Holiday Homes in Madison

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Featured Holiday Homes in Madison

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

9.8 out of 10, Exceptional, (29)
"We needed a rental for our employees to stay at while working at a job in the area. This unit was perfect as men usually don't mind sharing a room but not a bed and this unit had separate beds for our 5 employees. They enjoyed the comforts of home while away from their families. Jake was helpful and provided all the information we needed and made check in and checkout very simple. We had to book in weekly intervals and they were able to accommodate this type of booking which was very helpful."
The price is AU$814
includes taxes & fees
2 Dec - 3 Dec
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Conveniently Located just off University Avenue on Madison's West Side

10.0 out of 10, Exceptional, (117)
"We were here for the PSU- Wisconsin game and the house worked great. Maybe just a new shower curtain liner in the upstairs bathroom 😁"
Conveniently Located just off University Avenue on Madison's West Side

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

10.0 out of 10, Exceptional, (98)
"Beautiful space, very relaxing. We had a great stay!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

Legacy Guest House , Mount Horeb WI

10.0 out of 10, Exceptional, (51)
"The property was as advertised. It was cute and made good use of the space available. Not overly spacious but we were comfortable with four adults. The “rules” were very clearly posted and were more than reasonable. The only feedback I would give is that it didn’t appear to have the floors well swept and countertops wiped, nor the toilets cleaned. However, they weren’t filthy by any means. Just needed to have a quick cleanup. The linens were all nice and easily accessible. We would stay again. "
Legacy Guest House , Mount Horeb WI

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (215)
"This house was perfect for me and my adult son and daughter. We all had or own bed, the house was clean and comfortable and we absolutely loved the style of the older homes in the neighborhood. Every you could want was close by and the host was amazing. "
A Pleasant Retreat- No Cleaning Fee & New Discounts

Log home Lake Koshkonong and Rock River !

10.0 out of 10, Exceptional, (25)
"Very relaxing and peaceful!! Home was very spacious!!"
Log home Lake Koshkonong and Rock River !

Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard

10.0 out of 10, Exceptional, (142)
"We have stayed multiple times, and always enjoy the country setting; cleanliness; well equipped, large kitchen; nearby dog park; and wonderful hosts. "
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard

Waterfront w/ HOT TUB + King Suite + Game Room

9.6 out of 10, Exceptional, (25)
"Fantastic place, very clean and great location. We will book this place again. "
Waterfront w/ HOT TUB + King Suite + Game Room

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (129)
"Awesome stay with Son and Grandsons. Great place to stay."
ONE OF A KIND vacation rental with a view

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (29)
"When I was enrolled at UW-Madison, I lived blocks from The Doty and would have loved to live at this adorable 3-bed home! It is well maintained and really did suit our location needs, near the Overture Center. Located in student rental neighborhood, I was worried it might be loud but we slept well. The beds were very comfortable. Plenty of pillows and blankets provided. We did not use the kitchen but it seemed well stocked. Had a wonderful breakfast at Marigold Kitchen. Two things I would...
Doty ★ Walk to Everything -Hotel Quality- Downtown

Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path

10.0 out of 10, Exceptional, (24)
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Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path

Family-Friendly Lake Waubesa Home: Boat + Swim!

9.8 out of 10, Exceptional, (8)
"We were there at the start of fall and the gas fireplaces were awesome both for the ambiance and warmth on cooler days. The view from the sunroom was wonderful. We spent a lot of time enjoying the view from there. It had a nice mix of modern amenities (updated kitchen and baths) and rustic charm. The neighborhood was very cute. We walked our dog quite a bit and enjoyed views of the lake side homes and the lake from all around the house. Plus there are two parks both within walking distance...
Family-Friendly Lake Waubesa Home: Boat + Swim!

