A modern architectural building with a unique design, featuring a prominent tower and curved structures.

Holiday Homes in Southeast Wisconsin

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Southeast Wisconsin holiday homes

1. Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
Waukesha
9.8 out of 10, Exceptional, (45 reviews)
"Great place and very clean"
United States
Jason d.
The price is NZ$641
includes taxes & fees
11 Nov - 12 Nov
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

2. New: Tremendous 4-bedroom house on private lot in charming Brookfield

New: Tremendous 4-bedroom house on private lot in charming Brookfield
Brookfield
10.0 out of 10, Exceptional, (1 review)
"Loved our stay in Brookfield, WI.Tonga was very helpful and responded quickly whenever I messaged.This was the perfect house for our family for the weekend. Quiet, nice neighborhood close to shopping and places to eat. Beautiful spacious backyard for the kids to play and a great place for a fire at night. All the rooms were spacious and we had everything we needed in the kitchen. Would highly recommend for anyone looking for a relaxing vacation home."
United States
Lauren E.
The price is NZ$849
includes taxes & fees
23 Nov - 24 Nov
New: Tremendous 4-bedroom house on private lot in charming Brookfield

3. Be Relax House, Cozy 2BR Milwaukee Getaway, Sleeps 4

Be Relax House, Cozy 2BR Milwaukee Getaway, Sleeps 4
Milwaukee
The price is NZ$408
includes taxes & fees
7 Dec - 8 Dec
Be Relax House, Cozy 2BR Milwaukee Getaway, Sleeps 4

4. Workspace • Coffee Bar • Modern 4BR • Sleeps 10

Workspace • Coffee Bar • Modern 4BR • Sleeps 10
Milwaukee
The price is NZ$858
includes taxes & fees
10 Nov - 11 Nov
Workspace • Coffee Bar • Modern 4BR • Sleeps 10

5. Quiet Bay View Getaway

Quiet Bay View Getaway
Town of Lake
8.0 out of 10, Very good, (1 review)
"Having to navigate the stairs to the basement at our age was a little difficult and could use a kitchen sink but other than that it was fine."
United States
Carl B.
The price is NZ$433
includes taxes & fees
22 Nov - 23 Nov
Quiet Bay View Getaway

6. Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Kenosha
9.4 out of 10, Exceptional, (96 reviews)
"Comfy, cozy, and clean place to stay!!"
United States
Erin
The price is NZ$158
includes taxes & fees
11 Nov - 12 Nov
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

7. Quiet House

Quiet House
Milwaukee
7.6 out of 10, Good, (22 reviews)
"The house was clean, the neighborhood was quiet. The house was very close to the Baird center and other places we wanted to visit."
United States
Steven
The price is NZ$361
includes taxes & fees
10 Nov - 11 Nov
Quiet House

8. Private Hot Tub • Bright Home Near Downtown

Private Hot Tub • Bright Home Near Downtown
Oconomowoc
10.0 out of 10, Exceptional, (6 reviews)
"Our stay was wonderful. Our host was very responsive to questions, and the home was welcoming and had all needed amenities. "
United States
Heather F.
The price is NZ$595
includes taxes & fees
15 Nov - 16 Nov
Private Hot Tub • Bright Home Near Downtown

9. NEW! Comfortable 9-bedroom house near local attractions, handicap accessible

NEW! Comfortable 9-bedroom house near local attractions, handicap accessible
West Allis
The price is NZ$927
includes taxes & fees
11 Nov - 12 Nov
NEW! Comfortable 9-bedroom house near local attractions, handicap accessible

10. House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Johnson Woods
9.6 out of 10, Exceptional, (52 reviews)
"Nice quite spot close to highway"
United States
Dan K.
The price is NZ$627
includes taxes & fees
16 Nov - 17 Nov
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

11. Deck + Fire Pit, Walk to Browns Lake Private Beach, Game Room, Near Lake Geneva

Deck + Fire Pit, Walk to Browns Lake Private Beach, Game Room, Near Lake Geneva
Burlington
9.8 out of 10, Exceptional, (16 reviews)
"Nice comfy home. Very relaxing"
United States
linda b.
The price is NZ$533
includes taxes & fees
2 Dec - 3 Dec
Deck + Fire Pit, Walk to Browns Lake Private Beach, Game Room, Near Lake Geneva

12. Historic home - walk to village center. Original features with modern updates.

Historic home - walk to village center. Original features with modern updates.
Greendale
9.8 out of 10, Exceptional, (56 reviews)
"Stayed here many times. Great as always."
United States
Kristi T.
The price is NZ$586
includes taxes & fees
11 Nov - 12 Nov
Historic home - walk to village center. Original features with modern updates.

