Book Holiday Homes in Greendale

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Featured Holiday Homes in Greendale

Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

Waterford
Located in Waterford, this vacation home is on the waterfront, within a 15-minute drive of Jean Jacobson Dog Park and Green Meadows Petting Farm.
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

Milwaukee
The price is AU$814 per night from 7 Nov to 8 Nov
AU$814
includes taxes & fees
7 Nov - 8 Nov
With a stay at this vacation home, you'll be centrally located in Milwaukee, within a 5-minute drive of Lake Michigan and University of Wisconsin-Milwaukee.
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!
Amazing Five Bedroom Milwaukee Vacation Home!!

Amazing Five Bedroom Milwaukee Vacation Home!!

Sussex
Located in Sussex, this vacation home is within a 10-minute drive of Town Hall Clinic and Froedtert Menomonee Falls Hospital.
Amazing Five Bedroom Milwaukee Vacation Home!!
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Booth Upper · Amazing view, Modern Space

Booth Upper · Amazing view, Modern Space

Milwaukee
With a stay at this vacation home in Milwaukee (Riverwest), you'll be within a 5-minute drive of Fiserv Forum and Marquette University.
Booth Upper · Amazing view, Modern Space
Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan

Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan

Waterford
Located in Waterford, this vacation home is on the waterfront, within a 15-minute drive of Edgewood Golf Course and Jean Jacobson Dog Park.
Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

2 out of 5
Milwaukee
The price is AU$689 per night from 11 Nov to 12 Nov
AU$689
includes taxes & fees
11 Nov - 12 Nov
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.
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
Beautiful Waukesha Home

Beautiful Waukesha Home

Waukesha
The price is AU$840 per night from 6 Nov to 7 Nov
AU$840
includes taxes & fees
6 Nov - 7 Nov
A stay at this vacation home places you in the heart of Waukesha, a 5-minute drive from Glacial Drumlin Bike Trail and 5 minutes from Waukesha County ...
Beautiful Waukesha Home
Large, Private 3 Br Home | Ideal Location

Large, Private 3 Br Home | Ideal Location

Milwaukee
The price is AU$609 per night from 29 Nov to 30 Nov
AU$609
includes taxes & fees
29 Nov - 30 Nov
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.
Large, Private 3 Br Home | Ideal Location
Tichigan Lake House - Pontoon Boat & Fire Pit - Dog Friendly - Newly Renovated

Tichigan Lake House - Pontoon Boat & Fire Pit - Dog Friendly - Newly Renovated

Waterford
The price is AU$541 per night from 6 Nov to 7 Nov
AU$541
includes taxes & fees
6 Nov - 7 Nov
When you stay at this vacation home in Waterford, you'll be 13 minutes by car from Edgewood Golf Course.
Tichigan Lake House - Pontoon Boat & Fire Pit - Dog Friendly - Newly Renovated
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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
395 Holiday Homes
Lowest Price
AU$170
Highest Price
AU$840
Popular accommodation
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River, Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities! , Amazing Five Bedroom Milwaukee Vacation Home!!, Booth Upper · Amazing view, Modern Space, Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan, NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms, Beautiful Waukesha Home, Large, Private 3 Br Home | Ideal Location, Tichigan Lake House - Pontoon Boat & Fire Pit - Dog Friendly - Newly Renovated

Top trending hotels in Greendale

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is AU$231 per night from 26 Nov to 27 Nov
AU$231
includes taxes & fees
26 Nov - 27 Nov
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.
Saint Kate - The Arts Hotel
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is AU$265 per night from 2 Dec to 3 Dec
AU$265
includes taxes & fees
2 Dec - 3 Dec
A stay at The Pfister Hotel places you in the heart of Milwaukee, within a 15-minute walk of Lake Michigan and Milwaukee Art Museum.
The Pfister Hotel
Hilton Milwaukee City Center

Hilton Milwaukee City Center

4 out of 5
509 W Wisconsin Ave, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is AU$174 per night from 24 Nov to 25 Nov
AU$174
includes taxes & fees
24 Nov - 25 Nov
With a stay at Hilton Milwaukee City Center, you'll be centrally located in Milwaukee, just a 3-minute walk from Marquette University and 10 minutes by foot ...
Hilton Milwaukee City Center
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Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

4 out of 5
333 W Kilbourn Ave, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is AU$170 per night from 12 Nov to 13 Nov
AU$170
includes taxes & fees
12 Nov - 13 Nov
With a stay at Hyatt Regency Milwaukee, you'll be centrally located in Milwaukee, within a 10-minute walk of Fiserv Forum and Milwaukee Public Museum.
Hyatt Regency Milwaukee
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See all available properties in Greendale
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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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^Subject to availability and chosen travel dates.