Book Holiday Homes in Greendale
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Greendale
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
Waukesha WI
The price is AU$465 per night from 4 Jan to 5 Jan
AU$465
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at this vacation home in Waukesha, you'll be within a 5-minute drive of Monkey Joe's and Prairieville Park.
Family Paradise 3 bedroom, Cozy Home + Game Room.
Brown Deer WI
With a stay at this vacation home in Milwaukee (Brown Deer), you'll be within a 10-minute drive of Lake Michigan and Walter Schroeder Aquatic Center.
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Milwaukee WI
The price is AU$715 per night from 23 Dec to 24 Dec
AU$715
23 Dec - 24 Dec
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Milwaukee, within a 5-minute drive of Lake Michigan and Fiserv Forum.
Save an average of 15% on thousands of hotels when you're signed in
Charming Vintage Farmhouse 1 bedroom Garden Oasis
Milwaukee WI
With a stay at this vacation home in Milwaukee (Bay View), you'll be a 1-minute drive from Lake Michigan and 8 minutes from Fiserv Forum.
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18
New Berlin WI
The price is AU$4,362 per night from 15 Jan to 16 Jan
AU$4,362
15 Jan - 16 Jan 2026
includes taxes & fees
With a stay at this vacation home in New Berlin, you'll be within a 10-minute drive of Waukesha Springs Park and Minooka Park.
Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!
River Hills WI
With a stay at this vacation home in Milwaukee, you'll be within a 15-minute drive of Lake Michigan and Fiserv Forum.
Remodeled Home - Steps from Brady Street!
Milwaukee WI
The price is AU$412 per night from 12 Jan to 13 Jan
AU$412
12 Jan - 13 Jan 2026
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Milwaukee, within a 5-minute drive of Lake Michigan and Fiserv Forum.
Brady St Retreat! 4BR House w Patio & Fenced Yard
Milwaukee WI
With a stay at this vacation home in Milwaukee (Lower East Side), you'll be within a 5-minute drive of Lake Michigan and Fiserv Forum.
Serene 4-bedroom Lake House in Pewaukee-Hot Tub!
Pewaukee WI
With a stay at this vacation home in Pewaukee (Starke Peninsula), you'll be a 1-minute drive from Pewaukee Lake and 5 minutes from Two Brothers Wines.
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.
Greendale Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Greendale vacation homes are the perfect way for you to wing it.
Holiday houses in Greendale let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Greendale in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Greendale adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Greendale with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Greendale vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Greendale Holiday Homes essential information
Accommodation | 474 Holiday Homes |
|---|---|
Lowest Price | AU$228 |
Highest Price | AU$4,362 |
Popular accommodation | Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub, Family Paradise 3 bedroom, Cozy Home + Game Room., Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find, Charming Vintage Farmhouse 1 bedroom Garden Oasis, 17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18, Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!, Remodeled Home - Steps from Brady Street!, Brady St Retreat! 4BR House w Patio & Fenced Yard, Serene 4-bedroom Lake House in Pewaukee-Hot Tub! |
Top trending hotels in Greendale
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is AU$271 per night from 13 Jan to 14 Jan
AU$271
13 Jan - 14 Jan 2026
includes taxes & fees
With a stay at The Pfister Hotel, you'll be centrally located in Milwaukee, within a 5-minute drive of Lake Michigan and Fiserv Forum.
Saint Kate - The Arts Hotel
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is AU$228 per night from 28 Dec to 29 Dec
AU$228
28 Dec - 29 Dec
includes taxes & fees
With a stay at Saint Kate - The Arts Hotel, you'll be centrally located in Milwaukee, within a 10-minute walk of Riverside Theater and Fiserv Forum.
Potawatomi Hotel & Casino
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is AU$249 per night from 5 Jan to 6 Jan
AU$249
5 Jan - 6 Jan 2026
includes taxes & fees
With a stay at Potawatomi Hotel & Casino in Milwaukee (Menomonee River Valley), you'll be steps from Marquette University and a 2-minute drive from Harley-Davidson ...
Save an average of 15% on thousands of hotels when you're signed in
The Iron Horse Hotel
500 W Florida Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is AU$255 per night from 5 Jan to 6 Jan
AU$255
5 Jan - 6 Jan 2026
includes taxes & fees
With a stay at The Iron Horse Hotel, you'll be centrally located in Milwaukee, within a 5-minute drive of Harley-Davidson Museum and Fiserv Forum.
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.
More ways to explore Greendale
Top picks
Hotels
- Lakes Entrance Beach Hotels
- Accommodation in Central Coast
- Accommodation in Bangkok
- Gold Coast Pet Friendly Hotels
- Hotels in Caloundra
- Le Meridien Khao Lak Resort & Spa
- Accommodation in Melbourne
- Accommodation in Australia
- Accommodation in Nowra
- Hotels in South Brisbane
- Hotels near Heathrow
- Sydney Harbour Marriott Hotel at Circular Quay
- Hotels around Liverpool Hospital
- Hotels in Taylors Lakes
- Accommodation in Tokyo
- Hotels around Taronga Western Plains Zoo
- Accommodation in Dubbo
- Accommodation in Port Lincoln
- Hotels in Dunsborough
- Hotels in Maudsland
- Armidale Spa Hotels
- Hanoi E Central Hotel
- Manly Apartment Hotels
- Broadbeach Hotels with Parking
- Accommodation in Wollongong
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.