Southeast Wisconsin Vacation Rentals from $158: Search Short-Term Rentals

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Our top choices for Southeast Wisconsin vacation rentals

A hotel with a large outdoor pool, lounge chairs, and a water slide.

1. Timber Ridge Lodge and Waterpark

Lake Geneva

Lindsey

$169 nightly

Dec 9 - Dec 10

Total with taxes and fees

An outdoor patio area with tables and chairs, surrounded by lush green ivy walls, and a brick building in the background.

2. The Plaza Hotel

Downtown Milwaukee

Savannah

$134 nightly

Nov 22 - Nov 23

Total with taxes and fees

A modern kitchen with a large island, dark cabinetry, stainless steel appliances, and a city view through large windows.

3. Modern Luxury 1BR Apt with Rooftop, Gym, and Parking

Westown

Elizabeth

$117 nightly

Nov 22 - Nov 23

Total with taxes and fees

A compact kitchenette with a stove, sink, and microwave, a mirror, and a door with a notice.

4. 2 Queen Beds | Mobil Access Tub Nsmk Kitchen

Milwaukee WI

Anonymous traveler

$84 nightly

Nov 25 - Nov 26

Total with taxes and fees

An indoor swimming pool with wooden walls and ceiling, surrounded by lounge chairs and potted plants.

5. Mill Creek Hotel

Lake Geneva

Marshall

$186 nightly

Nov 15 - Nov 16

Total with taxes and fees

A room with a large window overlooking a city street, a brown leather sofa, and a small wooden table.

6. Deer District Studio Apt - One Block from Fiserv and Baird

Westown

Thomas G.

$113 nightly

Nov 22 - Nov 23

Total with taxes and fees

A modern living room with a sofa, armchair, and a TV.

7. Westown Studio Apt Near Fiserv, Baird, and Theater District

Westown

william w.

$111 nightly

Nov 19 - Nov 20

Total with taxes and fees

A patio area with outdoor seating and a fire feature, surrounded by greenery and overlooking a body of water.

8. Lake Geneva, Fireplace, Pool, Wifi, King Bed

Lake Geneva

SUZY R.

$232 nightly

Nov 12 - Nov 13

Total with taxes and fees

A spacious indoor area with a high ceiling, metal beams, and a central seating area with sofas.

9. Cream City Industrial Loft Near Fiserv with Parking | Suite 4 | Sleeps 8

Westown

Mary W.

$125 nightly

Nov 12 - Nov 13

Total with taxes and fees

A bedroom with a bed, bedside table, lamp, and a painting on the wall.

10. Near Froedtert MCW with Garage Pkg and King Bed

Wauwatosa

Jenna F.

$382 nightly

Nov 16 - Nov 17

Total with taxes and fees

A two-story building with a balcony, labeled "Ole Bistro Inn" and "Vacation Rental."

11. Top location, no cleaning fee, everthings close B

Lake Geneva

Justin G.

$151 nightly

Nov 12 - Nov 13

Total with taxes and fees

A multi-story building with a prominent entrance, large windows, and a flag.

12. Luxury Downtown Apt with Parking, Gym, and Lap Pool · Sleeps 4-5

Downtown Milwaukee

David B.

$140 nightly

Nov 15 - Nov 16

Total with taxes and fees

A stone building with a red sign reading "Kegler Inn."

13. Kegel`s Inn - Studio - Classic Apartment #3

West Allis

Zachary

$160 nightly

Nov 12 - Nov 13

Total with taxes and fees

A house with a front porch, steps, and a small garden area.

14. Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Kenosha

Erin

$77 nightly

Nov 15 - Nov 16

Total with taxes and fees

A hotel room with a bed, a sofa, a chair, a TV, a desk, and a balcony with a view of buildings.

15. Walker`s Point Designer 2BR · Prime Location with Balcony and Gym · Sleeps 6

Fifth Ward

Erin G.

$135 nightly

Nov 12 - Nov 13

Total with taxes and fees

A modern kitchen with a large island, stainless steel sink, and pendant lights.

16. Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Waukesha

Jason d.

$316 nightly

Nov 16 - Nov 17

Total with taxes and fees

A dining area with a brick wall, a wooden table, black chairs, and a potted plant.

17. Hidden Gem with Pool View!

Lake Geneva

Thomas P.

$238 nightly

Nov 16 - Nov 17

Total with taxes and fees

Stop into the Welcome Center on Grand Ave downtown. Be sure to say hello to Wayne and Amy. They are so helpful in guiding you to all things Port. Tell them Dave and Janice sent you. Or find them at https://www.visitportwashington.com/

18. Grace Adventure House, walk to Port, Lake Michigan

Port Washington

Sherrie P.

$206 nightly

Nov 12 - Nov 13

Total with taxes and fees

A hotel room with a bed, a TV mounted on the wall, a wooden door, and a small table with a plant.

19. Walk to Tosa Village | Cafés & Shops | King Bed

Wauwatosa

Margaret M.

$279 nightly

Dec 2 - Dec 3

Total with taxes and fees

A modern living room with a green sofa, a white coffee table, and a ceiling fan.

20. Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom

Lake Geneva

Denise A.

$260 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Top Southeast Wisconsin Hotel Reviews

AmericInn by Wyndham Brookfield

10/10 Excellent

"The rooms were clean, saff was helpful breakfast was good. I recommend this place."

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

8/10 Good

"This is an older hotel in an art deco style. There were some quirks but it was unique and interesting! It had a very good restaurant and bar and all the staff were excellent at what they did. The bar had great cocktails and the kitchen was open until 12 and bar until 2 am on Friday & Saturday (10/12 on Sunday). The hotel offered a shuttle service to downtown but it filled up quickly on Friday and Saturday evenings. Strongly recommend making a reservation for those times. We walked downtown a couple of times and it wasn’t a bad walk. We had a really nice stay."

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 $158 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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Check prices for these dates

Our top choices for Southeast Wisconsin vacation rentals

1. Timber Ridge Lodge and Waterpark

2. The Plaza Hotel

3. Modern Luxury 1BR Apt with Rooftop, Gym, and Parking

4. 2 Queen Beds | Mobil Access Tub Nsmk Kitchen

5. Mill Creek Hotel

6. Deer District Studio Apt - One Block from Fiserv and Baird

7. Westown Studio Apt Near Fiserv, Baird, and Theater District

8. Lake Geneva, Fireplace, Pool, Wifi, King Bed

9. Cream City Industrial Loft Near Fiserv with Parking | Suite 4 | Sleeps 8

10. Near Froedtert MCW with Garage Pkg and King Bed

11. Top location, no cleaning fee, everthings close B

12. Luxury Downtown Apt with Parking, Gym, and Lap Pool · Sleeps 4-5

13. Kegel`s Inn - Studio - Classic Apartment #3

14. Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

15. Walker`s Point Designer 2BR · Prime Location with Balcony and Gym · Sleeps 6

16. Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

17. Hidden Gem with Pool View!

18. Grace Adventure House, walk to Port, Lake Michigan

19. Walk to Tosa Village | Cafés & Shops | King Bed

20. Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom

Find vacation rentals that suit your style

Top Southeast Wisconsin Hotel Reviews

AmericInn by Wyndham Brookfield

Sheraton Milwaukee Brookfield Hotel

The Pfister Hotel

The Cove Of Lake Geneva

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI

Ramada by Wyndham Milwaukee

Grand Geneva Resort & Spa

Find out more about Southeast Wisconsin

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