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 NZ$583
includes taxes & fees
4 Jan - 5 Jan 2026
Historic home - walk to village center. Original features with modern updates.

Aparthotel in Downtown Milwaukee

The Plaza Hotel
3.0 star property
8.8 out of 10, Excellent, (1153)
"From check in to check out excellent stay!"
United States
Heather
The price is NZ$282
includes taxes & fees
18 Jan - 19 Jan 2026
The Plaza Hotel
10.0 out of 10, Exceptional, (2)
"Room was spotless and had great amenities. Great location. "
United States
Philip
The price is NZ$205
includes taxes & fees
4 Jan - 5 Jan 2026
Deer District Studio Apt - One Block from Fiserv and Baird

Aparthotel in Westown

Kasa Westown Milwaukee
4.0 star property
9.0 out of 10, Wonderful, (121)
"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
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 NZ$212
includes taxes & fees
4 Jan - 5 Jan 2026
East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge

Apartment in Downtown Milwaukee

Downtown Luxury 1BR Loft
8.8 out of 10, Excellent, (3)
"Recently rehab. Very nice finishes. Safe, quiet, and walkable to many restaurants. "
United States
Brandon
The price is NZ$246
includes taxes & fees
30 Dec - 31 Dec
Downtown Luxury 1BR Loft
10.0 out of 10, Exceptional, (5)
"Great room "
United States
julio
The price is NZ$242
includes taxes & fees
30 Dec - 31 Dec
Modern Studio Apt with Skywalk to Fiserv, Rooftop, 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 NZ$455
includes taxes & fees
30 Dec - 31 Dec
Remodeled Home - Steps from Brady Street!
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.
The price is NZ$295
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Near Historic Pabst Brewery & Fiserv

Apartment in Fifth Ward

Stylish Apt in Walker's Point
10.0 out of 10, Exceptional, (4)
"I loved my stay here! the location is in a good area near downtown milwaukee with lots of food near by! My stay here was great and the host was very responsive and helpful and provided lots of information. Very cute and aesthetic decor, felt very homey! "
United States
Anthony R.
Stylish Apt in Walker's Point

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 NZ$256
includes taxes & fees
5 Jan - 6 Jan 2026
2BR apt w/ laundry + parking
10.0 out of 10, Exceptional, (6)
"Nice place "
United States
John B.
The price is NZ$284
includes taxes & fees
14 Jan - 15 Jan 2026
Potter Upper · Bright 1.5BR in the Heart of Bay View - w/ Parking

Apartment in Racine

Welcome To My Loft!
10.0 out of 10, Exceptional, (16)
"Great place to stay!"
United States
kathleen
The price is NZ$190
includes taxes & fees
31 Dec - 1 Jan 2026
Welcome To My Loft!
9.4 out of 10, Exceptional, (6)
"Great location! Super-cool historic building. Easy booking and check-in process, and responsive host. We will be back!"
United States
Christy M.
The price is NZ$261
includes taxes & fees
1 Jan - 2 Jan 2026
Brewery District Luxe 2BR Near Fiserv with Parking
7.8 out of 10, Good, (6)
"It was really nice ,only issue was trying to watch tv, but other than that was good , i would stay there again "
United States
Marty E.
The price is NZ$251
includes taxes & fees
4 Jan - 5 Jan 2026
Cream City 2BR Apt - Just 3 Blocks to Fiserv with Gym and Parking
10.0 out of 10, Exceptional, (7)
"Charming apartment, convenient location"
United States
Ashton G.
The price is NZ$339
includes taxes & fees
13 Jan - 14 Jan 2026
KK lower · Funky 2BR in Prime Bay View - w/ Parking

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 NZ$582
includes taxes & fees
11 Jan - 12 Jan 2026
Eclectic, Stylish, and Cozy Milwaukee Unit!
2.0 star property
8.4 out of 10, Very good, (7)
"Great location and cozy apartment"
United States
Javier O.
The price is NZ$231
includes taxes & fees
4 Jan - 5 Jan 2026
Chic MKE Studio | Walk to Beach & Brady St Dining
2.0 star property
10.0 out of 10, Exceptional, (1)
"Five stars all the way!"
United States
Rob K.
The price is NZ$514
includes taxes & fees
4 Jan - 5 Jan 2026
Historic Walker’s Point Home, Garage & Yard
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 favorite 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 depends 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 NZ$282 per night. Entering your travel dates in the search wizard you might find 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.