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Next weekend
Aug 22 - Aug 24
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Aug 29 - Aug 31
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B&B in Madison

The Caboose
Property grounds

The Caboose

9.6 out of 10, Exceptional, (4)
"We enjoyed staying the weekend in The Caboose. My husband would have enjoyed a love seat inside to sit and watch tv versus lying in bed but, it is a little place to rest your head and shower and get on with adventures. I love the outdoors and having a fire in the evening. Easy drive to a plethora of wineries. In the summer do not turn the AC down no matter what. We were comfortable and had a wonderful time."
$269 nightly
The price is $280
Aug 17 - Aug 18
Total includes taxes and fees
The Caboose
The Willoughby House
Terrace/patio

The Willoughby House

3.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful property. Nice location. Excellent lounge & restaurant."
$211 nightly
The price is $243
Aug 17 - Aug 18
Total includes taxes and fees
The Willoughby House
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 Madison Hotel Reviews

Red Roof Inn Cleveland - Mentor/ Willoughby

Red Roof Inn Cleveland - Mentor/ Willoughby

10/10 Excellent
"Great location right by the highway exit. Staff was friendly and accommodating. We drove from Cleveland Airport. Friendly staff! :) Keep up the good work! Mentor is a bigger city just 10 minutes away. Great options for restaurants and grocery stores. Too bad they didn't have a mini-fridge in the room. It would make our life easier, as we had medication that was temperature controlled. We were there for two nights visiting Kirtland's Historic Sites. It was boiling hot outside (July/2025), but the AC worked really well. Ice machine was helpful, but a mini-fridge in the room would make a huge difference. Thanks."
Luzia 2-night trip
Posted 1 day ago
Red Roof Inn Cleveland - Mentor/ Willoughby

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 $280 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.