Southeast Wisconsin holiday rentals

We found 2,440 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southeast Wisconsin

Showing deals for:13 Nov - 20 Nov

Terrace/patio
Private kitchen
Room
Living area
Exceptional
(12 reviews)

Large Private Farmhouse with Saltwater Pool

Lake Geneva

9% off
AU$14,434
for 7 nights, 1 room
AU$2,062 per night
includes taxes & fees
Large Private Farmhouse with Saltwater Pool
Exterior
Attic balcony
Private kitchen
Sitting area
Exceptional
(19 reviews)

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

Delavan

8% off
AU$11,437
for 7 nights, 1 cottage
AU$1,634 per night
includes taxes & fees
Lakefront Haven: Waterfront Oasis with Dock, Spacious Swim Pier & Pano Lake view
Dining
Living area
Living area
Pool
Exceptional
(8 reviews)

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

Oconomowoc

9% off
AU$34,756
for 7 nights, 1 home
AU$4,965 per night
includes taxes & fees
Kohl Manor Luxury Lake 8br year round retreat Pool, Cinema, Arcade on LacLaBelle
Relaxing lighting to enjoy sunsets and nighttime gatherings
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
(155 reviews)

Island view cottage on crystal clear spring fed lake.

Burlington

6% off
AU$6,935
for 7 nights, 1 home
AU$991 per night
includes taxes & fees
Island view cottage on crystal clear spring fed lake.
Dining
Property grounds
table for 10
well built and only 15 years old
Wonderful
(59 reviews)

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

Twin Lakes

8% off
AU$7,133
for 7 nights, 1 home
AU$1,019 per night
includes taxes & fees
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
16 feet of dining that can be expanded to add another 8 feet
Great spot for  your morning coffee
Living area
Beautiful Artwork throughout
Exceptional
(108 reviews)

Private Country House near Lake Geneva, Como and Williams Bay

Lake Geneva

8% off
AU$13,360
for 7 nights, 1 home
AU$1,909 per night
includes taxes & fees
Private Country House near Lake Geneva, Como and Williams Bay
Exterior
Property grounds
Dining
Living area
Exceptional
(12 reviews)

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

Pewaukee

8% off
AU$10,353
for 7 nights, 1 home
AU$1,479 per night
includes taxes & fees
Serene 4-bedroom Lake House in Pewaukee-Hot Tub!
Exterior
Exterior
Dining
Living area
Exceptional
(43 reviews)

THE ULTIMATE LAKEHOUSE

Lake Geneva

17% off
AU$12,553
for 7 nights, 1 home
AU$1,793 per night
includes taxes & fees
THE ULTIMATE LAKEHOUSE
Dining
Property grounds
Living area
Exterior
Exceptional
(78 reviews)

Enjoy Lakefront living with family!

Racine

7% off
AU$7,718
for 7 nights, 1 home
AU$1,103 per night
includes taxes & fees
Enjoy Lakefront living with family!
Games room
Exterior
Living area
Living area
Wonderful
(10 reviews)

Fully renovated lake front home on Delavan’s North Shore

Delavan

8% off
AU$9,130
for 7 nights, 1 home
AU$1,304 per night
includes taxes & fees
Fully renovated lake front home on Delavan’s North Shore
Private kitchen
Living area
Exterior
Living area
Exceptional
(6 reviews)

The Almond Joy • Modern Lakeside Retreat

Delavan

8% off
AU$5,924
for 7 nights, 1 home
AU$846 per night
includes taxes & fees
The Almond Joy • Modern Lakeside Retreat
Interior
Private kitchen
Interior
Exterior
Exceptional
(18 reviews)

Large Lakehouse with hot tub. walk to public beach in Twin Lakes WI

Twin Lakes

8% off
AU$7,168
for 7 nights, 1 home
AU$1,024 per night
includes taxes & fees
Large Lakehouse with hot tub. walk to public beach in Twin Lakes WI
Interior
Terrace/patio
Interior
Dining
Exceptional
(92 reviews)

Enjoy Beachfront Living With family!