13. 2bed 1.5bath House, Lower Eastside, King Bed, Fire Pit, Sleeps 6

2bed 1.5bath House, Lower Eastside, King Bed, Fire Pit, Sleeps 6
Downtown Milwaukee
10.0 out of 10, Exceptional, (1 review)
"Overall had the best stay with me and my 3 kids! The house was even better than the pictures. Cute decor, comfy beds, great kitchen amenities to make your stay feel right at home. The host provided clear, easy house and parking instructions! And a grocery store is a close, 5 minute for easy shopping trips. "
United States
Kristen M.
The price is NZ$451
includes taxes & fees
11 Nov - 12 Nov
2bed 1.5bath House, Lower Eastside, King Bed, Fire Pit, Sleeps 6

14. New Spacious 8-bedroom house on large private lot close to Milwaukee attractions

New Spacious 8-bedroom house on large private lot close to Milwaukee attractions
Milwaukee
10.0 out of 10, Exceptional, (1 review)
"This property was perfect for our needs!"
United States
Amanda D.
The price is NZ$905
includes taxes & fees
7 Dec - 8 Dec
New Spacious 8-bedroom house on large private lot close to Milwaukee attractions

15. Best location in Milwaukee! Upper Duplex Unit

Best location in Milwaukee! Upper Duplex Unit
Downtown Milwaukee
8.4 out of 10, Very good, (26 reviews)
"This property couldn’t be better situated for a great stay. The surrounding neighborhood is vibrant and lively but the home is just enough off the beaten path that you have a quiet spot to enjoy. Would absolutely return. Great host."
United States
Aaron W.
The price is NZ$287
includes taxes & fees
10 Nov - 11 Nov
Best location in Milwaukee! Upper Duplex Unit

16. Rustic Charm: Pewaukee Lake Cabin, Sauna & Hot Tub

Rustic Charm: Pewaukee Lake Cabin, Sauna & Hot Tub
Pewaukee
10.0 out of 10, Exceptional, (30 reviews)
"Wonderful place to stay nice and peaceful"
United States
Danny H.
The price is NZ$2,302
includes taxes & fees
15 Nov - 16 Nov
Rustic Charm: Pewaukee Lake Cabin, Sauna & Hot Tub

17. Workspace • Fireplace • Coffee Bar • Sleeps 12

Workspace • Fireplace • Coffee Bar • Sleeps 12
Milwaukee
6.0 out of 10, (2 reviews)
"The house was nice and accommodated our travel greatly. Communication before and during the stay from the host, was spot on. Everything went smoothly."
United States
Chris B.
The price is NZ$875
includes taxes & fees
16 Nov - 17 Nov
Workspace • Fireplace • Coffee Bar • Sleeps 12

18. The Pink Lady - Stylish Walker’s Point Home

The Pink Lady - Stylish Walker’s Point Home
Fifth Ward
9.6 out of 10, Exceptional, (9 reviews)
"Great time. Fun place to stay"
United States
syed a.
The price is NZ$523
includes taxes & fees
10 Nov - 11 Nov
The Pink Lady - Stylish Walker’s Point Home

19. Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!
Downtown Milwaukee
10.0 out of 10, Exceptional, (13 reviews)
"Nice place, close to Brady Street."
United States
Kevin M.
The price is NZ$510
includes taxes & fees
16 Nov - 17 Nov
Remodeled Home - Steps from Brady Street!

20. Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6

Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6
Lake Geneva
9.0 out of 10, Wonderful, (20 reviews)
"Very nice,clean, very satisfied"
United States
dawn h.
The price is NZ$450
includes taxes & fees
15 Nov - 16 Nov
Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Southeast Wisconsin Hotel Reviews

Find out more about Southeast Wisconsin

Southeast Wisconsin Holiday Homes information

Number of reviews
374
Accommodation
771 Holiday Homes
Lowest Price
NZ$158
Highest Price
NZ$2,302

Explore a world of travel with Expedia