Waukesha Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Waukesha holiday rentals

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, (19)
"Will come and stay again great host and home"
United States
Dion S.
The price is NZ$549
includes taxes & fees
4 Jan - 5 Jan 2026
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

The Plaza Hotel

The Plaza Hotel
3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1153)
"Loved this hotel! Clean friendly and cute!!"
United States
Sharon H
The price is NZ$278
includes taxes & fees
12 Jan - 13 Jan 2026
The Plaza Hotel

Kasa Westown Milwaukee

Kasa Westown Milwaukee
4.0 star property
Westown
9.0 out of 10, Wonderful, (119)
"Hosts get 5 stars for excellent communication. They checked in with me multiple times on my day of arrival to make sure everything was good and they gave very thorough instructions."
United States
Melissa
Kasa Westown Milwaukee

ROVE LIVING/KL - Malt House

ROVE LIVING/KL - Malt House
4.0 star property
Westown
9.0 out of 10, Wonderful, (11)
"The room was clean and spacious and very comfy the property was as well very beautiful and so much to look at … my family enjoyed the games that were in the room as well. We will definitely stay their again for our next visit "
United States
Ivan
The price is NZ$284
includes taxes & fees
18 Dec - 19 Dec
ROVE LIVING/KL - Malt House

7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!
Caledonia
9.8 out of 10, Exceptional, (213)
"It was nice "
United States
Kevin C.
The price is NZ$1,120
includes taxes & fees
21 Dec - 22 Dec
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18
New Berlin
7.8 out of 10, Good, (10)
"Awesome place!"
United States
Daniel M.
The price is NZ$3,133
includes taxes & fees
22 Dec - 23 Dec
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

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

10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna
Burlington
9.6 out of 10, Exceptional, (12)
"Very nice layout with lots of rooms and interesting places to be for a large group or family"
United States
Brian M.
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

ROVE LIVING/KB - Prospect

ROVE LIVING/KB - Prospect
3.0 star property
Lower East Side
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

Wooded Hills/Indoor Pool/Hot Tub/Arcade

Wooded Hills/Indoor Pool/Hot Tub/Arcade
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

Three bedrooms upstairs

Three bedrooms upstairs
Riverwest
9.6 out of 10, Exceptional, (78)
"He was very kind!"
United States
Hope
The price is NZ$403
includes taxes & fees
17 Dec - 18 Dec
Three bedrooms upstairs

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

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

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, (46)
"The check in instructions were perfect and not sure he could have laid that out any better. It's a nice place close to everything. We'd stay there again. "
United States
Chad-Tara A.
The price is NZ$571
includes taxes & fees
27 Dec - 28 Dec
Downtown Eastside gem near Fiserv Forum Water St Brady St

Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Lower East Side
9.6 out of 10, Exceptional, (67)
"It was clean and close to our wedding venue. "
United States
Kathy H.
The price is NZ$750
includes taxes & fees
20 Dec - 21 Dec
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

Renovated Brady St. Classic

Renovated Brady St. Classic
Downtown Milwaukee
8.4 out of 10, Very good, (10)
"Comfortable property in a great location. Liked that my adult children could walk to nearby restaurants, shops and bars. Neighborhood parking is limited, but not unusual for downtown-type stays."
United States
Mike F.
Renovated Brady St. Classic

NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
2.0 star property
Lower East Side
9.8 out of 10, Exceptional, (20)
"Great property for our family group for a long weekend in Milwaukee. "
United States
Karl S.
The price is NZ$728
includes taxes & fees
17 Dec - 18 Dec
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

LAKEFRONT HIDDEN GEM !

LAKEFRONT HIDDEN GEM !
Elkhorn
9.6 out of 10, Exceptional, (35)
"Property was clean and the layout is absolutely beautiful."
United States
Daniel C.
LAKEFRONT HIDDEN GEM !

Stunning Upscale Retreat - Steps From Everything

Stunning Upscale Retreat - Steps From Everything
Lower East Side
9.8 out of 10, Exceptional, (31)
"It was a great place and close to Brady street! Definitely recommend. "
United States
Hugh L.
The price is NZ$923
includes taxes & fees
22 Dec - 23 Dec
Stunning Upscale Retreat - Steps From Everything

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Johnson Woods
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.
The price is NZ$558
includes taxes & fees
17 Dec - 18 Dec
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10

Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10
Burnham Park
9.6 out of 10, Exceptional, (253)
"This spacious house is a true gem, lovingly preserved. Really enjoyed our stay!!!!"
United States
Lynne W.
Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10

Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers
Bay View
9.6 out of 10, Exceptional, (8)
"Great place!"
United States
Kathy R.
The price is NZ$801
includes taxes & fees
23 Dec - 24 Dec
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Waukesha Hotel Reviews

Find out more about Waukesha

Everything you need to know about Waukesha 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 Waukesha holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Waukesha holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Waukesha holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Waukesha. 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 Waukesha 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 Waukesha holiday rentals we have selected for you start as low as NZ$278 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Waukesha rentals

At Expedia, we put the best Waukesha 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 Waukesha 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 Waukesha 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 Waukesha. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Waukesha?

Yes, there are holiday rentals in Waukesha close to Frame Park Formal Gardens, or you can select a more secluded option if you're looking for a relaxing stay. The shops and live music are just a few reasons why travellers like Waukesha. Make sure you have time to check out the architecture and sporting events during your trip.

What are some of the best holiday rentals that Waukesha has to offer?

7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!: This holiday home rental outside of Waukesha is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Waukesha?

Expedia has 5 holiday rentals for your stay in Waukesha.

What can I see and do in Waukesha?

Frame Park Formal Gardens and Infinity Fields Baseball Park are a couple of scenic spots to enjoy the outdoors, whereas Waukesha County Museum is one of the cultural attractions. While here, Center Court Sports Complex and Waukesha County Expo Center are other places worth a visit.

What are holiday rentals like in Waukesha?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Waukesha. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for family trips or small group gatherings.