Wisconsin holiday rentals

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Best Wisconsin holiday rentals

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6+ Okay7+ Good8+ Great9+ Excellent

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$57 - $617$617 - $1,175$1,175 - $1,733$1,733 - $2,291$2,291+ per night

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ApartmentCondoHomestayHouse

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Free cancellationFree breakfastFree parkingFree internet

Most recommended holiday rentals in Wisconsin

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Homestay - Cat lovers welcome. I have a pool! - Milwaukee
Homestay - Cat lovers welcome. I have a pool!
Bay View
$57+
View availability
Washington Heights, Private Basement Room! - Milwaukee - Bathroom
Washington Heights, Private Basement Room!
Washington Heights
2.0Poor(1)
$92+
View availability
Econo Lodge Milwaukee Airport - Milwaukee - Bedroom
Econo Lodge Milwaukee Airport
Milwaukee, WI, United States
5.7Fair(797)
Free Wi-Fi
$98+
View availability
Homestay - Homestay - Awesome Upper Duplex in Bay View - Milwaukee
Homestay - Homestay - Awesome Upper Duplex in Bay View
Milwaukee, WI, United States
$104+
View availability
Flexhome Economy Studio Apt F1 - Milwaukee
Flexhome Economy Studio Apt F1
Milwaukee, WI, United States
8.0Very Good(10)
$119+
View availability
Econo Lodge Madison East - Madison - Bedroom
Econo Lodge Madison East
Madison, WI, United States
6.9Okay(679)
Parking
Free Wi-Fi
Pet-friendly
$121+
View availability
Queen Room With Two Queen Beds Non-Smoking - La Crosse - Bedroom
Queen Room With Two Queen Beds Non-Smoking
La Crosse, WI, United States
$164+
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Econo Lodge - La Crosse - Lobby
Econo Lodge
La Crosse, WI, United States
6.6Okay(463)
Parking
Free Wi-Fi
Pet-friendly
$172+
View availability
Cozy Home In Lake Geneva Wi Area - Lake Geneva - Living room
Cozy Home In Lake Geneva Wi Area
Lake Geneva, WI, United States
8.6Very Good(27)
Parking
Free Wi-Fi
$274+
View availability
Interlaken Villa Steps to Lodge Geneva National! - Lake Geneva
Interlaken Villa Steps to Lodge Geneva National!
Lake Geneva, WI, United States
9.4Wonderful(19)
Free Wi-Fi
Pool
$341+
View availability
The Perfect Getaway! Ground-Level Villa at The Lodge, formerly Interlaken. - Lake Geneva - Living room
The Perfect Getaway! Ground-Level Villa at The Lodge, formerly Interlaken.
Lake Geneva, WI, United States
9.2Wonderful(31)
Pool
$404+
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Modern 1BR Apt with Skywalk to Fiserv, Rooftop, and Parking - Milwaukee - Restaurant
Modern 1BR Apt with Skywalk to Fiserv, Rooftop, and Parking
Westown
8.7Very Good(40)
Parking
Free Wi-Fi
$413+
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Hidden Gem with Pool View! - Lake Geneva - Bedroom
Hidden Gem with Pool View!
Lake Geneva, WI, United States
9.8Wonderful(32)
Free Wi-Fi
Pool
$418+
View availability
Elegant 4-Season Lake Geneva Condo with Fireplace! - Lake Geneva
Elegant 4-Season Lake Geneva Condo with Fireplace!
Lake Geneva, WI, United States
9.5Wonderful(8)
Free Wi-Fi
Pool
$421+
View availability
Lake Geneva Gem: Luxury, Comfort & Prime Location - Lake Geneva - Living room
Lake Geneva Gem: Luxury, Comfort & Prime Location
Lake Geneva, WI, United States
9.5Wonderful(6)
$464+
View availability
Belleview House - Charming Pet-Friendly 3-Br Home, Backyard, Firepit - Milwaukee - Living room
Belleview House - Charming Pet-Friendly 3-Br Home, Backyard, Firepit
Milwaukee, WI, United States
9.4Wonderful(8)
Free Wi-Fi
$890+
View availability
Booking Insights

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?

Tuesday offers the lowest rates in Wisconsin, with an average nightly price of $407. The highest prices are found on Saturday, with average rates at $818.

How early should you book a vacation rental in Wisconsin?

Book at least 61 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)

November
December
$314
$573
Cheapest month to stay with an average 51% drop in price.
Most expensive month to stay with an average 1,274% 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 Oshkosh (50% of total searches to Wisconsin). The next most popular destination is Milwaukee (50%).

  • 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 $95. 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 $91 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, lodges, cottages, agritourism, villas, barns, campgrounds, campsites, homestays, caravans, chalets, houseboats and luxury tents.

  • 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 8% 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

Complete your trip to Wisconsin

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