. The beds were so comfortable. There was eight of us and we all had the best sleep there. I cannot recommend a better place."
United States
Bobbi
$348 nightly
The price is $397
Nov 15 - Nov 16
Total with taxes and fees
Beltane Ranch
Front of property

17. Mine + Farm, The Inn at Guerneville, CA

Mine + Farm, The Inn at Guerneville, CA
3.5 star property
Guerneville
9.4 out of 10, Exceptional, (153 reviews)
"Beautiful property, great location, delicious breakfast. "
United States
Amy
$335 nightly
The price is $382
Nov 15 - Nov 16
Total with taxes and fees
Mine + Farm, The Inn at Guerneville, CA
A two-story building with a covered porch, outdoor seating area, and a small garden.

18. Calistoga Craftsman Inn

Calistoga Craftsman Inn
3.5 star property
Calistoga
9.4 out of 10, Exceptional, (275 reviews)
"Proximity to downtown was great"
United States
Dave
$189 nightly
The price is $217
Nov 16 - Nov 17
Total with taxes and fees
Calistoga Craftsman Inn
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 Windsor Hotel Reviews

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

8/10 Good
"The best aspect of Dry Creek Inn is its location. Right of Hwy 101 and only about 5 minutes from downtown Healdsburg. Although close to the street, it really was fairly quiet. Easy access in and out. Rooms were cleaned and serviced daily, Rooms are not updated, but I found them clean and roomy. Great coffee shop (Plank Coffee) and grocery market (Big Johns) just a short walk away. Compared to other hotels nearby, charging 300+ per night, it is a real bargain. I would definitely stay here again."
Daniel 4-night trip
Posted 12 hours ago
Dry Creek Inn MOD Collection by Sonesta

Find out more about Windsor

Windsor B&B information

Number of reviews
3,521
Accommodation
49 B&B
Lowest Price
$127
Highest Price
$440

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Windsor?
Prices for B&Bs in Windsor often vary, but you can find a great deal from $127 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windsor 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 Bed & Breakfast in Windsor?
The best time to book a B&B in Windsor is during the peak season from May to September, when the town truly comes alive with vibrant energy. This period is superb for travelers seeking outdoor experiences, as the weather is warm, with temperatures ranging from the mid-60s to the low 80s Fahrenheit. Visitors can enjoy leisurely strolls along the beautiful waterfront, explore local parks, or indulge in wine tasting tours at nearby vineyards, making it an ideal backdrop for both relaxation and adventure.

Among these months, June stands out as particularly popular, drawing in tourists eager to partake in various local festivals and events. The lively atmosphere enhances the charm of Windsor, with bustling markets and community celebrations creating a welcoming environment for all.

For those looking for a more budget-friendly option, October is an excellent choice. The crisp fall air and stunning autumn foliage provide a picturesque setting for exploration, with fewer crowds allowing for a more intimate experience. This month also offers fantastic opportunities for enjoying harvest festivals and local cuisine, showcasing the region's rich agricultural heritage.
What is the difference between a Windsor Bed and Breakfast and a hotel?
Every Windsor 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 Windsor B&Bs.

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