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
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Southeast Wisconsin vacation rentals

Water park

1. Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark
3.5 star property
Lake Geneva
8.6 out of 10, Excellent, (3,346 reviews)
"Very family friendly, kids had a blast."
United States
Brandon
$287 nightly
The price is $320
Aug 31 - Sep 1
Total with taxes and fees
Timber Ridge Lodge and Waterpark
Premier Room, 1 King Bed | Iron/ironing board, WiFi (free), bed sheets

2. The Plaza Hotel

The Plaza Hotel
3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1,218 reviews)
"charming and historic hotel"
United States
Veronica
$183 nightly
The price is $216
Aug 10 - Aug 11
Total with taxes and fees
The Plaza Hotel
Indoor pool, sun loungers

3. Mill Creek Hotel

Mill Creek Hotel
2.5 star property
Lake Geneva
9.2 out of 10, Wonderful, (1,248 reviews)
"Highly recommend."
United States
Laurie
$253 nightly
The price is $287
Sep 1 - Sep 2
Total with taxes and fees
Mill Creek Hotel
Interior

4. 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, (37 reviews)
"Awesome stay, awesome house and great communication with owner. "
United States
Tom F.
$344 nightly
The price is $389
Aug 11 - Aug 12
Total with taxes and fees
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
Fireplace

5. Kasa Westown Milwaukee

Kasa Westown Milwaukee
4.0 star property
Westown
9.0 out of 10, Wonderful, (142 reviews)
"Nice apartment in a good location in the brewery district. Clean and comfortable and safe. Laundry in apartment was a bonus. ."
United States
Steven
$197 nightly
The price is $232
Aug 19 - Aug 20
Total with taxes and fees
Kasa Westown Milwaukee
Smart TV, table tennis, printers

6. 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, (53 reviews)
" Very comfortable, had everything we needed, convenient, and pet friendly. A great Greendale Original."
United States
Thomas S. A.
$335 nightly
The price is $365
Aug 17 - Aug 18
Total with taxes and fees
Historic home - walk to village center. Original features with modern updates.
Exterior

7. Family-Friendly 5-BR Near Stadium - Tv's In Every Room + New Kitchen

Family-Friendly 5-BR Near Stadium - Tv's In Every Room + New Kitchen
West Allis
8.4 out of 10, Very Good, (20 reviews)
"Very nice place and comfortable beds indeed."
United States
Lisa C.
$518 nightly
The price is $605
Aug 3 - Aug 4
Total with taxes and fees
Family-Friendly 5-BR Near Stadium - Tv's In Every Room + New Kitchen
1 bedroom, WiFi (free)

8. 1 King Bed | Non-Smoking, Kitchen

1 King Bed | Non-Smoking, Kitchen
Milwaukee WI
9.6 out of 10, Exceptional, (37 reviews)
"Love this place"
United States
Anonymous traveler
$86 nightly
The price is $97
Aug 31 - Sep 1
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen
Exterior

9. Charming Historic Upper Walk to Downtown & Lakes

Charming Historic Upper Walk to Downtown & Lakes
Oconomowoc
10.0 out of 10, Exceptional, (41 reviews)
"Very cute and clean property. Location was great - walk to coffee, dinner etc."
United States
Stephanie B.
$534 nightly
The price is $604
Aug 3 - Aug 4
Total with taxes and fees
Charming Historic Upper Walk to Downtown & Lakes
Dining

10. Three Bedroom Upper

Three Bedroom Upper
Riverwest
9.6 out of 10, Exceptional, (97 reviews)
"Great stay comfortable place I would most definitely come back "
United States
Crystiana H.
$199 nightly
The price is $234
Aug 9 - Aug 10
Total with taxes and fees
Three Bedroom Upper
Smart TV, books, music library, stereo

11. Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer

Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer
Bay View
10.0 out of 10, Exceptional, (35 reviews)
"We absolutely loved our time at Robin’s lovely home! It was so welcoming and charming! We loved the Rootbeer floats and the Easter decor/candy! Definitely will recommend to friends and family!"
United States
T.R. M.
$376 nightly
The price is $443
Aug 10 - Aug 11
Total with taxes and fees
Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer
Exterior