Racine

8% off
AU$6,387
for 7 nights, 1 home
AU$912 per night
includes taxes & fees
Enjoy Beachfront Living With family!
Living area
Terrace/patio
Private kitchen
Room
Exceptional
(7 reviews)

Brady St Retreat! 4BR House w Patio & Fenced Yard

Milwaukee

6% off
AU$2,931
for 7 nights, 1 home
AU$419 per night
includes taxes & fees
Brady St Retreat! 4BR House w Patio & Fenced Yard
Private kitchen
Lobby
Exterior
Pool
Exceptional
(11 reviews)

South Elder Acres: Log Cabin w/ Indoor Pool

Lake Geneva

8% off
AU$14,404
for 7 nights, 1 home
AU$2,058 per night
includes taxes & fees
South Elder Acres: Log Cabin w/ Indoor Pool
Enjoy sitting under the covered wrap around porch with your favorite beverage.
Family / TV Room
Watch people stroll down the main street from the Main Level Living Room
Coffee station with drip coffee maker and Keurig.  Includes coffee and K-cups.
Exceptional
(162 reviews)

Our Happy Place in Cedarburg, WI

Cedarburg

8% off
AU$2,432
for 7 nights, 1 home
AU$347 per night
includes taxes & fees
Our Happy Place in Cedarburg, WI
Landing looking down from 2nd floor
Massive living room with Roku-enabled TV, wi-fi, comfy furniture, cozy woodwork
Dining room with beautiful woodwork and antique upright piano
Front porch for relaxing or people watching
Exceptional
(8 reviews)

Huge Historic House Centrally Located in Milwaukee

Milwaukee

8% off
AU$3,814
for 7 nights, 1 home
AU$545 per night
includes taxes & fees
Huge Historic House Centrally Located in Milwaukee
Room
Outdoor dining
Interior
Exterior detail
Exceptional
(9 reviews)

Gorgeous space with huge porch.

Milwaukee

7% off
AU$2,252
for 7 nights, 1 home
AU$322 per night
includes taxes & fees
Gorgeous space with huge porch.
Side yard
Harbor and Yacht Club with downtown Racine in the background.
Terrace/patio
Native garden
Exceptional
(47 reviews)

Cozy, historic Cream City brick, "Workers Cottage" 2 blocks from Lake Michigan.

Racine

15% off
AU$1,780
for 7 nights, 1 home
AU$254 per night
includes taxes & fees
Cozy, historic Cream City brick, "Workers Cottage" 2 blocks from Lake Michigan.
Private kitchen
Private kitchen
Property grounds
Living area
Wonderful
(6 reviews)

Quiet Retreat in Morgan Heights, Sleeps 6, 1.5 baths

Milwaukee

17% off
AU$2,037
for 7 nights, 1 home
AU$291 per night
includes taxes & fees
Quiet Retreat in Morgan Heights, Sleeps 6, 1.5 baths
Property grounds
Terrace/patio
Interior
Living area
Exceptional
(21 reviews)

Scenic Waterfront Lake Michigan Escape

Racine

7% off
AU$4,348
for 7 nights, 1 home
AU$621 per night
includes taxes & fees
Scenic Waterfront Lake Michigan Escape
Interior
Property grounds
Exterior
Living area
Exceptional
(41 reviews)

Cozy Cottage by the Lake! Kayaks! BIG Deck w/ Great Lake Views! Golf Cart Rental

Salem

12% off
AU$1,827
for 7 nights, 1 home
AU$261 per night
includes taxes & fees
Cozy Cottage by the Lake! Kayaks! BIG Deck w/ Great Lake Views! Golf Cart Rental
Living area
Living area
Exterior
Room
Exceptional
(16 reviews)

Lake Geneva Haven - Located in the Center of Everything!

Lake Geneva

7% off
AU$3,238
for 7 nights, 1 home
AU$463 per night
includes taxes & fees
Lake Geneva Haven - Located in the Center of Everything!
Private kitchen
Living area
House has a large fenced in yard in the back. Check out the video.
Dining
Very good
(39 reviews)

“Walk to Geneva Lake! 3BR/2BA Family Home w/ Deck & Fenced Yard for Pets”

Williams Bay

8% off
AU$4,634
for 7 nights, 1 home
AU$662 per night
includes taxes & fees
“Walk to Geneva Lake! 3BR/2BA Family Home w/ Deck & Fenced Yard for Pets”
  • 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. Take in top local attractions such as Lake Michigan and American Family Field. 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)
  • Milwaukee Mile Speedway (10.8 mi / 17.5 km)
  • Milwaukee County Sport Complex (12.5 mi / 20.1 km)
  • Green Meadows Petting Farm (13.4 mi / 21.6 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:

  • Fox River Park (3.2 mi / 5.2 km)
  • 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)
  • 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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