Holiday Rentals in Greendale

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Our top choices for Greendale holiday rentals

Aparthotel in Downtown Milwaukee

The Plaza Hotel
3.0 star property
8.8 out of 10, Excellent, (1153)
"Loved this hotel! Clean friendly and cute!!"
United States
Sharon H
The price is €144
includes taxes & fees
4 Jan - 5 Jan 2026
The Plaza Hotel

Aparthotel in Westown

Kasa Westown Milwaukee
4.0 star property
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

Apartment in Westown

ROVE LIVING/KL - Malt House
4.0 star property
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 €139
includes taxes & fees
15 Dec - 16 Dec
ROVE LIVING/KL - Malt House
9.8 out of 10, Exceptional, (213)
"It was nice "
United States
Kevin C.
The price is €567
includes taxes & fees
21 Dec - 22 Dec
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!
7.8 out of 10, Good, (10)
"We had an excellent family vacation at The Garden of Eden!!"
United States
Cheryl S.
The price is €1,764
includes taxes & fees
15 Dec - 16 Dec
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

Apartment in Lower East Side

ROVE LIVING/KB - Prospect
3.0 star property
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
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

Holiday Home in Riverwest

Three bedrooms upstairs
9.6 out of 10, Exceptional, (78)
"He was very kind!"
United States
Hope
The price is €278
includes taxes & fees
11 Jan - 12 Jan 2026
Three bedrooms upstairs
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 €287
includes taxes & fees
15 Dec - 16 Dec
Downtown Eastside gem near Fiserv Forum Water St Brady St
9.6 out of 10, Exceptional, (66)
"It was clean and close to our wedding venue. "
United States
Kathy H.
The price is €370
includes taxes & fees
15 Dec - 16 Dec
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

Apartment in Downtown Milwaukee

Renovated Brady St. Classic
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
2.0 star property
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 €367
includes taxes & fees
16 Dec - 17 Dec
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
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 €467
includes taxes & fees
15 Dec - 16 Dec
Stunning Upscale Retreat - Steps From Everything
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 €288
includes taxes & fees
15 Dec - 16 Dec
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
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

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 €214
includes taxes & fees
15 Dec - 16 Dec
Wisconsin Treehouse Getaway!
9.6 out of 10, Exceptional, (8)
"Great place!"
United States
Kathy R.
The price is €452
includes taxes & fees
11 Jan - 12 Jan 2026
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers
9.8 out of 10, Exceptional, (366)
"Beautiful place, loved the fenced in yard for my Yorkies, very excited to stay there again!!"
United States
Pamela Q.
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

Holiday Home in Downtown Milwaukee

MKE Mansion - Both Wings
9.6 out of 10, Exceptional, (23)
"Great house - big group I stayed with loved it and tons of places to sleep and hang out. Fantastic location by the water and near some good restaurants. Hosts were super responsive. "
United States
Henri E.
MKE Mansion - Both Wings
9.8 out of 10, Exceptional, (17)
"Will come and stay again great host and home"
United States
Dion S.
The price is €264
includes taxes & fees
16 Dec - 17 Dec
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
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, apart-hotels, 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 €139 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?

7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!: This holiday home rental outside of Greendale 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 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.