Studio queen with views of Lake Monona in the heart of downtown Madison

9.0 out of 10, Wonderful, (4)
"Was in town for UWM parents weekend and wanted something more than a simple hotel room as I was going to be there for nearly a week. The Saddlery for the bill. Location was amazing. Having a kitchenette meant I could fully enjoy the great farmers market that weekend. And the view out my window of the lake was a perfect way to wake up. Manager was very responsive. Everything was as stated. TV/media set up would benefit from updating, but it actually didn’t matter as it allowed me to tuck into a...
The price is AU$464
includes taxes & fees
30 Nov - 1 Dec
Studio queen with views of Lake Monona in the heart of downtown Madison

Relax on the Sugar River in this beautiful newly renovated building

2.0 star property
10.0 out of 10, Exceptional, (10)
"Beautiful set up enough room for everyone and great time, 10/10 place would recommend"
Relax on the Sugar River in this beautiful newly renovated building

Eagle's Landing on the Rock River, Pontoon available for additional fee

10.0 out of 10, Exceptional, (10)
"Great property! Want to return next summer for a family vacation."
Eagle's Landing on the Rock River, Pontoon available for additional fee

Adorable home w lake front- Paddle boats & kayaks ava, and 2 bathrooms!

9.8 out of 10, Exceptional, (145)
"We have been coming here for several years and love it. Super quiet neighborhood, home is clean and well maintained, Tammy is a great host and quick to answer messages. We will be back again next year!"
Adorable home w lake front- Paddle boats & kayaks ava, and 2 bathrooms!

Book Xmas & Winter Now! Fireplace/Arcade/PingPong

10.0 out of 10, Exceptional, (13)
"Cool place with nice amenities. Only complaint is the fan needs to be repaired in the front bedroom. But everything was great. "
Book Xmas & Winter Now! Fireplace/Arcade/PingPong

Updated home with lake views-near Ferry, Devil's Lake, and 30 min to WI Dells!

10.0 out of 10, Exceptional, (26)
"Perfect home base for a two-family vacay. Four teenage boys and two moms and we never felt crowded. Easy drive to the Dells, Devil’s Lake, and Baraboo. Beautiful views of Lake WI from the deck and a quick walk to fishing at Memorial park and ice cream at the ferry crossing. The house was very clean, stocked with basics, and communication with the owner was so easy. Highly recommend!"
Updated home with lake views-near Ferry, Devil's Lake, and 30 min to WI Dells!

HOT TUB - 20 min to Capitol - KING Bed - Fireplace

10.0 out of 10, Exceptional, (5)
"My adult children (including SIL) and my partner and I wanted to visit Madison for the first time. While the house is a little further from downtown (20 mins.) than we might have liked, it was worth it for the size, comfort and cleanliness of the house. We had plenty of room and all of the necessities. We pretty much just slept and had breakfast at the house, but it would've been great if we'd needed to spend more time there. (I was looking forward to using the hot tub and Pacman machine,...
HOT TUB - 20 min to Capitol - KING Bed - Fireplace

'Rock River Retreat' w/ Dock & Private Backyard!

10.0 out of 10, Exceptional, (12)
"House was great for our group. 4 kiddos and 5 adults. Lots of nice extras at house. Pool was great for the kiddos. Beds very comfy! Big bedroom great for a family with kiddos that can sleep safely in bunks. Other bedroom attached directly to it for parents and kiddos in pack n play but could prove awkward for groups not wanting others traipsing through the attached bedrooms to go outside to pool or use the second bathroom. House was clean and well equipped . Would def go back.bedrooms "
'Rock River Retreat' w/ Dock & Private Backyard!
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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Other property types in Madison

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

9.8 out of 10, Exceptional, (29)
"We needed a rental for our employees to stay at while working at a job in the area. This unit was perfect as men usually don't mind sharing a room but not a bed and this unit had separate beds for our 5 employees. They enjoyed the comforts of home while away from their families. Jake was helpful and provided all the information we needed and made check in and checkout very simple. We had to book in weekly intervals and they were able to accommodate this type of booking which was very helpful."
The price is AU$814
includes taxes & fees
2 Dec - 3 Dec
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Conveniently Located just off University Avenue on Madison's West Side

10.0 out of 10, Exceptional, (117)
"We were here for the PSU- Wisconsin game and the house worked great. Maybe just a new shower curtain liner in the upstairs bathroom 😁"
Conveniently Located just off University Avenue on Madison's West Side

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

10.0 out of 10, Exceptional, (98)
"Beautiful space, very relaxing. We had a great stay!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.