Southeast Wisconsin holiday rentals

We found 2,404 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southeast Wisconsin

Showing deals for:8 Jan - 15 Jan

Pool
Living area
Dining
Private kitchen
Exceptional
(13 reviews)

Kohl Manor Luxury Lake 8br year round retreat Pool, Cinema, Arcade on LacLaBelle

Oconomowoc

9% off
AU$35,184
for 7 nights, 1 home
AU$5,026 per night
includes taxes & fees
Kohl Manor Luxury Lake 8br year round retreat Pool, Cinema, Arcade on LacLaBelle
Sitting area
Attic balcony
Private kitchen
Exterior
Exceptional
(22 reviews)

Lakefront Haven: Waterfront Oasis with Dock, Spacious Swim Pier & Pano Lake view

Delavan

8% off
AU$10,618
for 7 nights, 1 cottage
AU$1,517 per night
includes taxes & fees
Lakefront Haven: Waterfront Oasis with Dock, Spacious Swim Pier & Pano Lake view
Kitchen and sitting area
Exterior
Exterior
Front room sitting area
Exceptional
(43 reviews)

Stunning Lakeside Retreat: Delavan Lake Home with Lake Views & Lake Access

Delavan

8% off
AU$8,529
for 7 nights, 1 home
AU$1,218 per night
includes taxes & fees
Stunning Lakeside Retreat: Delavan Lake Home with Lake Views & Lake Access
Exterior
Property grounds
Living area
Living area
Exceptional
(16 reviews)

Serene 4-bedroom Lake House in Pewaukee-Hot Tub!

Pewaukee

8% off
AU$10,397
for 7 nights, 1 home
AU$1,485 per night
includes taxes & fees
Serene 4-bedroom Lake House in Pewaukee-Hot Tub!
Exterior
Exterior
Dining
Living area
Exceptional
(7 reviews)

Brand New Lakeview Retreat: Beautiful Delavan Lake Views & Private Lake Access

Delavan

8% off
AU$10,568
for 7 nights, 1 home
AU$1,510 per night
includes taxes & fees
Brand New Lakeview Retreat: Beautiful Delavan Lake Views & Private Lake Access
Private kitchen
Exterior
Dining
Exterior
Exceptional
(45 reviews)

THE ULTIMATE LAKEHOUSE

Lake Geneva

17% off
AU$11,038
for 7 nights, 1 home
AU$1,577 per night
includes taxes & fees
THE ULTIMATE LAKEHOUSE
16 feet of dining that can be expanded to add another 8 feet
Great spot for  your morning coffee
Living area
Exterior
Exceptional
(112 reviews)

Private Country House near Lake Geneva, Como and Williams Bay

Lake Geneva

8% off
AU$14,854
for 7 nights, 1 home
AU$2,122 per night
includes taxes & fees
Private Country House near Lake Geneva, Como and Williams Bay
Outdoor dining
Exterior detail
Living area
Private kitchen
Exceptional
(98 reviews)

Great for large groups, sleeps 20 , Fontana on Geneva Lake

Fontana

8% off
AU$9,637
for 7 nights, 1 home
AU$1,377 per night
includes taxes & fees
Great for large groups, sleeps 20 , Fontana on Geneva Lake
table for 10
Property grounds
Dining
well built and only 15 years old
Wonderful
(61 reviews)

🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲

Twin Lakes

8% off
AU$7,218
for 7 nights, 1 home
AU$1,031 per night
includes taxes & fees
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
New 2nd story addition with permanent gas grill.
Comfy seating area in 3 season room overlooking the lake.
Living room with cast iron stove panoramic  lake views
Screen and window 3 season room with cozy ceiling heating and panoramic views.
Exceptional
(158 reviews)

Island view cottage on crystal clear spring fed lake.

Burlington

6% off
AU$7,017
for 7 nights, 1 home
AU$1,002 per night
includes taxes & fees
Island view cottage on crystal clear spring fed lake.
work space office
lake and beach front home
main front deck
living area
Exceptional
(47 reviews)

LAKEFRONT HIDDEN GEM !

Elkhorn

12% off
AU$5,285
for 7 nights, 1 home
AU$755 per night
includes taxes & fees
LAKEFRONT HIDDEN GEM !
Cozy cabin-style home surrounded by mature trees and outdoor space, offering a private and relaxed setting for your Lake Geneva getaway.
Large screened porch with dining space, lounge seating, and peaceful wooded views for relaxing in every season.
Bright sunroom with lounge seating, natural light, and a full laundry area for added comfort during longer stays.
Open living room with comfortable seating, natural light, and space to gather after lake days, cozy winter weekends, and evenings by the fire.
Exceptional
(6 reviews)

Lake Geneva Escape with Arcade, Fire Pit and Deck

Lake Geneva

6% off
AU$3,618
for 7 nights, 1 home
AU$517 per night
includes taxes & fees
Lake Geneva Escape with Arcade, Fire Pit and Deck
Room
Property grounds
Dining
Living area
Exceptional
(26 reviews)

