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

Search Vacation 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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Southeast Wisconsin holiday homes

A modern kitchen with a large island, stainless steel sink, and pendant lights.

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, (41 reviews)
"Great place and very clean"
United States
Jason d.
The price is HK$1,307
HK$2,869 total
includes taxes & fees
20 Oct - 21 Oct
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
A dining area with a table set for two, a coffee maker, and a window with blinds.

2. 1BR Pro Flat + Office; near Hospitals. Garage + Yard

1BR Pro Flat + Office; near Hospitals. Garage + Yard
Fair Park
The price is HK$1,036
HK$2,970 total
includes taxes & fees
8 Nov - 9 Nov
1BR Pro Flat + Office; near Hospitals. Garage + Yard
A bedroom with a bed, a desk, a chair, a lamp, a ceiling fan, and a window with a sign.

3. The Nohl | A Lake Effect Stay Near Brady Street

The Nohl | A Lake Effect Stay Near Brady Street
Lower East Side
The price is HK$659
HK$2,047 total
includes taxes & fees
20 Oct - 21 Oct
The Nohl | A Lake Effect Stay Near Brady Street
A metal-framed table with a wooden top, mesh storage compartments, and a vase with flowers.

4. 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 HK$950
HK$2,008 total
includes taxes & fees
20 Oct - 21 Oct
Quiet Bay View Getaway
A hot tub under a covered area with a wooden roof, surrounded by a white fence, trees, and a clear sky.

5. 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 HK$1,402
HK$2,657 total
includes taxes & fees
20 Oct - 21 Oct
Private Hot Tub • Bright Home Near Downtown
A dining area with a round table, four chairs, a wooden floor, a door, and a lamp.

6. 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 HK$530
HK$1,670 total
includes taxes & fees
26 Oct - 27 Oct
Quiet House
A room with a wooden floor, a television on a stand, a white door, and a window with a view of buildings outside.

7. Best location in Milwaukee! Upper Duplex Unit

Best location in Milwaukee! Upper Duplex Unit
Downtown Milwaukee
8.6 out of 10, Excellent, (25 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 HK$578
HK$1,322 total
includes taxes & fees
20 Oct - 21 Oct
Best location in Milwaukee! Upper Duplex Unit
A modern living room with a sofa, a coffee table, and a television mounted on the wall.

8. Near Lake Michigan • Coffee Bar • Workspace

Near Lake Michigan • Coffee Bar • Workspace
Milwaukee
The price is HK$546
HK$4,049 total
includes taxes & fees
20 Oct - 21 Oct
Near Lake Michigan • Coffee Bar • Workspace
A modern kitchen with stainless steel appliances, white cabinets, and a wooden floor.

9. 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, (19 reviews)
"Very nice,clean, very satisfied"
United States
dawn h.
The price is HK$677
HK$2,038 total
includes taxes & fees
20 Oct - 21 Oct
Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6
A house with a front porch, steps, and a small garden area.

10. 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 HK$439
HK$784 total
includes taxes & fees
13 Nov - 14 Nov
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
A single-story house with a green exterior, a front porch, and a garage.

11. King Bed • Vintage Urban Oasis • Near MKE Airport

King Bed • Vintage Urban Oasis • Near MKE Airport
Town of Lake
10.0 out of 10, Exceptional, (2 reviews)
"Small place perfect for a solo traveler or a small family. Cute mix of old and new furnishings and decor. Updated fixtures and appliances. Had everything needed in the kitchen space to grocery shop and eat it. I was traveling for work and needed a home away from home without much fuss and this place checked at the boxes.."
United States
Rachel C.
The price is HK$1,093
HK$2,122 total
includes taxes & fees
21 Oct - 22 Oct
King Bed • Vintage Urban Oasis • Near MKE Airport
A living room with a leather sofa, a round coffee table, and a dining area with a table and chairs.

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 HK$1,391
HK$2,695 total
includes taxes & fees
22 Oct - 23 Oct
Historic home - walk to village center. Original features with modern updates.
A two-story house with a balcony, a front porch, and a visible garage.

