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

Book Windsor Bed & Breakfast

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    We are not like the others - we include taxes and fees

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 brick building with a green awning, surrounded by colorful flowers and trees.

1. Hotel Ruby Marie

Hotel Ruby Marie
3.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (1,002 reviews)
"Great location. Loved the fireplace. Quaint, antique vibe but didn’t feel outdated. I’d stay here again."
United States
Kevin
$106 nightly
The price is $123
Nov 16 - Nov 17
Total with taxes and fees
Hotel Ruby Marie
A two-story house with multiple windows and a well-maintained lawn.

2. The Buckingham Inn

The Buckingham Inn
4.0 star property
Regent
10.0 out of 10, Exceptional, (44 reviews)
"Great experience, room, bathroom and breakfast just wonderful "
United States
Jose Luis
$246 nightly
The price is $284
Dec 16 - Dec 17
Total with taxes and fees
The Buckingham 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

AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

10/10 Excellent
"The room was super clean and pretty! Even the walls and floor were in great condition! I really loved how clean everything was. The bed was comfortable, the tv had a zillion channels, the bathroom was very clean, the elevator was clean, the pool was clean and warm! I loved the non-slip floor around the pool. The breakfast was pretty good too. I've stayed in many 3 and 4 star hotels in Madison, and this is a new favorite!"
Nicole 1-night trip
Posted 13 hours ago
AmericInn by Wyndham Madison West

Find out more about Windsor

Windsor B&B information

Number of reviews
44
Accommodation
3 B&B
Lowest Price
$123
Highest Price
$284

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 $123 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.

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