Search Vacation Homes in Southeast Wisconsin

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In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Southeast Wisconsin vacation homes

Property grounds
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Vacation Home in Kenosha

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
9.6 out of 10, Exceptional, (87)
"Our room was perfect for our weekend visit with friends who lived nearby. The room had everything we needed and was very close to the lake, which has a lovely walking path. Our hosts were kind and helpful."
United States
Julia H.
$97 nightly
The price is $110
Dec 24 - Dec 25
Total with taxes and fees
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Interior
KK lower · Funky 2BR in Prime Bay View - w/ Parking

Vacation Home in Bay View

KK lower · Funky 2BR in Prime Bay View - w/ Parking
10.0 out of 10, Exceptional, (7)
"Charming apartment, convenient location"
United States
Ashton G.
$194 nightly
The price is $198
Jan 13 - Jan 14, 2026
Total with taxes and fees
KK lower · Funky 2BR in Prime Bay View - w/ Parking
Dining
Whole House in Bay View + Fenced-in Yard + Parking

Vacation Home in Bay View

Whole House in Bay View + Fenced-in Yard + Parking
10.0 out of 10, Exceptional, (11)
"was great and close to our daughter"
United States
Nicholas S.
$338 nightly
The price is $399
Dec 29 - Dec 30
Total with taxes and fees
Whole House in Bay View + Fenced-in Yard + Parking
Exterior
comfortably sleeps 10 guests

Vacation Home in Elkhorn

comfortably sleeps 10 guests
10.0 out of 10, Exceptional, (41)
"Great place, great manager "
United States
Chris C.
$423 nightly
The price is $429
Dec 25 - Dec 26
Total with taxes and fees
comfortably sleeps 10 guests
TV, fireplace
Exclusive Brownstone Residence

Vacation Home in Halyard Park

Exclusive Brownstone Residence
2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a nice stay at this property and hope to do it again "
United States
Damien S.
$190 nightly
The price is $224
Dec 24 - Dec 25
Total with taxes and fees
Exclusive Brownstone Residence
Dining
Quick Trip Getaway |Fun Southwestern Vibe |Enclosed Porch |Walkable to Downtown Lake Geneva |Parking

Vacation Home in Lake Geneva

Quick Trip Getaway |Fun Southwestern Vibe |Enclosed Porch |Walkable to Downtown Lake Geneva |Parking
9.8 out of 10, Exceptional, (29)
"The location was easy to find and perfect walking distance to downtown. "
United States
Griffin Y.
$363 nightly
The price is $412
Dec 27 - Dec 28
Total with taxes and fees
Quick Trip Getaway |Fun Southwestern Vibe |Enclosed Porch |Walkable to Downtown Lake Geneva |Parking
Smart TV, computer monitors
Charming 2-bedroom house with everything you need in the heart of West Allis

Vacation Home in West Allis

Charming 2-bedroom house with everything you need in the heart of West Allis
9.6 out of 10, Exceptional, (4)
"Had a great weekend stay. House was clean and cute and our host was very accommodating!"
United States
Renee W.
Charming 2-bedroom house with everything you need in the heart of West Allis
Dining
Potter Lower · Funky 2.5BR in the Heart of Bay View - w/ Parking

Vacation Home in Bay View

Potter Lower · Funky 2.5BR in the Heart of Bay View - w/ Parking
9.4 out of 10, Exceptional, (15)
"We loved this property! We will definitely stay again if we are in the area."
United States
Taryn O.
$223 nightly
The price is $228
Jan 12 - Jan 13, 2026
Total with taxes and fees
Potter Lower · Funky 2.5BR in the Heart of Bay View - w/ Parking
Smart TV
Vibrant Milwaukee Townhome near Downtown

Vacation Home in Riverwest

Vibrant Milwaukee Townhome near Downtown
8.0 out of 10, Very Good, (2)
"This is a cool, fun neighborhood! It’s really central to pretty much everything and close to downtown. The property is cozy and is a nice place to hang out. We had a wonderful time! "
United States
Thomas S.
$222 nightly
The price is $261
Jan 2 - Jan 3, 2026
Total with taxes and fees
Vibrant Milwaukee Townhome near Downtown
Outdoor dining
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

Vacation Home in Johnson Woods

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
9.8 out of 10, Exceptional, (26)
"We stayed while attending the WI state fair. Quiet and safe neighborhood and really close to the fairgrounds. House was clean and easy to get to. We enjoyed our stay and the fenced in backyard was perfect for our Frenchie. "
United States
Roy W.
$281 nightly
The price is $331
Jan 1 - Jan 2, 2026
Total with taxes and fees
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Beach nearby
2bed 1.5bath House, Lower Eastside, King Bed, Fire Pit, Sleeps 6

