Greendale holiday rentals

We found 720 holiday rentals — enter your dates for availability
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:6 Nov - 13 Nov

Historic landmark Arts & Crafts home designed by Alexander C. Eschweiler
Massive living room with Roku-enabled TV, wi-fi, comfy furniture, cozy woodwork
Dining room with beautiful woodwork and antique upright piano
Landing looking down from 2nd floor
Exceptional
(8 reviews)

Huge Historic House Centrally Located in Milwaukee

Milwaukee

8% off
AU$3,740
for 7 nights, 1 home
AU$534 per night
includes taxes & fees
Huge Historic House Centrally Located in Milwaukee
Room
Private kitchen
Living area
Property grounds
Excellent
(5 reviews)

Quiet Retreat in Morgan Heights, Sleeps 6, 1.5 baths

Milwaukee

17% off
AU$2,043
for 7 nights, 1 home
AU$292 per night
includes taxes & fees
Quiet Retreat in Morgan Heights, Sleeps 6, 1.5 baths
Interior
Private kitchen
Room
Living area
Exceptional
(22 reviews)

Cottage near Mt. Mary College

Milwaukee

7% off
AU$2,652
for 7 nights, 1 cottage
AU$379 per night
includes taxes & fees
Cottage near Mt. Mary College
Exterior
Living area
Dining
Interior
Exceptional
(23 reviews)

Green Valley Homes - 2 BDRM Lower Apartment

Milwaukee

7% off
AU$1,687
for 7 nights, 1 home
AU$241 per night
includes taxes & fees
Green Valley Homes - 2 BDRM Lower Apartment
Room
Living area
Living area
Dining
Exceptional
(25 reviews)

Oak Park Bliss: 3BR, 2BA Gem

Milwaukee

8% off
AU$4,923
for 7 nights, 1 home
AU$703 per night
includes taxes & fees
Oak Park Bliss: 3BR, 2BA Gem
Dining
Living area
Private kitchen
Exterior
Exceptional
(5 reviews)

Tosa Village Bungalow: Cozy, Charming, Walk to Tosa Village, Parks, and Stores

Milwaukee

7% off
AU$3,465
for 7 nights, 1 home
AU$495 per night
includes taxes & fees
Tosa Village Bungalow: Cozy, Charming, Walk to Tosa Village, Parks, and Stores
Kitchen
Dining table
Backyard and parking space
Living room's tv
Exceptional
(70 reviews)

Eastside apartment with Private entrance and parking

Milwaukee

15% off
AU$1,367
for 7 nights, 1 apartment
AU$195 per night
includes taxes & fees
Eastside apartment with Private entrance and parking
Room
Private kitchen
Exterior detail
Dining
Exceptional
(41 reviews)

3 BR-2Q 2T Beds, 1 bath home walk to State Fair, close to Brewers, & Zoo.

Milwaukee

10% off
AU$1,639
for 7 nights, 1 home
AU$234 per night
includes taxes & fees
3 BR-2Q 2T Beds, 1 bath home walk to State Fair, close to Brewers, & Zoo.
New Paint!!!
Twilight!!
NEW!! 7 person hot tub
Dining Area
Exceptional
(227 reviews)

7 1/2 Acre Estate, Awesome Farm House with Heated Pool, Hot tub, Fishing Pond

Caledonia

7% off
AU$3,732
for 7 nights, 1 home
AU$533 per night
includes taxes & fees
7 1/2 Acre Estate, Awesome Farm House with Heated Pool, Hot tub, Fishing Pond
Room
Terrace/patio
Interior
Private kitchen
Exceptional
(16 reviews)

Spacious 3BR/2BA Townhome w/ Private Parking & Walkable East Side

Milwaukee

7% off
AU$4,101
for 7 nights, 1 home
AU$586 per night
includes taxes & fees
Spacious 3BR/2BA Townhome w/ Private Parking & Walkable East Side
Dining
Exterior
Living area
Private kitchen
Exceptional
(18 reviews)

Milwaukee Bayview Getaway with Private Hot Tub

Milwaukee

7% off
AU$6,105
for 7 nights, 1 home
AU$872 per night
includes taxes & fees
Milwaukee Bayview Getaway with Private Hot Tub
  • 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, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Greendale

  • Rich Cultural Tapestry: Immerse in history with local museums and heritage sites that narrate Greendale’s fascinating past.
  • Family-Friendly Fun: Enjoy engaging attractions such as fairgrounds and transport museums, ideal for all ages.
  • Scenic Outdoor Escapes: Revel in picturesque parks and serene trails perfect for leisurely strolls.
  • Charming Neighbourhoods: Explore vibrant local shops and welcoming community spaces.
  • Modern & Historic Blend: Experience a unique fusion of city sophistication and historical charm in Greendale.

Popular types of accommodation in Greendale

Welcome to Greendale, Wisconsin, a charming city known for its picturesque parks and vibrant community spirit. Explore the delightful local shops, enjoy serene walks along the scenic trails, or immerse yourself in the rich history at the local heritage sites. With a variety of accommodation options, including private holiday homes, apartments, and cottages, you’ll find the perfect place to unwind after a day of adventure in this lovely Midwestern gem.