Luxury Lake Geneva House, Heated Pool, 2 Hot Tubs, Sauna, Fire Pit, Photo Zone

Lake Geneva

8% off
AU$27,513
for 7 nights, 1 home
AU$3,930 per night
includes taxes & fees
Luxury Lake Geneva House, Heated Pool, 2 Hot Tubs, Sauna, Fire Pit, Photo Zone
Exterior
Lobby
Pool
Private kitchen
Exceptional
(12 reviews)

South Elder Acres: Log Cabin w/ Indoor Pool

Lake Geneva

8% off
AU$15,233
for 7 nights, 1 home
AU$2,176 per night
includes taxes & fees
South Elder Acres: Log Cabin w/ Indoor Pool
Living area
Exterior
Dining
Games room
Exceptional
(11 reviews)

Fully renovated lake front home on Delavan’s North Shore

Delavan

8% off
AU$9,253
for 7 nights, 1 home
AU$1,322 per night
includes taxes & fees
Fully renovated lake front home on Delavan’s North Shore
This fully equipped kitchen features a large island, modern appliances, and plenty of counter space for preparing meals, snacks, and shared moments.
Relax in the main living area where a gas fireplace, Smart TV, and comfortable seating create the ideal setting for movie nights, quiet mornings, or winding down together.
Your private Lake Geneva retreat awaits. This spacious home offers room to spread out, a large driveway, and peaceful surroundings, with easy access to Lake Como just minutes away.
Gather around the dining table for family-style meals, celebrations, and long conversations in this bright and open dining space.
Exceptional
(11 reviews)

Lake Como group retreat, bar and game room

Lake Geneva

5% off
AU$4,666
for 7 nights, 1 home
AU$667 per night
includes taxes & fees
Lake Como group retreat, bar and game room
The Williams Bay municipal pier with the beach behind it, an 11-minute walk from the house.
Williams Bay Beach from above, an 11-minute walk or 2-minute drive from the house. Sand, swim piers and the public boat launch next door.
The covered front porch at dusk, string lights on. Bring a drink out to the bench and chairs and watch the village wind down.
The kitchen from the other side: counter-height table set for a meal, open shelves of glassware, and a pass-through window to the dining room.
Exceptional
(5 reviews)

Walk-to-lake family home, porch and fire table

Williams Bay

7% off
AU$5,770
for 7 nights, 1 home
AU$824 per night
includes taxes & fees
Walk-to-lake family home, porch and fire table
Property grounds
Outdoor dining
Private kitchen
Living area
Exceptional
(171 reviews)

4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

Hubertus

12% off
AU$2,864
for 7 nights, 1 home
AU$409 per night
includes taxes & fees
4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!
Property grounds
Exterior
Exterior
Private kitchen
Exceptional
(33 reviews)

Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

Wales

8% off
AU$4,808
for 7 nights, 1 home
AU$687 per night
includes taxes & fees
Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.
Family room on lower level
Fire pit in backyard
Primary bedroom with king bed and en suite bathroom- on main level
Foosball table
Exceptional
(211 reviews)

Beautiful Lake Delavan/Lake Geneva Vacation Home

Delavan

8% off
AU$2,831
for 7 nights, 1 home
AU$404 per night
includes taxes & fees
Beautiful Lake Delavan/Lake Geneva Vacation Home
Living area
Interior
Outdoor dining
Living area
Exceptional
(30 reviews)

LAKE GENEVA HOME WITH POOL 2 BLOCKS FROM LAKE-BEACH-SWIM PIER

Lake Geneva

8% off
AU$4,910
for 7 nights, 1 home
AU$701 per night
includes taxes & fees
LAKE GENEVA HOME WITH POOL 2 BLOCKS FROM LAKE-BEACH-SWIM PIER
Abbey Springs Yacht Club. Call ahead to book reservation.
Screened in porch off of living room
Open Floor plan and fully stocked kitchen.
Lakefront with walking path.
Exceptional
(46 reviews)

AMAZING LAKE GENEVA ABBEY SPRINGS HOME + HOT TUB + 2 GOLF CARTS!

Fontana

8% off
AU$5,383
for 7 nights, 1 home
AU$769 per night
includes taxes & fees
AMAZING LAKE GENEVA ABBEY SPRINGS HOME + HOT TUB + 2 GOLF CARTS!
Dining
Living area
Bar (on property)
Living area
Exceptional
(50 reviews)

Modern A-Frame Cabin + Hot Tub + Golf Cart. Amenities Galore!

