Greendale Holiday Rentals

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Our top choices for Greendale holiday rentals

9.8 out of 10, Exceptional, (48)
"Great location and wonderful house. Great location for family with small kids. Parks are super close, downtown street is wonderful to eat and drink. Host is super helpful and responsive. "
United States
Patrick J.
The price is AU$515
includes taxes & fees
11 Jan - 12 Jan 2026
Historic home - walk to village center. Original features with modern updates.

Apartment in Racine

Welcome To My Loft!
10.0 out of 10, Exceptional, (16)
"Great place to stay!"
United States
kathleen
The price is AU$168
includes taxes & fees
4 Jan - 5 Jan 2026
Welcome To My Loft!

Apartment in Downtown Milwaukee

Downtown Luxury 2BR Penthouse Apt
2.0 star property
10.0 out of 10, Exceptional, (6)
"What an awesome location, we’ll definitely be back. The place was perfect!"
United States
Justin G.
The price is AU$238
includes taxes & fees
5 Jan - 6 Jan 2026
Downtown Luxury 2BR Penthouse Apt

Apartment in Murray Hill

2BR apt w/ laundry + parking
10.0 out of 10, Exceptional, (12)
"The apartment is clean, spacious and close to the activities we were in town for."
United States
Kelly S.
The price is AU$226
includes taxes & fees
5 Jan - 6 Jan 2026
2BR apt w/ laundry + parking
2.0 star property
8.0 out of 10, Very good, (3)
"Enjoyed the stay here very much! Host was very quick with communication as well. Would highly recommend !"
United States
Younique T.
Modern Studio by Brady St & Milwaukee Lakefront
10.0 out of 10, Exceptional, (2)
"Room was spotless and had great amenities. Great location. "
United States
Philip
The price is AU$182
includes taxes & fees
4 Jan - 5 Jan 2026
Deer District Studio Apt - One Block from Fiserv and Baird

Apartment in Downtown Milwaukee

Eclectic, Stylish, and Cozy Milwaukee Unit!
2.0 star property
9.8 out of 10, Exceptional, (39)
"Great property! We would definitely recommend it and stay again. "
United States
Bridget M.
The price is AU$485
includes taxes & fees
8 Jan - 9 Jan 2026
Eclectic, Stylish, and Cozy Milwaukee Unit!
2.0 star property
9.4 out of 10, Exceptional, (14)
"Check-in and parking were easy. Kitchen was well stocked and included some spices. Location was perfect to catch some Brewers games. Beds were comfortable. Will stay again!"
United States
Debra D.
Comfort Near Historic Pabst Brewery & Fiserv
10.0 out of 10, Exceptional, (1)
"We enjoyed our stay at East Side Luxury apartments. Everything was as advertised and it was great staying close to Brady St. We would definitely stay here again."
United States
Greg W.
The price is AU$188
includes taxes & fees
5 Jan - 6 Jan 2026
East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge
10.0 out of 10, Exceptional, (7)
"Charming apartment, convenient location"
United States
Ashton G.
The price is AU$303
includes taxes & fees
14 Jan - 15 Jan 2026
KK lower · Funky 2BR in Prime Bay View - w/ Parking
10.0 out of 10, Exceptional, (1)
"Great location to the concert and lots to do around the area. Safe place and area"
United States
Timothy S.
The price is AU$222
includes taxes & fees
4 Jan - 5 Jan 2026
Cream City 2BR Apt - Just 3 Blocks to Fiserv with Gym and Parking

Holiday Home in Downtown Milwaukee

Remodeled Home - Steps from Brady Street!
10.0 out of 10, Exceptional, (5)
"Enjoyed stay at this nice home "
United States
Eduardo P.
The price is AU$394
includes taxes & fees
5 Jan - 6 Jan 2026
Remodeled Home - Steps from Brady Street!
9.4 out of 10, Exceptional, (3)
"Host was amazing and answered all questions. Location is great and walking distance to the night life. "
United States
Jacob D.
The price is AU$214
includes taxes & fees
12 Jan - 13 Jan 2026
Modern Studio Apt with Skywalk to Fiserv, Rooftop, and Parking
10.0 out of 10, Exceptional, (6)
"Nice place "
United States
John B.
The price is AU$278
includes taxes & fees
21 Jan - 22 Jan 2026
Potter Upper · Bright 1.5BR in the Heart of Bay View - w/ Parking
8.4 out of 10, Very good, (7)
"Our host was great with communication and we enjoyed the stay at this unique property and appreciated the history behind the building and how it has been preserved in a modern industrial style! "
United States
Maria Doxtator
The price is AU$232
includes taxes & fees
1 Jan - 2 Jan 2026
Brewery District 2-Story 2BR Apt Near Fiserv with Rooftop, Gym, and Parking
9.8 out of 10, Exceptional, (8)
"Great place in a cool area! Highly recommend. "
United States
Maggie B.
The price is AU$255
includes taxes & fees
6 Jan - 7 Jan 2026
Close to MU & Fiserv | Gym, W/D & Parking
10.0 out of 10, Exceptional, (16)
"Everything was as advertised. Very nice area of Wawatosa. "
United States
seeton p.
The price is AU$386
includes taxes & fees
11 Jan - 12 Jan 2026
King Bed - Near Froedtert - FAST WiFi
10.0 out of 10, Exceptional, (35)
"It was comfortable and affordable. Nice location walking distance to a lot of venues "
United States
Bill M.
The price is AU$501
includes taxes & fees
6 Jan - 7 Jan 2026
Charming home w/ fire pit, walk to Lake Michigan

Apartment in Racine

Wisconsin Treehouse Getaway!
9.6 out of 10, Exceptional, (26)
"We had a wonderful time staying here while visiting the surrounding area!"
United States
Collin C.
The price is AU$370
includes taxes & fees
1 Jan - 2 Jan 2026
Wisconsin Treehouse Getaway!

Holiday Home in Milwaukee

Quiet House
7.2 out of 10, Good, (7)
"Great stay for attending Summerfest. Short trip to the festival. Place was tidy and comfortable."
United States
Kerry N.
The price is AU$292
includes taxes & fees
4 Jan - 5 Jan 2026
Quiet House
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 Greendale Hotel Reviews

Find out more about Greendale

Everything you need to know about Greendale 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 Greendale 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 Greendale holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Greendale holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greendale. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greendale 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 Greendale holiday rentals we have selected for you start as low as AU$246 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Greendale rentals

At Expedia, we put the best Greendale 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 Greendale 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 Greendale 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 Greendale. 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 Greendale?

Yes, there are holiday rentals close to the most popular sights in Greendale, or you can select a more secluded option if you're looking for a relaxing stay. Greendale is known for its restaurants.

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

Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find: This holiday home rental outside of Greendale is located on the beach, and has a fireplace, a patio 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. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals will I find in Greendale?

Expedia has 5 holiday rentals for your stay in Greendale.

What’s there to see and do in Greendale?

While exploring the area, visit family-friendly sights like Crystal Ridge, or get outside and enjoy nature at Boerner Botanical Gardens. In the wider area, you’ll find Rock Snow Park and The Rock Sports Complex.

What’s a holiday rental in Greendale like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Greendale. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a family trip or a small group gathering.