12. Downtown Eastside gem near Fiserv Forum Water St Brady St

Downtown Eastside gem near Fiserv Forum Water St Brady St
Downtown Milwaukee
9.0 out of 10, Wonderful, (58 reviews)
"Bed was very comfortable."
United States
Derek C.
$280 nightly
The price is $330
Aug 3 - Aug 4
Total with taxes and fees
Downtown Eastside gem near Fiserv Forum Water St Brady St
Outdoor dining

13. 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, (43 reviews)
"Prompt and helpful host. Was as advertised. Great location."
United States
Jason N.
$339 nightly
The price is $400
Sep 1 - Sep 2
Total with taxes and fees
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Smart TV, books

14. Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly

Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly
Murray Hill
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful house, excellent location, attentive host! It was a great stay! "
United States
Cary W.
$466 nightly
The price is $550
Aug 11 - Aug 12
Total with taxes and fees
Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly
Beach nearby

15. Charming home w/ fire pit, walk to Lake Michigan

Charming home w/ fire pit, walk to Lake Michigan
Shorewood
10.0 out of 10, Exceptional, (48 reviews)
"Great place so cute....walk to grocery shop"
United States
Annette A.
$369 nightly
The price is $402
Aug 24 - Aug 25
Total with taxes and fees
Charming home w/ fire pit, walk to Lake Michigan
Smart TV, computer monitors

16. Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms

Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms
Bay View
10.0 out of 10, Exceptional, (20 reviews)
"Best stay"
United States
Marvin G.
$625 nightly
The price is $737
Aug 23 - Aug 24
Total with taxes and fees
Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms
Property grounds

17. Waterfront Lake Cottage - Upper Nemahbin Lake

Waterfront Lake Cottage - Upper Nemahbin Lake
Peninsular Park
9.6 out of 10, Exceptional, (36 reviews)
"Our stay couldn’t have been better! Gorgeous place on the water. Hosts were super helpful and accommodating."
United States
Erin M.
$686 nightly
The price is $720
Sep 1 - Sep 2
Total with taxes and fees
Waterfront Lake Cottage - Upper Nemahbin Lake
Game room

18. Tranquil Downtown Haven | 3-Bed, 2-Bath Delight

Tranquil Downtown Haven | 3-Bed, 2-Bath Delight
Downtown Milwaukee
9.0 out of 10, Wonderful, (14 reviews)
"Host was great, good communication "
United States
Ry M.
$750 nightly
The price is $767
Aug 14 - Aug 15
Total with taxes and fees
Tranquil Downtown Haven | 3-Bed, 2-Bath Delight
TV

19. Large Victorian in Perfect Location!

Large Victorian in Perfect Location!
Downtown Milwaukee
10.0 out of 10, Exceptional, (33 reviews)
"Very nice house managed by very nice people. Will stay here again. "
United States
Robert S.
$1,198 nightly
The price is $1,323
Aug 4 - Aug 5
Total with taxes and fees
Large Victorian in Perfect Location!
Exterior

20. Horse lovers paradise with 2 bedrooms and WiFi, AC in Lake Geneva

Horse lovers paradise with 2 bedrooms and WiFi, AC in Lake Geneva
Lake Geneva
10.0 out of 10, Exceptional, (21 reviews)
"The setting is perfect, and the apartment is spacious and comfortable."
United States
Marsha S.
$294 nightly
The price is $328
Aug 3 - Aug 4
Total with taxes and fees
Horse lovers paradise with 2 bedrooms and WiFi, AC in Lake Geneva
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 Pfister Hotel

The Pfister Hotel

10/10 Excellent
"We had a great experience at the Pfister. The food at the cafe was delicious. The staff could not have been more helpful. The rooms were well appointed and comfortable. Highly recommend."
Margaret 2-night trip
Posted 3 hours ago
The Pfister Hotel

Find out more about Southeast Wisconsin

Everything you need to know about Southeast Wisconsin vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southeast Wisconsin vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southeast Wisconsin vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southeast Wisconsin vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southeast Wisconsin. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southeast Wisconsin in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $216 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southeast Wisconsin rentals

At Expedia, we put the best Southeast Wisconsin vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southeast Wisconsin rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southeast Wisconsin vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southeast Wisconsin. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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