Holiday Homes in South Madison

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Featured Holiday Homes in South Madison and around

Saddleback building features a brick facade and multiple windows on each floor.

"The property was beautiful, safe, and in a perfect location for the event we were attending!"

includes taxes & fees

1 Sept - 2 Sept

Relax in this serene room with a high ceiling, ceiling fan, and large window offering a view of the backyard and deck.

"The property was beautiful and our group of 8 had tons of space. It was beautiful and we wish we could’ve stayed longer. We would definitely stay there again. "

Two-story house with a garage on the ground floor, surrounded by a well-maintained lawn and stone wall.

"I had the pleasure of spending a short weekend at The Earthhouse BnB in Mt. Horeb, and it was absolutely wonderful! The property is tucked away in a serene, peaceful location that provided the perfect escape from the hustle and bustle of everyday life. The BnB itself is charming and cozy, with unique touches that made it feel like a true home away from home."

includes taxes & fees

24 Aug - 25 Aug

Stylish building surrounded by lush greenery, featuring a glass facade and brick architecture.

"This is our second stay and will gladly come back. It is easy to maneuver around Madison and the house is a spectacular vintage 80’s home. "

Relax by the serene lake with a fire pit and wooden dock, surrounded by lush greenery.

"Loved the lofted ceilings! Had everything we needed, including firewood. Can’t wait to come back"

Enjoy cooking in this kitchen with a large island and windows offering a view of the outdoors.

"We loved everything about this property. Would definitely stay there again."

includes taxes & fees

1 Sept - 2 Sept

"The Sun Prairie house perfectly met the goals for our family gathering of six adults and golden retriever for social and private space and so many entertainment options! The house was spotless, the neighborhood quiet, with Woodmans close by for shopping. We had 5 days of sunshine, golfing nearby courses, enjoying afternoon pool time, evening hot tub, and bug-free outdoor dining-so private and relaxing! We never ran out of room for food/drinks in the large volume fridge (loved the beverage...

Enjoy a meal at the kitchen island with a cutting board, or relax in the adjacent seating area with a view of the city skyline.

"Perfect for a weekend in Madison. A good location close to everything. "

includes taxes & fees

1 Sept - 2 Sept

Standing tall with a historic central dome, this building offers a glimpse into the past.

"Super clean, well lit, and beautiful view! Would definitely stay again."

includes taxes & fees

1 Sept - 2 Sept

Enjoy cooking in this well-equipped kitchen with a dishwasher, oven, and gas stove.

"Had a great stay!"

Enjoy cooking in this well-equipped kitchen with a microwave, coffee maker, and kettle.

"Prefect"

Relax on the inviting front porch with Adirondack chairs, surrounded by a serene garden and a tranquil water feature.

"It was so good to come back to a clean and cozy house each evening after spending the day at the World Dairy Expo."

Enjoy al fresco dining with a view of the surrounding landscape from this outdoor dining area featuring a table and chairs.

"Peaceful, quiet"

Relax on the deck overlooking the calm water, where you can soak in the hot tub or enjoy a drink at the bar.

"This rental made for the perfect group weekend getaway. From the great shuffleboard table to the vintage arcade games like NBA Jam, this place was on fire! The beautiful view of the wide river from the hot tub was so tranquil a member of our group asked what lake we were on. It’s the perfect distance from Madison and Chicago that you feel like you’ve truly gotten away, but close enough that lots of activities feel easily accessible. The house was clean and well stocked with everything needed to...

includes taxes & fees

11 Aug - 12 Aug

Relax on the patio with a sofa and two chairs, shaded by a covered area.

Enjoy a relaxing moment on the covered porch with a seating area and comfortable sofas.

"Oak House is a unique property ideally suited for family gatherings - this was our fourth stay. The house is roomy, well appointed, and decorated for the holidays. It also has access to nature trails for daily walks. The location has quiet privacy with quick access to activities in Madison. The property manager Rachel is very responsive. We highly recommend a stay here. "