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Featured Holiday Homes in Middleton

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

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

Monona
The price is AU$804 per night from 9 Dec to 10 Dec
AU$804
includes taxes & fees
9 Dec - 10 Dec
Located in Madison (Monona), this vacation home is within a 10-minute drive of University of Wisconsin-Madison and Alliant Energy Center.
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Arena
Located in Arena, this vacation home is on a river, within a 10-minute drive of Wisconsin River and Buckeridge's Home and Gallery.
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

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

Madison
With a stay at this vacation home in Madison, you'll be within a 10-minute drive of University of Wisconsin-Madison and Camp Randall Stadium.
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
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Legacy Guest House , Mount Horeb WI

Legacy Guest House , Mount Horeb WI

Mount Horeb
With a stay at this vacation home in Mount Horeb, you'll be within a 5-minute walk of Mount Horeb Chamber of Commerce Welcome Center and Mount Horeb Village ...
Legacy Guest House , Mount Horeb WI
A Pleasant Retreat- No Cleaning Fee & New Discounts

A Pleasant Retreat- No Cleaning Fee & New Discounts

Sun Prairie
With a stay at this vacation home in Sun Prairie, you'll be within a 10-minute walk of Sun Prairie Historical Library and Museum and Angell Park Speedway.
A Pleasant Retreat- No Cleaning Fee & New Discounts
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard

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

Middleton
Located in Middleton, this vacation home is in a rural location, a 3-minute drive from Penni Klein Dog Park and 6 minutes from Death's Door Spirits ...
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
Waterfront w/ HOT TUB + King Suite + Game Room

Waterfront w/ HOT TUB + King Suite + Game Room

Monona
Located in Madison (Monona), this vacation home is within a 10-minute drive of University of Wisconsin-Madison and Alliant Energy Center.
Waterfront w/ HOT TUB + King Suite + Game Room
ONE OF A KIND vacation rental with a view

ONE OF A KIND vacation rental with a view

Madison
With a stay at this vacation home in Madison, you'll be within a 10-minute drive of University of Wisconsin-Madison and Alliant Energy Center.
ONE OF A KIND vacation rental with a view
Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown

Madison
With a stay at this vacation home, you'll be centrally located in Madison, within a 5-minute drive of University of Wisconsin-Madison and Camp Randall ...
Doty ★ Walk to Everything -Hotel Quality- Downtown
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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.

Middleton 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 Middleton vacation homes are the perfect way for you to wing it.

Holiday houses in Middleton 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 Middleton 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 Middleton adventures, obvs.

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

Middleton Holiday Homes essential information

Accommodation
96 Holiday Homes
Lowest Price
AU$115
Highest Price
AU$804
Popular accommodation
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!, Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym, Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access, Legacy Guest House , Mount Horeb WI, A Pleasant Retreat- No Cleaning Fee & New Discounts, Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard, Waterfront w/ HOT TUB + King Suite + Game Room, ONE OF A KIND vacation rental with a view, Doty ★ Walk to Everything -Hotel Quality- Downtown

Top trending hotels in Middleton

Country Inn & Suites by Radisson, Madison West, WI

Country Inn & Suites by Radisson, Madison West, WI

2.5 out of 5
2212 Deming Way, Middleton, WI
Fully refundable
The price is AU$116 per night from 26 Dec to 27 Dec
AU$116
includes taxes & fees
26 Dec - 27 Dec
With a stay at Country Inn & Suites by Radisson, Madison West, WI, you'll be centrally located in Middleton, within a 15-minute drive of University of Wisconsin-Madison ...
Country Inn & Suites by Radisson, Madison West, WI
Fairfield Inn & Suites by Marriott Madison West/Middleton

Fairfield Inn & Suites by Marriott Madison West/Middleton

2.5 out of 5
8212 Greenway Blvd, Middleton, WI
Fully refundableReserve now, pay when you stay
The price is AU$115 per night from 20 Dec to 21 Dec
AU$115
includes taxes & fees
20 Dec - 21 Dec
Located in Middleton, Fairfield Inn & Suites by Marriott Madison West/Middleton is in the business district, a 3-minute drive from National Mustard Museum and ...
Fairfield Inn & Suites by Marriott Madison West/Middleton
Hilton Garden Inn Madison West/Middleton

Hilton Garden Inn Madison West/Middleton

3 out of 5
1801 Deming Way, Middleton, WI
Fully refundableReserve now, pay when you stay
The price is AU$173 per night from 26 Nov to 27 Nov
AU$173
includes taxes & fees
26 Nov - 27 Nov
A stay at Hilton Garden Inn Madison West/Middleton places you in the heart of Middleton, a 2-minute drive from National Mustard Museum and 11 minutes from University ...
Hilton Garden Inn Madison West/Middleton
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Courtyard by Marriott Madison West Middleton

Courtyard by Marriott Madison West Middleton

3 out of 5
2266 Deming Way, Middleton, WI
Fully refundableReserve now, pay when you stay
The price is AU$131 per night from 13 Dec to 14 Dec
AU$131
includes taxes & fees
13 Dec - 14 Dec
A stay at Courtyard by Marriott Madison West Middleton places you in the heart of Middleton, within a 15-minute drive of University of Wisconsin-Madison and ...
Courtyard by Marriott Madison West Middleton
Don't see what you're looking for?
See all available properties in Middleton
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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.