Wisconsin holiday rentals

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Best Wisconsin holiday rentals

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$0 - $530$530 - $1,060$1,060 - $1,591$1,591 - $2,119$2,119+ per night

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Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Wisconsin

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Menomonie Apartment: Walk to Lake Monomin! - Menomonie
Menomonie Apartment: Walk to Lake Monomin!
Menomonie, WI, United States
9.2Wonderful(10)
$178+
View availability
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe - Monticello - Living room
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Monticello, WI, United States
Free Wi-Fi
$274+
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Casa on the Red Cedar River - Menomonie - Patio
Casa on the Red Cedar River
Menomonie, WI, United States
Free Wi-Fi
$326+
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Wisco Wooded Retreat - Pewaukee
Wisco Wooded Retreat
Pewaukee, WI, United States
Pet-friendly
$407+
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MJ's Penthouse ,a piece of paradise on Monroe's historic square - Monroe - Living room
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Monroe, WI, United States
$414+
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Secluded cabin/house in woods - Brodhead
Secluded cabin/house in woods
Brodhead, WI, United States
Pool
Pet-friendly
$651+
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Main Street Sun Prairie Wi - 2 Bedroom - Sun Prairie - Living room
Main Street Sun Prairie Wi - 2 Bedroom
Sun Prairie, WI, United States
9.7Wonderful(10)
Parking
Free Wi-Fi
$675+
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Cannery Square Apartment 104 - Sun Prairie
Cannery Square Apartment 104
Sun Prairie, WI, United States
9.0Wonderful(1)
Parking
Free Wi-Fi
$704+
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Wisconsin Farmhouse Stay Utv, Boat, Snowmobile! - Monroe - Living room
Wisconsin Farmhouse Stay Utv, Boat, Snowmobile!
Monroe, WI, United States
Free Wi-Fi
Pet-friendly
$705+
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Beautiful downtown home, one block from the Square, - Monroe - Patio
Beautiful downtown home, one block from the Square,
Monroe, WI, United States
10Wonderful(20)
Free Wi-Fi
$775+
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Cannery Square Unit - 106 by Patriot Properties - Sun Prairie - Living room
Cannery Square Unit - 106 by Patriot Properties
Sun Prairie, WI, United States
Parking
Free Wi-Fi
$818+
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The Dairy at the Wegmueller Farm - stay on a Wisconsin farm! - Monroe - Outdoor view
The Dairy at the Wegmueller Farm - stay on a Wisconsin farm!
Monroe, WI, United States
$818+
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Updated Spacious Home Only 15 miles from PGA Open Erin Hills Golf Course - Sussex
Updated Spacious Home Only 15 miles from PGA Open Erin Hills Golf Course
Sussex, WI, United States
$838+
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Luxury Lake Geneva cottage w/hot tub on 2-acres - Delavan - Bedroom
Luxury Lake Geneva cottage w/hot tub on 2-acres
Delavan, WI, United States
Free Wi-Fi
$1,028+
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House For Rent- Eaa - Oshkosh - Living room
House For Rent- Eaa
Oshkosh, WI, United States
$1,201+
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Cozy & Quiet; Oshkosh Hidden Gem - Oshkosh - Dining room
Cozy & Quiet; Oshkosh Hidden Gem
Oshkosh, WI, United States
Free Wi-Fi
$2,201+
View availability
Useful Info

KAYAK’s insights for holiday rentals in Wisconsin

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Wisconsin with confidence.

What is the cheapest day of the week to book a vacation rental in Wisconsin?

Thursday offers the lowest rates in Wisconsin, with an average nightly price of $458. The highest prices are found on Wednesday, with average rates at $1,055.

How early should you book a vacation rental in Wisconsin?

Book at least 67 days before your stay begins to get the best price for your Wisconsin vacation rental.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
July
$484
$445
Cheapest month to stay with an average 25% drop in price.
Most expensive month to stay with an average 50% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding the perfect Wisconsin holiday rental

FAQs when booking a holiday home in Wisconsin

  • What is the most popular holiday rental destination in Wisconsin?

    Based on KAYAK holiday rental searches, the most popular destination is Milwaukee (100% of total searches to Wisconsin).

  • How much is a holiday rental in Wisconsin for tonight?

    In the last 72 hours, users have found Wisconsin holiday rentals for tonight for as little as $108. Search here for similar prices

  • How much is a holiday rental in Wisconsin for this weekend?

    In the last 72 hours, users have found Wisconsin holiday rentals for this weekend for as little as $130 per night. Search here for similar prices

  • What types of holiday rentals are available in Wisconsin?

    There are loads of different property types that you can make your holiday home in Wisconsin. You’ll find apartments, condos, houses, cabins, cottages, lodges, agritourism, villas, barns, campgrounds, caravan parks, campsites, homestays, chalets, houseboats, luxury tents and caravans.

  • What are some of the most-loved holiday rentals available in Wisconsin?

    If you’re looking for something special, the holiday rental most loved by KAYAK users is Great Wolf Lodge Wisconsin Dells.

  • Are there any pet-friendly holiday rentals in Wisconsin?

    There are a number of dog and pet-friendly Wisconsin holiday rentals, with around 12% allowing you to bring your pet along with you.

Where to stay in Wisconsin?

Our map will help you find the perfect place to stay in Wisconsin by showing you the exact location of each holiday home.

Everything you need to know for your stay in Wisconsin

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