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

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Our top choices for Windsor bed & breakfast

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
$129 nightly
The price is $148
Aug 31 - Sep 1
Total with taxes and fees
Calistoga Wine Way Inn

2. 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
$293 nightly
The price is $340
Aug 31 - Sep 1
Total with taxes and fees
Healdsburg Inn on the Plaza, A Four Sisters Inn

3. 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

4. Highland Dell Lodge

Highland Dell Lodge
3.0 star property
Monte Rio
9.2 out of 10, Wonderful, (646 reviews)
"Love this place… beautiful location, excellent stay, clean, great food in the restaurant, staff are very nice! Highly recommend!"
United States
Renee
$176 nightly
The price is $200
Sep 16 - Sep 17
Total with taxes and fees
Highland Dell Lodge

5. Boon Hotel + Spa - Adults Only

Boon Hotel + Spa - Adults Only
3.0 star property
Guerneville
9.8 out of 10, Exceptional, (69 reviews)
"Amazing vacation vibe, great breakfast, and incredibly convenient place to relax and enjoy."
United States
Thomas
$286 nightly
The price is $326
Sep 2 - Sep 3
Total with taxes and fees
Boon Hotel + Spa - Adults Only

6. Inn at Occidental

Inn at Occidental
3.5 star property
Occidental
9.2 out of 10, Wonderful, (509 reviews)
"We really enjoyed our time here. They had live music on the outdoor patio both nights we were there. The breakfast was really good too. We would stay here again."
United States
NICCOLE
$230 nightly
The price is $262
Sep 16 - Sep 17
Total with taxes and fees
Inn at Occidental

7. Sonoma Holiday Escape • 1BR Queen • Near Wineries

Sonoma Holiday Escape • 1BR Queen • Near Wineries
Santa Rosa
$316 nightly
The price is $352
Sep 16 - Sep 17
Total with taxes and fees
Sonoma Holiday Escape • 1BR Queen • Near Wineries

8. 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

9. The Gables Wine Country Inn

The Gables Wine Country Inn
5.0 star property
Santa Rosa
10.0 out of 10, Exceptional, (26 reviews)
"Very comfortable staying. My girlfriend and I stayed two nights. We really enjoyed our time at the Gables Inn. The property was enjoyable to walk around. Pam and Larry were as hospitable as I’ve experienced. The breakfast was a 10! Fantastic and enjoyable. Loved our stay!!"
United States
Brad
$276 nightly
The price is $314
Sep 29 - Sep 30
Total with taxes and fees
The Gables Wine Country Inn

10. 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
Aug 30 - Aug 31
Total with taxes and fees
Chateau De Vie

11. Camellia Inn

Camellia Inn
3.5 star property
Healdsburg
8.6 out of 10, Excellent, (623 reviews)
"Nice place to stay for the weekend, close to town"
United States
Robb
$362 nightly
The price is $420
Aug 30 - Aug 31
Total with taxes and fees
Camellia Inn

12. 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

13. 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

14. 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

15. 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

16. Beltane Ranch

Beltane Ranch
4.0 star property
Glen Ellen
9.8 out of 10, Exceptional, (117 reviews)
"Such a lovely hidden gem in Sonoma! The room was pretty, breakfast was excellent, the staff super nice and helpful. We loved our stay here and will come back for sure! "
United States
Tanja
$478 nightly
The price is $545
Aug 30 - Aug 31
Total with taxes and fees
Beltane Ranch

17. Craftsman Inn

Craftsman Inn
3.5 star property
Calistoga
9.2 out of 10, Wonderful, (269 reviews)
"Very comfortable nice room"
United States
Chanynn
$177 nightly
The price is $203
Aug 30 - Aug 31
Total with taxes and fees
Craftsman Inn

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

Mine + Farm, The Inn at Guerneville, CA
3.5 star property
Guerneville
9.0 out of 10, Wonderful, (152 reviews)
"Beautiful property, great location, delicious breakfast. "
United States
Amy
$397 nightly
The price is $452
Aug 30 - Aug 31
Total with taxes and fees
Mine + Farm, The Inn at Guerneville, CA
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

Find out more about Windsor

Windsor B&B information

Number of reviews
4,063
Accommodation
48 B&B
Lowest Price
$148
Highest Price
$8,062

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 $148 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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