13. Sytlish Retreat Near Wedding Venues & Downtown

Sytlish Retreat Near Wedding Venues & Downtown
Oconomowoc
10.0 out of 10, Exceptional, (30 reviews)
"Nicely remodeled home that was perfect for our trip to Oconomowoc"
United States
Carl G.
The price is HK$1,906
HK$4,540 total
includes taxes & fees
20 Oct - 21 Oct
Sytlish Retreat Near Wedding Venues & Downtown
A beach with a wooden bench, a dock, and calm water.

14. 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, (15 reviews)
"Nice comfy home. Very relaxing"
United States
linda b.
The price is HK$1,413
HK$2,832 total
includes taxes & fees
8 Nov - 9 Nov
Deck + Fire Pit, Walk to Browns Lake Private Beach, Game Room, Near Lake Geneva
A modern kitchen with white cabinets, a stainless steel stove, and a wooden countertop.

15. Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!
Downtown Milwaukee
10.0 out of 10, Exceptional, (12 reviews)
"Nice place, close to Brady Street."
United States
Kevin M.
The price is HK$487
HK$2,239 total
includes taxes & fees
28 Oct - 29 Oct
Remodeled Home - Steps from Brady Street!
A spacious hallway with wooden flooring, a central dining table with chairs, a chandelier, and a bookshelf with books.

16. Three Bedroom Upper

Three Bedroom Upper
Riverwest
9.6 out of 10, Exceptional, (107 reviews)
"Close to everything in Milwaukee"
United States
Terri E.
The price is HK$1,377
HK$1,846 total
includes taxes & fees
22 Oct - 23 Oct
Three Bedroom Upper
A room with a ping pong table, a washing machine, and a bicycle.

17. A Quiet Escape Minutes From Downtown Milwaukee 3 Bedroom Duplex

A Quiet Escape Minutes From Downtown Milwaukee 3 Bedroom Duplex
3.0 star property
Milwaukee
The price is HK$2,886
HK$5,651 total
includes taxes & fees
20 Oct - 21 Oct
A Quiet Escape Minutes From Downtown Milwaukee 3 Bedroom Duplex
A bedroom with two beds, a window with curtains, a wall-mounted shelf with decorative items, and a ceiling light fixture.

18. EKO Stay - Your Home Away From Home

EKO Stay - Your Home Away From Home
Wauwatosa
10.0 out of 10, Exceptional, (2 reviews)
"The location was perfect. The unit is clean and nicely updated. The pictures are a good representation. The hosts were great and very open to helping and answering questions (even if it was the same question again). It's ideal for a small family and sleeps the number posted in the listing. Would definitely stay again!"
United States
sussan s.
The price is HK$2,093
HK$4,591 total
includes taxes & fees
1 Nov - 2 Nov
EKO Stay - Your Home Away From Home
Interior

19. 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 HK$816
HK$2,526 total
includes taxes & fees
2 Nov - 3 Nov
The Pink Lady - Stylish Walker’s Point Home
Outdoor seating with wicker chairs and red umbrellas, a 'DO NOT ENTER' sign, and a building with 'noodles & company' signage.

20. 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, (49 reviews)
"Nice quite spot close to highway"
United States
Dan K.
The price is HK$1,530
HK$3,017 total
includes taxes & fees
27 Oct - 28 Oct
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southeast Wisconsin Hotel Reviews

Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

10/10 Excellent
"I like that its a family-friendly hotel, the room we got is clean and spacious. Very “condo style” setup! Lots of amenities to enjoy for the whole family. The indoor waterpark is awesome! My kid loved it especially the lazy river. Will definitely come back and recommend to friends!"
Shirley 1-night trip
Posted 2 hours ago
Timber Ridge Lodge and Waterpark

Find out more about Southeast Wisconsin

Southeast Wisconsin Vacation Homes information

Number of reviews
436
Accommodation
810 Vacation Homes
Lowest Price
HK$784
Highest Price
HK$5,651

Explore a world of travel with Expedia