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Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
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Compare 2 B&B in Madison with updated reviews, rates, and availability.

The Lost Pearl
Exterior

The Lost Pearl

3.5 star property
9.8 out of 10, Exceptional, (44)
"It was a wonderful relaxing time spent there!! We were treated very well and the breakfast was delicious!! Definitely plan on going back!!"
$255 nightly
The price is $268
Jul 6 - Jul 7
Total includes taxes and fees
The Lost Pearl
The Caboose
Property grounds

The Caboose

9.4 out of 10, Exceptional, (3)
"So cute and the land was beautiful! Owners went above and beyond to make sure we had a wonderful stay 💜"
The Caboose
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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Frequently asked questions

What are the most popular Madison Bed and Breakfasts?
The Lost Pearl is a great choice for travelers seeking a great experience in Madison, boasting an impressive 9.8 rating. This charming B&B offers a delightful winery, complete with private and public tours that allow guests to immerse themselves in the local viticulture. With inviting balconies and patios, it's great for couples who want to relax with a glass of wine while enjoying beautiful views of the vineyard.
What is the nightly rate for a Bed and Breakfast in Madison?
Prices for B&Bs in Madison often vary, but you can find a great deal from $268 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Madison 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 Madison?
The best time to book a B&B in Madison is during the vibrant summer months, particularly from June through August. This period attracts travelers eager to immerse themselves in the city's lively atmosphere, marked by numerous festivals, outdoor activities, and cultural events. With warm temperatures averaging in the low to mid-80s Fahrenheit, it's an ideal time for exploring the stunning lakes, parks, and urban trails that Madison has to offer.

July stands out as the peak month, drawing both visitors and locals for events like the famous Concerts on the Square and the Dane County Fair. The warmth invites you to stroll along State Street, where you can enjoy local dining options and shop from unique boutiques while soaking up the sun.

If you're looking for a more budget-friendly experience, consider visiting in November. This quieter month offers a different charm as fall transitions into winter. You'll find fewer crowds, which allows for more leisurely exploration of Madison's museums and galleries, along with the opportunity to enjoy cozy cafes and the local culinary scene.
What is the difference between a Madison Bed & Breakfast and a hotel?
Every Madison 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 Madison B&Bs.