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

Southeast Wisconsin Vacation Rentals

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Check prices for these dates

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

Our top choices for Southeast Wisconsin vacation 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 CA $264
CA $559 total
includes taxes & fees
Oct 19 - Oct 20
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 CA $188
CA $538 total
includes taxes & fees
Nov 8 - Nov 9
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 CA $120
CA $372 total
includes taxes & fees
Oct 12 - Oct 13
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.

4. 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 CA $96
CA $302 total
includes taxes & fees
Oct 12 - Oct 13
Quiet House
A fire pit surrounded by wooden Adirondack chairs on a paved patio, with string lights and a wooden fence in a wooded backyard.

5. 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 CA $225
CA $676 total
includes taxes & fees
Oct 14 - Oct 15
The Eucalyptus — A 4 bedroom Retreat
A hot tub under a covered area with a wooden roof, surrounded by a white fence, trees, and a clear sky.

6. 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 CA $255
CA $486 total
includes taxes & fees
Oct 14 - Oct 15
Private Hot Tub • Bright Home Near Downtown
A beach with a view of the water, boats, and a distant shoreline.

7. 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 CA $458
CA $717 total
includes taxes & fees
Oct 17 - Oct 18
Spa House by the beach. Pewaukee Lake
A house with a front porch, steps, and a small garden area.

8. 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 CA $71
CA $133 total
includes taxes & fees
Nov 11 - Nov 12
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
A living room with a leather sofa, a round coffee table, and a dining area with a table and chairs.

9. 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 CA $253
CA $493 total
includes taxes & fees
Oct 13 - Oct 14
Historic home - walk to village center. Original features with modern updates.
A room with a wooden floor, a television on a stand, a white door, and a window with a view of buildings outside.

10. 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 CA $105
CA $240 total
includes taxes & fees
Oct 12 - Oct 13
Best location in Milwaukee! Upper Duplex Unit
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
"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 CA $199
CA $387 total
includes taxes & fees
Oct 12 - Oct 13
King Bed • Vintage Urban Oasis • Near MKE Airport
A two-story house with a balcony, a front porch, and a visible garage.

12. 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 CA $403
CA $901 total
includes taxes & fees
Oct 13 - Oct 14
Sytlish Retreat Near Wedding Venues & Downtown
A modern living room with a sofa, a coffee table, and a television mounted on the wall.

13. Near Lake Michigan • Coffee Bar • Workspace

Near Lake Michigan • Coffee Bar • Workspace
Milwaukee
The price is CA $118
CA $760 total
includes taxes & fees
Oct 19 - Oct 20
Near Lake Michigan • Coffee Bar • Workspace
A patio with outdoor furniture, a grill, and a satellite dish on a two-story building.

14. 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 CA $524
CA $1,061 total
includes taxes & fees
Oct 25 - Oct 26
A Quiet Escape Minutes From Downtown Milwaukee 3 Bedroom Duplex
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)
"Great stay and great communication throughout. Would stay again, thank you!"
United States
David M.
The price is CA $98
CA $417 total
includes taxes & fees
Oct 19 - Oct 20
Remodeled Home - Steps from Brady Street!
A bedroom with two beds, a window with curtains, a wall-mounted shelf with decorative items, and a ceiling light fixture.

16. 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 CA $380
CA $826 total
includes taxes & fees
Oct 18 - Oct 19
EKO Stay - Your Home Away From Home
A modern kitchen with stainless steel appliances, white cabinets, and a wooden floor.

17. 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 CA $117
CA $361 total
includes taxes & fees
Oct 26 - Oct 27
Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6
A beach with a wooden bench, a dock, and calm water.

18. 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 CA $250
CA $469 total
includes taxes & fees
Nov 4 - Nov 5
Deck + Fire Pit, Walk to Browns Lake Private Beach, Game Room, Near Lake Geneva
A spacious hallway with wooden flooring, a central dining table with chairs, a chandelier, and a bookshelf with books.

19. 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 CA $250
CA $337 total
includes taxes & fees
Oct 12 - Oct 13
Three Bedroom Upper
A beach with people walking and swimming, a lifeguard tower, and a clear sky.

20. 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 CA $160
CA $479 total
includes taxes & fees
Oct 12 - Oct 13
2bed 1.5bath House, Lower Eastside, King Bed, 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.
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Top Southeast Wisconsin Hotel Reviews

The Iron Horse Hotel

The Iron Horse Hotel

10/10 Excellent
"I had to check in early due to an upcoming event and the front desk staff person couldn’t have been more helpful. The room was perfect and fit the vibe of the hotel. The staff at the bar outside were attentive. I’ll definitely be back!"
Catherine 1-night trip
Posted less than an hour ago
The Iron Horse Hotel

Find out more about Southeast Wisconsin

Southeast Wisconsin Vacation Homes information

Number of reviews
356
Accommodation
838 Vacation Homes
Lowest Price
CA $133
Highest Price
CA $1,061

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