Waukesha Holiday Rentals

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Holiday Rentals in Waukesha

Beautiful Waukesha Home
10.0 out of 10, Exceptional, (6)
"We stayed here to attend my daughter's graduation from Graduate School, and it was the perfect location. The house was beautiful, and clean with plenty of room for our family. Would highly recommend."
The price is NZ$890
per night
19 Jun - 20 Jun
Beautiful Waukesha Home
The Plaza Hotel
3.0 star property
8.6 out of 10, Excellent, (986)
"The place was very clean, friendly staff and well kept up. It has a lot fo its original historic charm which I really liked."
The price is NZ$316
per night
30 Jun - 1 Jul
The Plaza Hotel
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events Allowed! Read Description
9.8 out of 10, Exceptional, (181)
"This is the second time we stayed at The Retreat. LOTS of space inside and out for our family to gather. Kids age 3-10 could not get enough of the heated pool and the adults especially enjoyed the hot tub. We added an 'exrra' and had a small family reunion one of the afternoons and the place was perfect for this. Game room such a bonus when it rained. We didn't need to leave the property but some checked out 7 Mile Fair. Communication with the owner was timely. I'm sure the family will vote to...
The price is NZ$1,532
per night
30 Jun - 1 Jul
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events Allowed! Read Description
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Amazing Five Bedroom Milwaukee Vacation Home!!
10.0 out of 10, Exceptional, (30)
"Huge pool and pool room, arcade, pool table, ping pong, what’s not to like…?"
Amazing Five Bedroom Milwaukee Vacation Home!!
Kasa Westown Milwaukee
4.0 star property
9.0 out of 10, Wonderful, (44)
"Great location close to downtown "
The price is NZ$323
per night
17 Jun - 18 Jun
Kasa Westown Milwaukee
Family Retreat, private, large, great for multi-family, company retreat, wedding
10.0 out of 10, Exceptional, (46)
"This property is fantastic! Great amenities, clean, huge open spaces, and comfortable beds! The owners/property managers were great, too!"
Family Retreat, private, large, great for multi-family, company retreat, wedding
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna
9.6 out of 10, Exceptional, (5)
"Hosted 20 employees at this house for 2nd year in a row. Never disappoints! Fantastic property. Indoor pool and sauna a bonus. Fit everyone comfortably. Host was very easy to work with. Perfect stay! We will be back next Spring."
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River
9.8 out of 10, Exceptional, (300)
"Had a wonderful time, couldn’t ask for a better location and host. Will recommend to all my friends! Thanks again Grant!"
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River
10min to DT + Fire Pit + Home Gym + Shuffleboard
10.0 out of 10, Exceptional, (7)
"We were in MKE for an extended family gathering and this home was perfect for our party of six. Clean, well maintained, with everything we needed to feel comfortable. Good communication with hosts. We will stay here again when visiting the area. Highly recommend."
The price is NZ$808
per night
3 Jun - 4 Jun
10min to DT + Fire Pit + Home Gym + Shuffleboard
SuMMeR IS HeRe BrinG ur boat and tie to dock, Tavern, huge DECK, KIDS jungle gym
9.0 out of 10, Wonderful, (8)
"This is a great location, remote and quiet, just what we wanted. Our family reunion was a big success! No WiFi was an issue for people who needed to make contact with work issues, and of course kids were not happy about it, but sometimes it’s nice to disconnect. However cell phone reception was limited so getting directions was challenging at times. All said and done we had a wonderful time and wouldn’t hesitate to go back and do it again."
SuMMeR IS HeRe BrinG ur boat and tie to dock, Tavern, huge DECK, KIDS jungle gym
Eclectic, Stylish, and Cozy Milwaukee Unit!
10.0 out of 10, Exceptional, (4)
"Fantastic location for night life. Spacious home for our family"
The price is NZ$549
per night
4 Jun - 5 Jun
Eclectic, Stylish, and Cozy Milwaukee Unit!
Historic House, Frank Lloyd Wright-Designed House In Milwaukee, WI
9.8 out of 10, Exceptional, (219)
"I have ALWAYS wanted to stay in a Frank Lloyd Wright house! What a gorgeous home! Joan was very accommodating. We were there for a family wedding. Close to airport, close to downtown. Loved it."
Historic House, Frank Lloyd Wright-Designed House In Milwaukee, WI
Urban Oasis minutes to Fiserv, Summerfest & more
9.8 out of 10, Exceptional, (8)
"This rental is gorgeous and spacious. The host was great with communication. Great stay."
The price is NZ$384
per night
3 Jun - 4 Jun
Urban Oasis minutes to Fiserv, Summerfest & more
3000 sq ft home - Private 25 acres on a river - 45 min from Milwaukee or Madison
10.0 out of 10, Exceptional, (6)
"Lovely house and grounds. All rules were clear and communication was succinct. We had a lovely time with our families. Thanks to Jennifer"
The price is NZ$1,424
per night
5 Jun - 6 Jun
3000 sq ft home - Private 25 acres on a river - 45 min from Milwaukee or Madison
15 minutes to anywhere in and around Milwaukee.
10.0 out of 10, Exceptional, (14)
"Very clean and cozy. Perfect for two or three people. It is a basement apartment but nice windows so it doesn't feel totally under ground. The hosts live upstairs and are very nice! Nice area outside if you want to hang out outdoors. I will definitely stay here again."
The price is NZ$269
per night
4 Jun - 5 Jun
15 minutes to anywhere in and around Milwaukee.
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!
10.0 out of 10, Exceptional, (3)
"We loved this property! Five of us stayed for the night and had everything we needed! The apartment is spacious, has a large variety of sleeping options and is extremely clean. The decor looks exactly like the photos (even better in person!) and has all the amenities you will need, including a washer and dryer if need be. Check in was simple and seamless. The neighborhood was clean and felt very safe. The host is wonderful. She communicates quickly and was able to answer all of our questions. We...
The price is NZ$818
per night
2 Jun - 3 Jun
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!
Booth Upper · Amazing view, Modern Space
10.0 out of 10, Exceptional, (26)
"Awesome area to have a fun time in MKE without need for vehicle"
Booth Upper · Amazing view, Modern Space
Cozy 5-Bedroom Home in Milwaukee
10.0 out of 10, Exceptional, (1)
"Very clean. Very spacious. Great location. Only issue only one bathroom. If you’re okay with that it’s a perfect place. A lot of space and many food options in walking distance close to the airport."
The price is NZ$617
per night
30 Jun - 1 Jul
Cozy 5-Bedroom Home in Milwaukee
Nice three 3 bedroom unit with free parking and wi-fi
7.2 out of 10, Good, (12)
"The place was clean but old. Not enough dishes, toilet paper, no paper towels. There was wash cloths and towels but they were put up very high we didn’t find them until it was time to leave but over all it was a great place to lay our heads and we thank the owner My recommendation is to paint and update unit to look bright and sleek and to get a toilet for tall people. My mom had a hard time sitting on the low toilet so did I. Overall it served it’s purpose"
The price is NZ$330
per night
30 Jun - 1 Jul
Nice three 3 bedroom unit with free parking and wi-fi
Safe location lively Wauwatosa and within 10 min of what Milwaukee has to offer.
10.0 out of 10, Exceptional, (14)
"Nice area. House did what it needed to"
The price is NZ$647
per night
4 Jun - 5 Jun
Safe location lively Wauwatosa and within 10 min of what Milwaukee has to offer.
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See all available properties in Waukesha
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.

