Book Holiday Homes in Madison

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Featured Holiday Homes in Madison

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

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

Verona WI
Stay at this family-friendly holiday home in Verona. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Goodman Aquatic Center and Dane County ...
Opens in a new window Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail
On the Yahara River, access to Madison Lakes

On the Yahara River, access to Madison Lakes

Monona WI
Stay at this holiday home in Madison. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Alliant Energy Center and Camp Randall ...
Opens in a new windowOn the Yahara River, access to Madison Lakes
Beautifully remodeled 2 bed 104 Berkley Verona #6

Beautifully remodeled 2 bed 104 Berkley Verona #6

Verona WI
Stay at this holiday home in Verona. Enjoy air conditioning. Popular attractions Fireman's Beach and Verona Ice Arena are located nearby.
Opens in a new windowBeautifully remodeled 2 bed 104 Berkley Verona #6
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The EarthHouse  ~  Wall-to-wall unique style, Luxury Linens and Amazing Comfort

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

Mount Horeb WI
The price is NZ$377 per night from 12 May to 13 May
NZ$377
12 May - 13 May
includes taxes & fees
Stay at this golf holiday home in Mount Horeb. Enjoy free Wi-Fi, an in-room coffee maker and air conditioning. Popular attractions Mt. Horeb Area Museum and ...
Opens in a new windowThe EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Cozy Cabin in The Driftless

Cozy Cabin in The Driftless

Cross Plains WI
Stay at this family-friendly holiday home in Cross Plains. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions Cross Plains State ...
Opens in a new windowCozy Cabin in The Driftless
Plan your reunion/gathering now in beautiful rural South Central Wisconsin

Plan your reunion/gathering now in beautiful rural South Central Wisconsin

Cambridge WI
Stay at this family-friendly holiday home in Deerfield. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowPlan your reunion/gathering now in beautiful rural South Central Wisconsin
Private Pool - Hot Tub - Game Room - 20 min DT

Private Pool - Hot Tub - Game Room - 20 min DT

Sun Prairie WI
Stay at this family-friendly holiday home in Sun Prairie. Enjoy private pools, a water park and breakfast (surcharge). Popular attractions Sun Prairie Historical ...
Opens in a new windowPrivate Pool - Hot Tub - Game Room - 20 min DT
220’ WATERFRONT BEACH HOME ROCK RIVER WI PETS PIER POOLS FP FISHNG BOAT KAYAKS

220’ WATERFRONT BEACH HOME ROCK RIVER WI PETS PIER POOLS FP FISHNG BOAT KAYAKS

Edgerton WI
Stay at this beach holiday home in Edgerton. Enjoy free Wi-Fi, private pools and a beach locale. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new window220’ WATERFRONT BEACH HOME ROCK RIVER WI PETS PIER POOLS FP FISHNG BOAT KAYAKS
A Pleasant Retreat

A Pleasant Retreat

Sun Prairie WI
Stay at this family-friendly holiday home in Sun Prairie. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the helpful staff and the property ...
Opens in a new windowA Pleasant Retreat
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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.

Madison Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Madison vacation homes are the perfect way for you to wing it.

Holiday houses in Madison let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Madison in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Madison adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Madison with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Madison vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Madison Holiday Homes essential information

Accommodation
148 Holiday Homes
Lowest Price
NZ$155
Highest Price
NZ$377
Popular accommodation
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail, On the Yahara River, access to Madison Lakes, Beautifully remodeled 2 bed 104 Berkley Verona #6, The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort , Cozy Cabin in The Driftless, Plan your reunion/gathering now in beautiful rural South Central Wisconsin, Private Pool - Hot Tub - Game Room - 20 min DT, 220’ WATERFRONT BEACH HOME ROCK RIVER WI PETS PIER POOLS FP FISHNG BOAT KAYAKS, A Pleasant Retreat

Top trending hotels in Madison

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is NZ$243 per night from 24 May to 25 May
NZ$243
24 May - 25 May
includes taxes & fees
Stay at this luxury hotel in Madison. Enjoy free Wi-Fi, breakfast (surcharge) and a free airport shuttle. Our guests praise the breakfast and the pool in their ...
Opens in a new windowThe Madison Concourse Hotel and Governor's Club
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
The price is NZ$189 per night from 24 May to 25 May
NZ$189
24 May - 25 May
includes taxes & fees
Stay at this business-friendly hotel in Madison. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Opens in a new windowDoubleTree by Hilton Madison East
Tru by Hilton Madison West, WI

Tru by Hilton Madison West, WI

2.5 out of 5
8102 Watts Rd. Madison WI
Fully refundableReserve now, pay when you stay
The price is NZ$155 per night from 18 May to 19 May
NZ$155
18 May - 19 May
includes taxes & fees
Stay at this business-friendly hotel in Madison. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
Opens in a new windowTru by Hilton Madison West, WI
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Best Western East Towne Suites

Best Western East Towne Suites

2.5 out of 5
4801 Annamark Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is NZ$165 per night from 10 May to 11 May
NZ$165
10 May - 11 May
includes taxes & fees
Stay at this business-friendly hotel in Madison. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowBest Western East Towne Suites
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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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^Subject to availability and chosen travel dates.