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

Book Windsor Bed & Breakfast

Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Windsor bed & breakfast

Miscellaneous

1. Hotel Ruby Marie

Hotel Ruby Marie
3.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (1,007 reviews)
"What a charming and well-located alternative to chain lodging. Will totally stay here again on our next overnight to Madison. Property was well maintained, check-in was awesome."
United States
Laurie
$110 nightly
The price is $127
Sep 3 - Sep 4
Total with taxes and fees
Hotel Ruby Marie
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

8/10 Good
"The hotel was clean. The staff was very kind and helpful. The bed was a little like a soup bowl, good thing it was a king and we had plenty of room! There were some interesting characters hanging around outside. We still felt safe, just noticed them."
Bret 2-night trip
Posted 2 hours ago
Baymont by Wyndham Madison West/Middleton WI West

Find out more about Windsor

Windsor B&B information

Number of reviews
Accommodation
3 B&B
Lowest Price
$127
Highest Price
$127

Frequently asked questions

What is the nightly rate for a Bed & 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 B&B in Windsor?
The best time to book a B&B in Windsor is during the vibrant summer months, particularly from June to August. This peak season welcomes travelers eager to explore the stunning vineyards, participate in outdoor festivals, and enjoy the warm, inviting climate that characterizes this charming area. With temperatures typically ranging from the mid-70s to low 90s Fahrenheit, it's an ideal setting for leisurely strolls through the picturesque countryside or savoring local wines on your favorite patio.

July stands out as the highlight of the season, drawing visitors with its lively atmosphere and numerous events. During this month, you can immerse yourself in local culture at farmers' markets or enjoy live music events that showcase the best of Windsor's artistic flair.

For those looking for a more budget-friendly experience, consider visiting in December. While this month may be quieter, it offers a unique charm with holiday decorations, cozy gatherings, and special winter-themed events that highlight the town's community spirit.
What is the difference between a Windsor B&B 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.

Explore a world of travel with Expedia