Holiday Homes in South Madison

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in South Madison and around

Two bedroom suite with city views in the heart of downtown Madison
Fridge, microwave, oven, stovetop

Two bedroom suite with city views in the heart of downtown Madison

9.8 out of 10, Exceptional, (33)
"Perfect for a weekend in Madison. A good location close to everything. "
The price is €390
includes taxes & fees
1 Sept - 2 Sept
Two bedroom suite with city views in the heart of downtown Madison
Two Bedroom with views of Lake Monona in the heart of downtown Madison
Interior

Two Bedroom with views of Lake Monona in the heart of downtown Madison

10.0 out of 10, Exceptional, (7)
"We loved everything about this property. Would definitely stay there again."
The price is €414
includes taxes & fees
1 Sept - 2 Sept
Two Bedroom with views of Lake Monona in the heart of downtown Madison
Adorable home w lake front- Paddle boats & kayaks ava, and 2 bathrooms!
Terrace/patio

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

9.8 out of 10, Exceptional, (160)
"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!
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Outdoor spa tub

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

10.0 out of 10, Exceptional, (115)
"I was visiting from Chicago for a concert and was immediately sold with this property! I loved the hot tub and fireplace!! The whole house was clean and very bright! I will definitely stay again!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Charming 4-bedroom bungalow in lovely Fort Atkinson near Lake
Interior

Charming 4-bedroom bungalow in lovely Fort Atkinson near Lake

Charming 4-bedroom bungalow in lovely Fort Atkinson near Lake
YOUR DREAM GETAWAY 220’ WATERFRONT BEACH HOUSE ROCK RIVER WI FP POOL PIER KAYAKS
Property grounds

YOUR DREAM GETAWAY 220’ WATERFRONT BEACH HOUSE ROCK RIVER WI FP POOL PIER KAYAKS

9.8 out of 10, Exceptional, (162)
"Loved the lofted ceilings! Had everything we needed, including firewood. Can’t wait to come back"
YOUR DREAM GETAWAY 220’ WATERFRONT BEACH HOUSE ROCK RIVER WI FP POOL PIER KAYAKS
Remodeled home with pontoon rental 2 decks Private beach playground volleyball
Fridge, microwave, oven, stovetop

Remodeled home with pontoon rental 2 decks Private beach playground volleyball

10.0 out of 10, Exceptional, (3)
"We really enjoyed this house! Short walk to the beautiful lake. Friendly neighbors and lots of wildlife in the area. The house had plenty of room for everyone and everything we needed for the week. Will definitely stay here again when in the area!"
Remodeled home with pontoon rental 2 decks Private beach playground volleyball
Private Pool - HOT TUB - Sauna - Game Room - Pets
Terrace/patio

Private Pool - HOT TUB - Sauna - Game Room - Pets

10.0 out of 10, Exceptional, (1)
"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...
Private Pool - HOT TUB - Sauna - Game Room - Pets
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail
Smart TV, fireplace, video games, DVD player

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

9.6 out of 10, Exceptional, (61)
"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. "
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail
Spacious & Modern Home w/ Deck in Oregon!
Fridge, microwave, stovetop, dishwasher

Spacious & Modern Home w/ Deck in Oregon!

7.0 out of 10, Good, (2)
"Awesome...very clean property.Plenty of space for eight people...Quiet neighborhood"
Spacious & Modern Home w/ Deck in Oregon!
Beautifully updated home close to downtown New Glarus
Exterior detail

Beautifully updated home close to downtown New Glarus

10.0 out of 10, Exceptional, (58)
"It was so good to come back to a clean and cozy house each evening after spending the day at the World Dairy Expo."
Beautifully updated home close to downtown New Glarus
Beautifully styled, Mid Century Modern, family friendly Lake Mills House!
Property grounds

Beautifully styled, Mid Century Modern, family friendly Lake Mills House!

9.8 out of 10, Exceptional, (15)
"We loved the house, location, and owners. "
Beautifully styled, Mid Century Modern, family friendly Lake Mills House!
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
Exterior

One Bedroom King with Den with views of Lake Monona in the heart of downtown.

9.6 out of 10, Exceptional, (27)
"The property was beautiful, safe, and in a perfect location for the event we were attending!"
The price is €331
includes taxes & fees
1 Sept - 2 Sept
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
Right on the Water! Private Pier, Excellent Sunsets & Swimming
Outdoor dining

Right on the Water! Private Pier, Excellent Sunsets & Swimming

9.4 out of 10, Exceptional, (101)
"Some things to note - 2 bedrooms with nice bed 1 bed in a loft upstairs not as private as a bedroom and then ( this "
Right on the Water! Private Pier, Excellent Sunsets & Swimming
One Bedroom King with Den with views of the heart of downtown.
Exterior

One Bedroom King with Den with views of the heart of downtown.

2.0 star property
10.0 out of 10, Exceptional, (23)
"Super clean, well lit, and beautiful view! Would definitely stay again."
The price is €319
includes taxes & fees
1 Sept - 2 Sept
One Bedroom King with Den with views of the heart of downtown.
Lakeside Retreat at Lake Ripley - Swimming, Dock, Kayaks, & PONTOON RENTAL
Outdoor dining

Lakeside Retreat at Lake Ripley - Swimming, Dock, Kayaks, & PONTOON RENTAL

10.0 out of 10, Exceptional, (31)
"Peaceful, quiet"
Lakeside Retreat at Lake Ripley - Swimming, Dock, Kayaks, & PONTOON RENTAL
Waterfront - Hot Tub - Sauna - Game Room - Pets
Outdoor spa tub

Waterfront - Hot Tub - Sauna - Game Room - Pets

10.0 out of 10, Exceptional, (1)
"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...
Waterfront - Hot Tub - Sauna - Game Room - Pets
ONE OF A KIND vacation rental with a view
Exterior

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (139)
"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. "
ONE OF A KIND vacation rental with a view
Paoli Den - Newly Remodeled!
Fridge, microwave, oven, stovetop

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (21)
"Prefect"
Paoli Den - Newly Remodeled!
A Pleasant Retreat- No Cleaning Fee & New Discounts
Property grounds

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (240)
"This home was perfect for our family and was so cute and clean. But the owners are what made it so special. They greeted us and showed us around the house. They made sure you felt at home. "
A Pleasant Retreat- No Cleaning Fee & New Discounts
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 South Madison Hotel Reviews

Days Inn & Suites by Wyndham Madison

Days Inn & Suites by Wyndham Madison

10/10 Excellent
"Close to all the places we wanted to go and is a very quiet place to stay."
Gabriella 3-night trip
Posted 5 hours ago
Days Inn & Suites by Wyndham Madison