Greendale holiday lettings

We found 792 holiday rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

August 2025

September 2025

Discover a selection of 5 homes and other holiday rentals in Greendale that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, which might include Wi-Fi and a pool. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Greendale

Showing deals for:14 Nov - 21 Nov

Exceptional

(6 reviews)

W172-Lannon · Charming Muskego House, Walk to Lake & Restaurants

Muskego, WI

12% off

£169 per night

includes taxes & fees

Welcome to the Pink Door Place. Feel at home in this cozy, chill spot!

Exceptional

(6 reviews)

Pink Door Place with fenced yard in a walkable area & 2 miles from Fiserv Forum

Milwaukee, WI

8% off

£151 per night

includes taxes & fees

Very good

(9 reviews)

JUST REMODELED Cozy, quiet,BrewersStadium Walk Distance. ClosetoDownTown,SteFair

Milwaukee, WI

7% off

£239 per night

includes taxes & fees

Exceptional

(14 reviews)

4 bd Victorian, close to downtown, great for groups and family gatherings

Milwaukee, WI

7% off

£440 per night

includes taxes & fees

Exceptional

(22 reviews)

Historic Greendale Original within short walking distance of the quaint village

Greendale, WI

15% off

£78 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Greendale

Enjoy a stay in Greendale, WI a National Historic Landmark!

Sleeps 5 · 3 bedrooms · 1+ bathroom

Historic home - walk to village center. Original features with modern updates.

Sleeps 6 · 3 bedrooms · 1+ bathroom

Historic Greendale Original within short walking distance of the quaint village

Sleeps 2 · 1 bedroom · 1 bathroom

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Find out more about Greendale

Book a holiday rental for your Greendale getaway

Learn about the unique charm of Greendale with a stay in a holiday home rental. One of the city's many top draws is its restaurants. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Greendale

Are you searching for attractions to see during your stay? Venture out of your cosy holiday rental and experience everything that Greendale has to offer. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

Milwaukee Mile (5.5 mi / 8.9 km)
Milwaukee County Zoo (6.7 mi / 10.8 km)
Henry W. Maier Festival Park (7.9 mi / 12.7 km)
Ray's MTB Indoor Mountain Bike Park (15.8 mi / 25.5 km)
Springs Water Park (16 mi / 25.8 km)
Crystal Ridge (1.6 mi / 2.5 km)

Exploring the natural features in Greendale

Whether you're an active traveller or just want to spend some time taking in the scenery, Greendale is a great place to spend some time outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

Boerner Botanical Gardens (1.8 mi / 2.8 km)
Mitchell Park Horticultural Conservatory (6.4 mi / 10.3 km)
Veteran's Park (8.7 mi / 13.9 km)
Riverwalk Plaza (8.7 mi / 14 km)
Bradford Beach (10.4 mi / 16.7 km)
Atwater Park & Beach (12 mi / 19.4 km)

Transport options to and around Greendale

The nearest airport is in Milwaukee, WI (MKE-General Mitchell Intl.), located 4.8 mi (7.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Waukesha, WI (UES-Waukesha County), which is 14 mi (22.5 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Greendale?

According to our data, houses are the most sought-after type of holiday rental in Greendale. But having said that, everyone's idea of an epic stay will differ. Vrbo has holiday homes with every shape, size and budget in mind, so you're bound to find the perfect match.

How much does it cost to rent a holiday rental in Greendale?

A number of factors determine the price of a holiday rental in Greendale, including the season, type of property and length of stay. However, all our holiday homes have one thing in common — exceptional value. Just enter your travel dates to find your ideal match.

How much does it cost to rent a beach house in Greendale?

The average price for a holiday rental by the beach in Greendale will depend on when you're going and the style and size of property you want. Find prices easily on Vrbo by entering your preferred travel dates and destination. Then use the filter tool to pick the number of bedrooms and amenities that you need, like air conditioning, WiFi and a pool.

Are there pet-friendly holiday rentals in Greendale?

You're in luck. There are. You can choose from three holiday homes that welcome pets in Greendale on Vrbo. Our furry best friends need a getaway too, so simply use our search function for pet-friendly holiday rentals to find a property where Rover can join in the fun.

What are popular rental amenities in Greendale?

A garden, nearby museums and a nearby casino are the most popular rental amenities in Greendale. Whether you're taking to the road solo, with your other half or a bunch of friends, Vrbo can help you find a holiday home that fits your style with all the extras you're looking for.

Are there large group holiday rentals in Greendale?

Yes, you can choose one of two properties in Greendale that can accommodate a group of five or more guests. From family trips to events like a friend's birthday, these stays have ample room to kick back with the people that matter the most.

Are there holiday rentals in Greendale that welcome kids?

With three family-friendly holiday rentals to choose from in Greendale, now is an awesome time to introduce the little ones to the excitement of travel. Simply check our "Properties good for families" filter box to locate stays that come with conveniences perfect for families on the move, such as kitchens, pools, entertainment areas and hot tubs.

What are the top attractions for families in Greendale?

You'll find lots of wonderful things to do and see with the family in Greendale, such as:

Harley-Davidson Museum
Milwaukee County Zoo
Milwaukee Public Museum

How can I find holiday rentals with air conditioning in Greendale?

Select your dates and then make use of our filters to look for holiday rentals with ac in Greendale on Vrbo. With three air-conditioned properties to choose from here, you can look forward to a cool and comfortable break.

How old do you have to be to rent a holiday rental in Greendale?

The minimum required age is generally 16, 18 or 21. It can change from one property to another on Vrbo, so check the rules of your chosen Greendale holiday rental before booking your trip.

How long can I rent a holiday rental in Greendale for?

The length of time you can book a holiday rental in Greendale differs according to the property. Simply enter your preferred travel dates to look at a list of options offering extended stays. With tons of amenities such as air conditioning and laundries, as well as some offering discounted weekly or monthly prices, you're sure to find somewhere perfect to call your home away from home in Greendale.