Vacation Home in Downtown Milwaukee

2bed 1.5bath House, Lower Eastside, King Bed, Fire Pit, Sleeps 6
10.0 out of 10, Exceptional, (1)
"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.
$344 nightly
The price is $406
Dec 29 - Dec 30
Total with taxes and fees
2bed 1.5bath House, Lower Eastside, King Bed, Fire Pit, Sleeps 6
Smart TV, books, music library, stereo
Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer

Vacation Home in Bay View

Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer
2.0 star property
10.0 out of 10, Exceptional, (27)
"Very comfortable and convenient to everything downtown."
United States
Reddemann R.
$355 nightly
The price is $419
Dec 24 - Dec 25
Total with taxes and fees
Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer
Fridge, microwave, oven, stovetop
Cozy Home In Lake Geneva WI Area

Vacation Home in Lake Geneva

Cozy Home In Lake Geneva WI Area
8.8 out of 10, Excellent, (16)
"Super clean,quiet house! Close to water for us to launch our boat. We would definitely stay again, Thank You"
United States
kelly b.
$205 nightly
The price is $227
Jan 21 - Jan 22, 2026
Total with taxes and fees
Cozy Home In Lake Geneva WI Area
Dining
Three bedrooms upstairs

Vacation Home in Riverwest

Three bedrooms upstairs
9.6 out of 10, Exceptional, (78)
"He was very kind!"
United States
Hope
$199 nightly
The price is $234
Dec 30 - Dec 31
Total with taxes and fees
Three bedrooms upstairs
Interior
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

Vacation Home in Lower East Side

NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
2.0 star property
9.8 out of 10, Exceptional, (20)
"Great property for our family group for a long weekend in Milwaukee. "
United States
Karl S.
$363 nightly
The price is $428
Jan 14 - Jan 15, 2026
Total with taxes and fees
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
Property grounds
Peaceful East Side-2 min UWM-Dining-Coffee-Parking

Vacation Home in Upper East Side

Peaceful East Side-2 min UWM-Dining-Coffee-Parking
10.0 out of 10, Exceptional, (5)
"Great property and a great location. Lulu was an incredible and thoughtful host. "
United States
Lori B.
$241 nightly
The price is $284
Dec 27 - Dec 28
Total with taxes and fees
Peaceful East Side-2 min UWM-Dining-Coffee-Parking
Exterior
Horse lovers paradise with 2 bedrooms and WiFi, AC in Lake Geneva

Vacation Home in Lake Geneva

Horse lovers paradise with 2 bedrooms and WiFi, AC in Lake Geneva
10.0 out of 10, Exceptional, (10)
"Beautiful place! We loved our mornings walk, watching the horses and goats, and the barn tour! The host was great! "
United States
Scott G.
$294 nightly
The price is $328
Dec 29 - Dec 30
Total with taxes and fees
Horse lovers paradise with 2 bedrooms and WiFi, AC in Lake Geneva
Interior
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Vacation Home in Waukesha

Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
9.8 out of 10, Exceptional, (19)
"Will come and stay again great host and home"
United States
Dion S.
$269 nightly
The price is $304
Jan 4 - Jan 5, 2026
Total with taxes and fees
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
Microwave, oven, stovetop
Cozy & Quiet, dog-friendly 2-bedroom Upper in Central Milwaukee

Vacation Home in Fair Park

Cozy & Quiet, dog-friendly 2-bedroom Upper in Central Milwaukee
2.0 star property
$264 nightly
The price is $311
Jan 2 - Jan 3, 2026
Total with taxes and fees
Cozy & Quiet, dog-friendly 2-bedroom Upper in Central Milwaukee
Exterior
Rare East Side-2 min walk to UWM-Garage-Lake Mich

Vacation Home in Upper East Side

Rare East Side-2 min walk to UWM-Garage-Lake Mich
10.0 out of 10, Exceptional, (2)
"Loved our stay. Nice clean place that was well stocked."
United States
Patty S.
$241 nightly
The price is $284
Dec 24 - Dec 25
Total with taxes and fees
Rare East Side-2 min walk to UWM-Garage-Lake Mich
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

Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

10/10 Excellent
"From check in to check out staff and facilities were great! "
Leslie 1-night trip
Posted 1 day ago
Drury Plaza Hotel Milwaukee Downtown

Find out more about Southeast Wisconsin

Southeast Wisconsin Vacation Homes information

Number of reviews
386
Accommodation
826 Vacation Homes
Lowest Price
$110
Highest Price
$429

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