Fontana

8% off
AU$3,971
for 7 nights, 1 home
AU$567 per night
includes taxes & fees
Modern A-Frame Cabin + Hot Tub + Golf Cart. Amenities Galore!
End bedroom,  Bay window, flat screen TV & electric fireplace
flat screen TV above gas fireplace. Roku remotes for all 6 Tv's
Enjoy Sunsets in  private from inside this Swim Spa
dinning room is to the right of kitchen
Exceptional
(31 reviews)

Private 3br, with SwimSpa, Gym, by Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-

Elkhorn

8% off
AU$4,651
for 7 nights, 1 home
AU$664 per night
includes taxes & fees
Private 3br, with SwimSpa, Gym, by Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why people love visiting lively Southeast Wisconsin

The area's live music and festivals are just some of the reasons to come on holiday to Southeast Wisconsin. Renowned for its zoo, lake and sporting events, this city welcomes all visitors. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Southeast Wisconsin

Are you searching for attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Southeast Wisconsin a fun spot to go on holiday. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Springs Water Park (7.1 mi / 11.4 km)
  • Milwaukee County Zoo (9.9 mi / 15.9 km)
  • Crystal Ridge (10.3 mi / 16.6 km)
  • Milwaukee Mile Speedway (10.8 mi / 17.5 km)
  • Milwaukee County Sports Complex (12.5 mi / 20.1 km)
  • Kettle Moraine Ranch (16.2 mi / 26 km)

Exploring the natural landscape of Southeast Wisconsin

Whether you're an active traveller or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Southeast Wisconsin. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Frame Park Formal Gardens (4.2 mi / 6.8 km)
  • Little Muskego Lake (4.5 mi / 7.2 km)
  • Boerner Botanical Gardens (9.1 mi / 14.7 km)
  • Pewaukee Lake Beach (9.1 mi / 14.7 km)
  • Whitnall Park (9.1 mi / 14.7 km)
  • Pewaukee Lake (9.3 mi / 15 km)

How to get to and around Southeast Wisconsin

The nearest airport is in Waukesha, WI (UES-Waukesha County), located 5.7 mi (9.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Milwaukee, WI (MKE-General Mitchell Intl.), which is 15.5 mi (24.9 km) away.

If you prefer to travel by train, Milwaukee Airport Station, Milwaukee Intermodal Station and Sturtevant Station are the main stations that serve the city. Utilise the area's public transport and catch a ride on the metro at Clybourn & Jefferson Tram Stop or Michigan & Jackson Tram Stop if you're interested in seeing more of the city.

Frequently asked questions

What is the best area to stay in Southeast Wisconsin when booking a holiday home?
Delavan is among the more popular areas to book a holiday home in Southeast Wisconsin. Looking for some top things to do and see in this destination? Don't miss Dancing Horse Theatre and Animal Gardens.
What is the most popular type of holiday home accommodation in Southeast Wisconsin?
Houses are the most popular type of holiday home in Southeast Wisconsin, according to our data. Even if you've got something bigger or smaller in mind, Stayz has properties in all shapes and sizes. Look over our options to find your perfect match.
How much does it cost to rent a holiday home in Southeast Wisconsin?
The average price for a holiday home in Southeast Wisconsin can vary depending on factors like property type, season and length of stay. Whether you're searching for a sprawling villa with room to move around or a quaint cottage for you and your other half, just enter your travel dates to discover stays with great value.
How much does it cost to rent a beach house in Southeast Wisconsin?
Prices for beach houses in Southeast Wisconsin may vary depending on the style and size of the property and when you're travelling. Simply enter your travel dates into Stayz and the number of guests to view your options and prices. From there you can use our filters to narrow down your search by nearby activities, ratings, amenities and more.
What are popular home amenities in Southeast Wisconsin?
When it comes to home amenities that people are searching for in Southeast Wisconsin, a microwave oven, a stovetop and a fridge are the most popular. With Stayz holiday homes, you'll have options to suit your taste and style, whether you're planning to get away with family, friends or even pets.
Are there large group holiday homes in Southeast Wisconsin?
With 247 holiday homes that can host 10 or more people in Southeast Wisconsin, there's no need to leave anyone off your guest list. From holidays with the extended family to events like birthday parties and weddings, Stayz will help you find a large group home that fits the occasion.
What are the top attractions for families in Southeast Wisconsin?
Keeping the kids happy during your Southeast Wisconsin holiday is a snap with these exciting family-friendly attractions:
  • Fiserv Forum
  • American Family Field
  • Mayfair Mall
Can I find two-bedroom holiday homes in Southeast Wisconsin?
You can pick from 336 two-bedroom properties in Southeast Wisconsin. Put the kids in the second room or fill it with a couple of your favourite people. There's space for whoever's lucky enough to be joining your adventure.
Are there holiday homes with WiFi in Southeast Wisconsin?
Whether you'd like to keep up with the latest headlines, send some emails or surf your social networks, there are 542 holiday homes with WiFi in Southeast Wisconsin. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.
How old do you have to be to rent a holiday home in Southeast Wisconsin?
We advise checking with the Southeast Wisconsin holiday property you're looking at on Stayz as age restrictions vary. However, it's normally 16, 18 or 21.
How long can I rent a holiday home in Southeast Wisconsin for?
The length of time you can book a holiday home in Southeast Wisconsin is up to the property. Simply enter your desired travel dates to see a list of options offering extended stays. With loads of creature comforts like air conditioning and laundries, as well as some offering discounted weekly or monthly prices, you're sure to get the perfect place to call your home away from home in Southeast Wisconsin.

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