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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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, (40 reviews)
"Great place and very clean"
United States
Jason d.
The price is HK$1,452
HK$3,051 total
includes taxes & fees
19 Oct - 20 Oct
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
A modern kitchen with dark cabinets, a white stove, and a dining area with a table and chairs.

2. Upper Pro Retreat near Hospitals - 30 day min - Garage & Yard. Dog-friendly!

Upper Pro Retreat near Hospitals - 30 day min - Garage & Yard. Dog-friendly!
Fair Park
10.0 out of 10, Exceptional, (3 reviews)
"I chose this area to visit family, once again, Lorinda was the best! I will visit again soon. "
United States
AnnaLisa S.
Upper Pro Retreat near Hospitals - 30 day min - Garage & Yard. Dog-friendly!
A fire pit surrounded by wooden Adirondack chairs on a paved patio, with string lights and a wooden fence in a wooded backyard.

3. The Eucalyptus — A 4 bedroom Retreat

The Eucalyptus — A 4 bedroom Retreat
Cannon Park
10.0 out of 10, Exceptional, (7 reviews)
"Great location, very clean."
United States
James M.
The price is HK$1,236
HK$3,594 total
includes taxes & fees
14 Oct - 15 Oct
The Eucalyptus — A 4 bedroom Retreat
A beach with a view of the water, boats, and a distant shoreline.

4. Spa House by the beach. Pewaukee Lake

Spa House by the beach. Pewaukee Lake
Downtown Pewaukee
9.0 out of 10, Wonderful, (2 reviews)
"Lovely relaxing home. Had a great time. Train traffic can be a bit much especially if you’re a lite sleeper. Overall great experience."
United States
Ryan E.
The price is HK$2,519
HK$3,914 total
includes taxes & fees
17 Oct - 18 Oct
Spa House by the beach. Pewaukee Lake
A bedroom with a bed, a desk, a chair, a lamp, a ceiling fan, and a window with a sign.

5. 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
12 Oct - 13 Oct
The Nohl | A Lake Effect Stay Near Brady Street
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$1,661 total
includes taxes & fees
12 Oct - 13 Oct
Quiet House
A living room with a leather sofa, a round coffee table, and a dining area with a table and chairs.

7. 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
12 Oct - 13 Oct
Historic home - walk to village center. Original features with modern updates.
A metal-framed table with a wooden top, mesh storage compartments, and a vase with flowers.

8. 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$1,804 total
includes taxes & fees
12 Oct - 13 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.

9. 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
13 Oct - 14 Oct
Private Hot Tub • Bright Home Near Downtown
A beach with a wooden bench, a dock, and calm water.

10. 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
9.2 out of 10, Wonderful, (15 reviews)
"Nice comfy home. Very relaxing"
United States
linda b.
The price is HK$1,373
HK$2,591 total
includes taxes & fees
4 Nov - 5 Nov
Deck + Fire Pit, Walk to Browns Lake Private Beach, Game Room, Near Lake Geneva
A modern living room with a sofa, a coffee table, and a television mounted on the wall.

11. Near Lake Michigan • Coffee Bar • Workspace

Near Lake Michigan • Coffee Bar • Workspace
Milwaukee
The price is HK$649
HK$4,185 total
includes taxes & fees
19 Oct - 20 Oct
Near Lake Michigan • Coffee Bar • Workspace
A single-story house with a green exterior, a front porch, and a garage.

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

King Bed • Vintage Urban Oasis • Near MKE Airport
Town of Lake
"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
12 Oct - 13 Oct
King Bed • Vintage Urban Oasis • Near MKE Airport
A spacious hallway with wooden flooring, a central dining table with chairs, a chandelier, and a bookshelf with books.

13. Three Bedroom Upper

Three Bedroom Upper
Riverwest
9.6 out of 10, Exceptional, (105 reviews)
"Close to everything in Milwaukee"
United States
Terri E.
The price is HK$1,377
HK$1,846 total
includes taxes & fees
12 Oct - 13 Oct
Three Bedroom Upper
A modern kitchen with stainless steel appliances, white cabinets, and a wooden floor.

14. 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)
"Super clean,quiet house! Close to water for us to launch our boat. We would definitely stay again, Thank You"
United States
kelly b.
The price is HK$642
HK$1,989 total
includes taxes & fees
25 Oct - 26 Oct
Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6
A patio with outdoor furniture, a grill, and a satellite dish on a two-story building.

15. 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$5,736 total
includes taxes & fees
25 Oct - 26 Oct
A Quiet Escape Minutes From Downtown Milwaukee 3 Bedroom Duplex
A two-story house with a balcony, a front porch, and a visible garage.

16. 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$2,217
HK$4,926 total
includes taxes & fees
13 Oct - 14 Oct
Sytlish Retreat Near Wedding Venues & Downtown
A room with a wooden floor, a television on a stand, a white door, and a window with a view of buildings outside.

17. Best location in Milwaukee! Upper Duplex Unit

Best location in Milwaukee! Upper Duplex Unit
Downtown Milwaukee
8.6 out of 10, Excellent, (24 reviews)
"Overall good stay in a charming Milwaukee duplex. Primary bedroom could use some blackout curtains. Shower/tub is a little small."
United States
Laura R.
The price is HK$578
HK$1,322 total
includes taxes & fees
12 Oct - 13 Oct
Best location in Milwaukee! Upper Duplex Unit
Outdoor seating with wicker chairs and red umbrellas, a 'DO NOT ENTER' sign, and a building with 'noodles & company' signage.

18. 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$2,998 total
includes taxes & fees
20 Oct - 21 Oct
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
A beach with people walking and swimming, a lifeguard tower, and a clear sky.

19. 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 HK$879
HK$2,618 total
includes taxes & fees
12 Oct - 13 Oct
2bed 1.5bath House, Lower Eastside, King Bed, Fire Pit, Sleeps 6
A modern kitchen with light wood cabinets, a stainless steel refrigerator, a stove, and a marble countertop.

20. 3-bedroom bungalow with WiFi vibrant Milwaukee

3-bedroom bungalow with WiFi vibrant Milwaukee
Milwaukee
9.6 out of 10, Exceptional, (15 reviews)
"Perfect location, clean, easy access and very responsive."
United States
Anonymous traveller
The price is HK$1,287
HK$3,562 total
includes taxes & fees
12 Oct - 13 Oct
3-bedroom bungalow with WiFi vibrant Milwaukee
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

Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

10/10 Excellent
"The rooms need to microwave other than that everything was great"
Christine 1-night trip
Posted 1 hour ago
Sheraton Milwaukee Brookfield Hotel

Find out more about Southeast Wisconsin

Southeast Wisconsin Vacation Homes information

Number of reviews
314
Accommodation
810 Vacation Homes
Lowest Price
HK$1,322
Highest Price
HK$5,736

Explore a world of travel with Expedia