Holiday rentals with breakfast in Madison

Classic Madison home in walking distance to parks and lunch spots. Conveniently located near the isthmus, but in a family-friendly neighborhood, near parks with glacial land features.

Great space for all family members. Appreciated full kitchen and the electric kettle. Plenty of towels and the water was very hot. Would have liked to make use of back patio and fire pit, but weather precluded this. Jamie was very responsive and accommodating. We enjoyed our stay in Milton. Very much appreciated the seasonal goodies left for us. Thank you

We had a delightful stay here. The location could not be better. House is charming, clean, super open, great kitchen, lots of amenities. Paul was also super responsive and very helpful. Look forward to a return trip!

What a cool place to stay with lots of room, creative decor, and wonderful activities for all ages. My whole family enjoyed it.

We stayed for two night for my bachelor party. The house was very spacious and comfortable! The poker table was a huge hit and the area was amazing.

My husband and I planned a very impromptu trip to the driftless area with the hopes of including our adult son during our stay. Everything went amazingly smooth. Brian goes well above and beyond when it comes to hospitality. We did not lack for anything during our stay and in fact were surprised with many extras. Outdoor opportunities abound and each small town exhibits its own unique personality. Although the House on the Rock was a mind-blowing, portal traveling experience and worth every cent, Brian's house on the ridge was just as mind-blowing. The amenities, along with the beauty and peace provided the perfect setting to visit, reconnect over Scrabble (brought from home), and just hang out! Highly, highly recommend Brian's house on the ridge!

My family and I loved this lake home. Everything was just as pictured, and the home is very clean and spacious. There were 8 of us who stayed and there was plenty of room for everyone! We took advantage of the games and shuffleboard table upstairs. This location is a great getaway for a family to spend quality time together. Thank you Holly and Mike!

When girls' trip round 2 gets planned, we know where we are staying! Celeste and house were amazing and we can't thank her enough for the beautiful space. Plenty of sleep space, 2 clean bathrooms and a living that was the central hub for our card games and girl talk!

We had a wonderfully relaxing stay in this cozy, historic house. The place was exceptionally clean and thoughtfully stocked with snacks. The neighborhood was quiet, safe, and full of amenities within walking distance, making it a pleasure to explore. From the communication leading up to our stay to the smooth checkout process, everything about this experience was fantastic. I give it my highest recommendation!

Lori’s place was very nice, clean and cozy. The bed and the sofa were super comfortable. The kitchen was beautiful and stocked with the essentials. We felt comfortable and right at home. The game changer was the breakfast items and snacks that were available for us to eat. The fresh farm eggs, English muffins, OJ, milk, cereal, granola bars, butter, condiments and much more was a very kind and unique touch for an Air BnB. Oh and I can’t forget about the lovely note left for us wishing us a great stay and a Happy Anniversary. My husband and I felt right at home at Lori’s place 🥰❤️🥰

Always enjoy our stay at the upper half loft! Such a beautifully decorated apartment with everything you could need as a guest—the coffee machines are amazing, they have chargers in the bedrooms and the location is very walkable to downtown. We have stayed twice and will be back-

It was so unique and inviting! We will definitely be back! Great service and we felt very comfortable and very taken care of.

Really well appointed home. A lot of tastefully selected and placed decor items throughout the home. The place felt really warm and inviting and it was just what I needed after an extremely hectic day. And just this would’ve been more than enough for me. But the Beth hit it out of the park with her delicious breakfast. Catered to my specific dietary needs. Absolute scrumptious . And just what I needed before my 8 mile hike.

Our last minute stay with Deborah was fantastic! She was extremely accommodating with our late check-in, and made a delicious breakfast for us in the morning. The pool and hot tub were a big bonus we unfortunately did not get to take advantage of, but maybe next time! The suite we stayed in was pristine with a wonderful jacuzzi.

A great place to stay if just looking for a place to crash! They are planning to do some renovations soon and we definitely will be back to check them out . The parking situation was difficult but we found a parking garage about a 10 minute walk away and all was well. Overall we had a great stay and will be back :)

The Steampunk Many was an amazing stay! It had unique themes and creative ambience. The hosts were incredibly welcoming and mad us feel right at home! We will definitely be coming back here and bringing our friends! Thank you so much for welcoming us into your beautiful space :)

The Hosts were wonderful and it was exactly the respite I needed. For a true B &B experience I highly recommend the Rectory.

Steam Punk Manor is awyas a great place to stay. The rooms are amazingly decorated, the host is friendly and the breakfast in the morning is phenomenal.

Dorothy was so kind and flexible in our arrival. We enjoyed a beautiful fire in the evening and the room was so comfortable, cozy and clean. The farm area is so gorgeous and peaceful. Enjoyed our morning coffe on the front porch and she made pumpkin french toast for breakfast. A lovely getway that was very peaceful and a great value.