Other types of properties in Waukesha you may be interested in

Extended Stay America Suites Milwaukee Waukesha
2.5 star property
7.2 out of 10, Good, (710)
"It was nice. Only complaint is lack of availability of eating utensils for eating and cooking area."
The price is NZ$141
per night
31 May - 1 Jun
Extended Stay America Suites Milwaukee Waukesha
Tru By Hilton Milwaukee Brookfield
2.5 star property
8.8 out of 10, Excellent, (535)
"Definitely a good experience my first time staying on this hotel but everyone was super friendly "
The price is NZ$177
per night
11 Jun - 12 Jun
Tru By Hilton Milwaukee Brookfield
Saint Kate - The Arts Hotel
4.0 star property
9.8 out of 10, Exceptional, (1686)
"Everything was top tier!"
The price is NZ$336
per night
2 Jun - 3 Jun
Saint Kate - The Arts Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Waukesha holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Waukesha. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Waukesha. Seeing all the best attractions is bound to make you fall in love with Waukesha. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Waukesha short-term rentals, that won’t be hard to do.

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?

Step right up, step right up! Welcome to the grand, the unique, the unparalleled: This holiday home rental outside of Waukesha is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade/games room.

How many holiday rentals are there in Waukesha?

Expedia has 4 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.

Recent reviews of Waukesha properties
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