Southeast Wisconsin Vacation Rentals

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Vacation Rentals in Southeast Wisconsin

Water park
Timber Ridge Lodge and Waterpark

Aparthotel in Lake Geneva

3.5 star property
8.6 out of 10, Excellent, (3056)
"Very nice room and fun waterpark. "
United States
Kristi
$194 nightly
The price is $216
Dec 8 - Dec 9
Total with taxes and fees
Timber Ridge Lodge and Waterpark
Premier Room, 1 King Bed | Iron/ironing board, free WiFi, bed sheets
The Plaza Hotel

Aparthotel in Downtown Milwaukee

3.0 star property
8.8 out of 10, Excellent, (1153)
"Loved this hotel! Clean friendly and cute!!"
United States
Sharon H
$156 nightly
The price is $184
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Plaza Hotel
Indoor spa tub
Mill Creek Hotel

Aparthotel in Lake Geneva

2.5 star property
9.2 out of 10, Wonderful, (1217)
"Enjoyed our stay, perfect location !"
United States
Lisa
$157 nightly
The price is $178
Dec 4 - Dec 5
Total with taxes and fees
Mill Creek Hotel
Fireplace
Kasa Westown Milwaukee

Aparthotel in Westown

4.0 star property
9.0 out of 10, Wonderful, (117)
"Perfect location, so many things were within walking distance. Also felt very safe and more convenient than a hotel room. "
United States
Kaylee
$143 nightly
The price is $169
Dec 4 - Dec 5
Total with taxes and fees
Kasa Westown Milwaukee
Terrace/patio
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

Vacation Home in New Berlin

8.4 out of 10, Very Good, (8)
"We had an excellent family vacation at The Garden of Eden!!"
United States
Cheryl S.
$1,997 nightly
The price is $2,256
Dec 8 - Dec 9
Total with taxes and fees
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18
Billiards
ROVE LIVING/KL - Malt House

Apartment in Westown

4.0 star property
8.8 out of 10, Excellent, (10)
"Loved the uniqueness, location and cleanliness of the unit."
United States
Teresa
$151 nightly
The price is $179
Dec 4 - Dec 5
Total with taxes and fees
ROVE LIVING/KL - Malt House
Outdoor pool, a heated pool
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

Vacation Home in Caledonia

9.8 out of 10, Exceptional, (213)
"I want to move in. We had 13 guys for a bachelor retreat and this place was perfect. Plenty of room for us all and plenty to do. We expected to spend plenty of time exploring Milwaukee, but found ourselves hanging out at the pool or fishing in the pond when we weren’t relaxing in the game room. 10/10 would recommend!"
United States
Caleb B.
$657 nightly
The price is $693
Dec 21 - Dec 22
Total with taxes and fees
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!
Fridge, microwave, oven, stovetop
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage

Vacation Home in Lake Geneva

9.8 out of 10, Exceptional, (108)
"Property was perfect for our group. We arrived to a clean home, everything was as advertised and hosts were very accommodating. Location was perfect, walking distance from downtown lake Geneva."
United States
David C.
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage
Indoor pool, a heated pool
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

Vacation Home in Burlington

9.6 out of 10, Exceptional, (12)
"Great Stay while in town for Country Thunder. The host was very accommodating and easy to communicate with. Would absolutely stay here again in the future if travels bring me to this part of the country!"
United States
Ronald G.
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna
Fridge, microwave, oven, stovetop
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva

Vacation Home in Lake Geneva

2.0 star property
9.4 out of 10, Exceptional, (14)
"Had a great trip and the property was perfect for the 4 of us. Really appreciated the accessible shower."
United States
Bret S.
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva
Smart TV, fireplace
Lakeside Loft! Updated 2 BR condo/Close to Lodge & GN/Outdoor Pool/Free Parking

Condo in Lake Geneva

10.0 out of 10, Exceptional, (6)
$312 nightly
The price is $347
Dec 4 - Dec 5
Total with taxes and fees
Lakeside Loft! Updated 2 BR condo/Close to Lodge & GN/Outdoor Pool/Free Parking
Fridge, microwave, oven, stovetop
Wooded Hills/Indoor Pool/Hot Tub/Arcade

Vacation Home in Sussex

9.8 out of 10, Exceptional, (50)
"Wonderful property. Host was extremely responsive and helpful."
United States
joan r.
Wooded Hills/Indoor Pool/Hot Tub/Arcade
Terrace/patio
THE ULTIMATE 6 BEDROOM LAKEHOUSE

Vacation Home in Lake Geneva

9.6 out of 10, Exceptional, (40)
"Wonderful house, perfect for a weekend stay. Great views and more than enough space?"
United States
John M.
$1,294 nightly
The price is $1,443
Dec 7 - Dec 8
Total with taxes and fees
THE ULTIMATE 6 BEDROOM LAKEHOUSE
Dining
Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle

Vacation Home in Oconomowoc

10.0 out of 10, Exceptional, (3)
"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...
United States
Billy L.
Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle
Terrace/patio
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!

Vacation Home in Burlington

9.8 out of 10, Exceptional, (93)
"Hosts went above and beyond to accommodate my senior mother with a private bed on main level. They were also accommodating on other requests that I had. It was such a fun, nostalgic place. It was all exactly how I remembered the Old Mill to be and the private beach made for some additional family time. I see a wonderful future for this getaway place!! "
United States
Tina V.
$629 nightly
The price is $664
Dec 4 - Dec 5
Total with taxes and fees
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Outdoor dining
Private Country House near Lake Geneva, Como and Williams Bay

Vacation Home in Lake Geneva

10.0 out of 10, Exceptional, (94)
"Excellent bedrooms & baths. Cogregating areas large and well done."
United States
Gerald F.
Private Country House near Lake Geneva, Como and Williams Bay
Smart TV, fireplace, DVD player, books
Private Beach & Pier Lake Front w/ Fireplace on Lake Como - Walk to Mars Resort!

Vacation Home in Lake Geneva

10.0 out of 10, Exceptional, (317)
"Our family loved this property for a week of relaxation. The house was very clean and well stocked. We had zero issues from the check-in to check-out. "
United States
MaryJane S.
Private Beach & Pier Lake Front w/ Fireplace on Lake Como - Walk to Mars Resort!
Property grounds
Harbor & Hearth a Modern Lakefront Condo w/ Pool, Spa & Dining On The Lake

Condo in Lake Geneva

9.0 out of 10, Wonderful, (70)
"Loved the location and accessibility to so many things. Everything we needed was there. Thank you"
United States
Jane Burden B.
$244 nightly
The price is $272
Dec 4 - Dec 5
Total with taxes and fees
Harbor & Hearth a Modern Lakefront Condo w/ Pool, Spa & Dining On The Lake
Property grounds
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

Vacation Home in Kenosha

10.0 out of 10, Exceptional, (249)
"The house was a great place for our family of nine to relax and spacious enough for us to have our own rooms. "
United States
Linda M.
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Dining room
ROVE LIVING/KB - Prospect

Apartment in Lower East Side

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!"
United States
Vera
ROVE LIVING/KB - Prospect
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 Brewhouse Inn & Suites

The Brewhouse Inn & Suites

10/10 Excellent
"Wish we could have had time to go to the taproom. Very cool interior with friendly efficient staff. We would stay again."
Serra 1-night trip
Posted 2 days ago
The Brewhouse Inn & Suites

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 $169 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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