Holiday Rentals in Southeast Wisconsin

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Holiday Rentals in Southeast Wisconsin

Timber Ridge Lodge and Waterpark

3.5 star property
8.6 out of 10, Excellent, (3006)
"Loved the stay staff went above and beyond will be back "
The price is €166
includes taxes & fees
15 Oct - 16 Oct
Timber Ridge Lodge and Waterpark

The Plaza Hotel

3.0 star property
8.8 out of 10, Excellent, (1142)
"Loved this hotel! Clean friendly and cute!!"
The price is €156
includes taxes & fees
3 Nov - 4 Nov
The Plaza Hotel

Mill Creek Hotel

2.5 star property
9.2 out of 10, Wonderful, (1205)
"Enjoyed our stay, perfect location !"
The price is €153
includes taxes & fees
2 Nov - 3 Nov
Mill Creek Hotel

Kasa Westown Milwaukee

4.0 star property
9.0 out of 10, Wonderful, (104)
"Very nice apartment and right down town location is perfect!"
Kasa Westown Milwaukee

Experience Stay at the Glamping Loft Lake Geneva |Group Stays |Stylish Tent Suites |Kitchen & Bar

10.0 out of 10, Exceptional, (31)
"We came to Wisconsin for a bachelorette party! This place was described perfectly and was absolutely perfect for our girls! We are very very pleased and would recommend this highly!"
The price is €724
includes taxes & fees
13 Oct - 14 Oct
Experience Stay at the Glamping Loft Lake Geneva |Group Stays |Stylish Tent Suites |Kitchen & Bar

Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage

9.8 out of 10, Exceptional, (106)
"Had a wonderful stay. Tony and Samantha were great through the process and our stay. Highly recommend"
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage

THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20

9.8 out of 10, Exceptional, (192)
"Wonderful property. Clean with lots of space. Excellent location. Easy communication with host. Will return we."
THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20

KLVG - Malt House

4.0 star property
8.8 out of 10, Excellent, (10)
"Loved the uniqueness, location and cleanliness of the unit."
KLVG - Malt House

Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking

9.8 out of 10, Exceptional, (93)
"Located right in town with a view of the lake and beach with a wonderful balcony."
The price is €460
includes taxes & fees
15 Oct - 16 Oct
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking

Lakefront Haven: Waterfront Oasis with Dock, Spacious Swim Pier & Pano Lake view

2.5 star property
10.0 out of 10, Exceptional, (10)
"We had this fabulous home during the fourth of July week for our family vacation. Kyle was a wonderful host and checked in with us often to make sure everything was perfect. Highly recommend this Super Host Property."
Lakefront Haven: Waterfront Oasis with Dock, Spacious Swim Pier & Pano Lake view

Private Country House near Lake Geneva, Como and Williams Bay

10.0 out of 10, Exceptional, (92)
"Good place to stay nice location "
Private Country House near Lake Geneva, Como and Williams Bay

7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool

9.8 out of 10, Exceptional, (212)
"Great place to stay! "
The price is €618
includes taxes & fees
22 Oct - 23 Oct
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool

10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

9.6 out of 10, Exceptional, (12)
"The house was great. The pool temp was very warm when we arrived we did our best to cool it down. We really enjoyed the stay."
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva

2.0 star property
9.4 out of 10, Exceptional, (12)
"Had a great trip and the property was perfect for the 4 of us. Really appreciated the accessible shower."
The price is €228
includes taxes & fees
27 Oct - 28 Oct
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

10.0 out of 10, Exceptional, (247)
"Beautiful view, wonderful house. Great morings with coffee on balcony!!"
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle

9.0 out of 10, Wonderful, (4)
"The house was absolutely perfect for our group. The backyard was a great area for our group to get together play yard games and be able to enjoy the lake at the same time. For the few hours of rain we experienced, we were able to enjoy the fun arcade games in the basement to pass our time. Oh and how could I forget the indoor pool!Katie was a wonderful host. Great communication and she was readily available to help us on the property if any requests were asked. She is very knowledgeable about...
Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle

KB - Prospec

3.0 star property
7.6 out of 10, Good, (7)
"Our stay was great. The property was at it was described and expected. The owner was available via text and communicated with me when I had questions. We would stay again!"
KB - Prospec

Three bedrooms upstairs

9.6 out of 10, Exceptional, (74)
"The property was cute and stylish. I would stay here again. "
The price is €206
includes taxes & fees
12 Oct - 13 Oct
Three bedrooms upstairs

Best Location in Lake Geneva, walk to downtown!

10.0 out of 10, Exceptional, (19)
"Amazing location wtih ease of access to anything you want to do downtown. "
Best Location in Lake Geneva, walk to downtown!

#2 Tamarack aka Como Escape · Como Escape 4 bed 3 bath by LAKE

10.0 out of 10, Exceptional, (31)
"Excellent Stay"
The price is €403
includes taxes & fees
28 Oct - 29 Oct
#2 Tamarack aka Como Escape · Como Escape 4 bed 3 bath by LAKE
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

Find out more about Southeast Wisconsin

Find out more about Southeast Wisconsin

Everything you need to know about Southeast Wisconsin holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southeast Wisconsin holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Southeast Wisconsin holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southeast Wisconsin holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southeast Wisconsin holiday rentals we have selected for you start as low as €153 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southeast Wisconsin rentals

At Expedia, we put the best Southeast Wisconsin holiday 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 holiday.

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.