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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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, (43 reviews)
"Great place and very clean"
United States
Jason d.
The price is CA $233
CA $528 total
includes taxes & fees
Nov 3 - Nov 4
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 $184
CA $529 total
includes taxes & fees
Nov 10 - Nov 11
1BR Pro Flat + Office; near Hospitals. Garage + Yard
A bedroom with a bed, a dresser, a nightstand, a lamp, and a television on a dresser.

3. 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 CA $337
CA $838 total
includes taxes & fees
Dec 1 - Dec 2
NEW! Comfortable 9-bedroom house near local attractions, handicap accessible
A living room with a large brown sofa, a dining area with wooden chairs, and a kitchen area with a refrigerator and microwave.

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

Be Relax House, Cozy 2BR Milwaukee Getaway, Sleeps 4
Milwaukee
The price is CA $175
CA $310 total
includes taxes & fees
Nov 17 - Nov 18
Be Relax House, Cozy 2BR Milwaukee Getaway, Sleeps 4
A modern kitchen with stainless steel appliances, a granite countertop, and a large window.

5. 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 CA $260
CA $700 total
includes taxes & fees
Nov 23 - Nov 24
New: Tremendous 4-bedroom house on private lot in charming Brookfield
A modern bathroom with a white vanity, a mirror, and a blue rug.

6. 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 CA $169
CA $351 total
includes taxes & fees
Dec 1 - Dec 2
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.

7. 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 $277
CA $506 total
includes taxes & fees
Nov 1 - Nov 2
Private Hot Tub • Bright Home Near Downtown
A dining area with a round table, four chairs, a wooden floor, a door, and a lamp.

8. 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 $94
CA $296 total
includes taxes & fees
Nov 10 - Nov 11
Quiet House
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 $248
CA $480 total
includes taxes & fees
Nov 3 - Nov 4
Historic home - walk to village center. Original features with modern updates.
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 CA $70
CA $130 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
A modern living room with a sectional sofa, a coffee table, and a black furry rug.

11. Near Lake Michigan • Coffee Bar • Workspace

Near Lake Michigan • Coffee Bar • Workspace
Milwaukee
The price is CA $110
CA $742 total
includes taxes & fees
Nov 2 - Nov 3
Near Lake Michigan • Coffee Bar • Workspace
A bedroom with bunk beds, a dresser, a lamp, and a framed picture on the wall.

12. Three Bedroom Upper

Three Bedroom Upper
Riverwest
9.6 out of 10, Exceptional, (110 reviews)
"Everything was great. Location was very good. Highly recommend!!"
United States
Michelle J.
The price is CA $195
CA $263 total
includes taxes & fees
Nov 1 - Nov 2
Three Bedroom Upper
A residential backyard with a fire pit, outdoor seating, and string lights.

13. Sytlish Retreat Near Wedding Venues & Downtown

Sytlish Retreat Near Wedding Venues & Downtown
Oconomowoc
10.0 out of 10, Exceptional, (31 reviews)
"Nicely remodeled home that was perfect for our trip to Oconomowoc"
United States
Carl G.
Sytlish Retreat Near Wedding Venues & Downtown
A modern kitchen with white cabinets, a stainless steel stove, and a wooden countertop.

14. 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 CA $77
CA $366 total
includes taxes & fees
Nov 3 - Nov 4
Remodeled Home - Steps from Brady Street!
A snow-covered outdoor area with a central fire pit surrounded by wooden stools, string lights overhead, and a building in the background.

15. 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 CA $214
CA $457 total
includes taxes & fees
Dec 1 - Dec 2
Deck + Fire Pit, Walk to Browns Lake Private Beach, Game Room, Near Lake Geneva
A compact kitchen with white cabinets, a built-in microwave, a gas stove, and a granite countertop.

16. 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 CA $204
CA $369 total
includes taxes & fees
Nov 3 - Nov 4
King Bed • Vintage Urban Oasis • Near MKE Airport
Two teal armchairs with white cushions and a vase of colorful flowers on a white table.

17. 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 $139
CA $444 total
includes taxes & fees
Nov 2 - Nov 3
2bed 1.5bath House, Lower Eastside, King Bed, Fire Pit, Sleeps 6
A room with a wooden floor, a television on a stand, a white door, and a window with a view of buildings outside.

18. 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 CA $103
CA $222 total
includes taxes & fees
Nov 1 - Nov 2
Best location in Milwaukee! Upper Duplex Unit
A house with a porch, a covered entryway, and a small front yard.

19. 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, (51 reviews)
"Nice quite spot close to highway"
United States
Dan K.
The price is CA $272
CA $486 total
includes taxes & fees
Nov 19 - Nov 20
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
A spacious interior with a stone staircase, a large window, and a cozy seating area.

20. Eclectic Hubertus Home w/ Game Room & Fire Pit!

Eclectic Hubertus Home w/ Game Room & Fire Pit!
Hubertus
9.8 out of 10, Exceptional, (28 reviews)
"The house was fun and amazing! Our family loved the sprawling layout and the hip retro vibe! Excellent value for the price! Wish we could have stayed longer! Would highly recommend!"
United States
Humphries D.
The price is CA $383
CA $1,047 total
includes taxes & fees
Nov 29 - Nov 30
Eclectic Hubertus Home w/ Game Room & Fire Pit!
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

Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

8/10 Good
"Nice hotel, friendly staff. Only negative is that while housekeeping came to drop off more bottles of water that we would be charged for if opening, The didn't bother to even remake our bed. I didn't expect new linens, but I would at minimum expect the bed remade of they intruded into my room."
HEATHER 2-night trip
Posted 12 hours ago
Hyatt Regency Milwaukee

Find out more about Southeast Wisconsin

Southeast Wisconsin Vacation Homes information

Number of reviews
354
Accommodation
810 Vacation Homes
Lowest Price
CA $130
Highest Price
CA $1,047

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