  • Private Holiday Homes: These spacious residences are the most sought-after option, offering a homely atmosphere for families and groups.
  • Apartments: Ideal for couples or solo travellers, these compact living spaces provide comfort and convenience in a more urban setting.
  • Cottages: Quaint and charming, these rustic getaways are perfect for those seeking a peaceful retreat in nature.
  • Cabins: Often nestled in wooded areas, these cosy lodgings provide a unique experience close to the great outdoors.
  • Condos: These modern units offer a blend of luxury and practicality, often featuring communal amenities for guests.**

Top attractions near Greendale

Greendale, Wisconsin offers a delightful mix of family-friendly attractions and outdoor experiences. Visitors can explore the local fairground showground, transport museum, and history museum, all of which provide a rich cultural journey. Whether you’re travelling with family or seeking an engaging city escape, Greendale’s unique blend of history and modernity caters to every taste, ensuring a memorable visit in this charming American locale.

  • Harley-Davidson Museum: Discover the rich history of this iconic motorcycle brand at the Harley-Davidson Museum. With engaging exhibits showcasing vintage bikes and memorabilia, it's a delightful experience for families and culture enthusiasts alike.
  • Lakeshore State Park: Enjoy the scenic beauty of Lakeshore State Park, an urban oasis perfect for outdoor activities. With picturesque views of the city skyline, it's a family-friendly spot for picnics, walking, and biking along the waterfront.
  • Pebble Beach: Relax at Pebble Beach, a charming sandy retreat ideal for sunbathing and leisurely strolls. The beach vibes create a perfect atmosphere for unwinding and enjoying the natural surroundings.

Things to do recommended for couples

Embark on a romantic escapade in Greendale. Venture 11km away to Sky Safari, a cable car gondola offering an outdoor, adventurous experience perfect for couples in love. Relish the charm of local delights and create lasting memories together.

Things to do recommended for families

Families in Greendale can explore local parks and museums, sample delicious local treats, and enjoy scenic walks. There are plenty of kid-friendly activities to ensure a delightful experience for every family member.

Things to do recommended for groups

Groups visiting Greendale can experience the thrill of motor racing at Milwaukee Mile Speedway, just 10km away, or embark on an exhilarating adventure at the Sky Trail zipline ropes course, located 11km from the town, perfect for outdoor enthusiasts.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Greendale

If you're travelling with a group, family, pets, or planning for an extended stay, it's important to apply the appropriate filters to suit your needs. Here are some helpful booking tips for your Stayz experience.

  • Traveling to Greendale with a group: Consider how many bedrooms you'll require, along with features like a fully-equipped kitchen or an outdoor area for group gatherings. Fortunately, you can refine your search for all these options and more on Stayz.
  • Traveling to Greendale with young kids: Traveling with young children can be demanding. You must prioritise their comfort and safety, along with considering age-appropriate amenities like a private swimming pool. It’s also advisable to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Greendale: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, we invite you to explore Stayz properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Greendale: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Greendale

Greendale offers a delightful experience for family and business travellers. Explore charming local attractions, scenic neighbourhoods, and inviting outdoor spaces within walking distance. Enjoy leisurely strolls through the city’s backyard areas and immerse yourself in the warm, friendly atmosphere of Milwaukee County. Greendale’s blend of city sophistication and family-friendly vibes makes it a perfect base for a memorable holiday visit.

  • Milwaukee: Milwaukee is a vibrant metropolis situated nearby Greendale, celebrated for its rich cultural scene and diverse outdoor activities. Visitors flock to this city for family outings, romantic escapades, and thrilling adventures. Key attractions include major sports stadiums, event venues, and scenic lakeside areas. Milwaukee's lively music concerts and theatrical performances add to its charm, ensuring there's always something happening. With its blend of urban excitement and natural beauty, Milwaukee provides an engaging travel experience for all types of tourists.
  • Greenfield: Just 3km from Greendale, Greenfield is a welcoming neighbourhood ideal for family-friendly excursions and business-related visits. The area boasts numerous shopping centres and malls, perfect for indulging in retail therapy. Visitors can also enjoy local fairs and community events. Greenfield’s proximity to event venues and sports facilities enhances its appeal, making it a convenient spot for both leisure and work. The friendly atmosphere and range of amenities contribute to a pleasant experience for those exploring this charming community.
  • Hales Corners: Located 5km from Greendale, Hales Corners is a delightful city that offers a mix of outdoor activities and family-friendly attractions. Visitors are drawn to its enchanting botanical garden and expansive urban parks, ideal for leisurely strolls or picnics. The area hosts music concerts and various fairground events, ensuring fun for all ages. With its community-focused vibe and beautiful green spaces, Hales Corners is a perfect destination for those looking to immerse themselves in a vibrant city atmosphere while enjoying nature.

Best time to go to Greendale

If you're planning a trip to Greendale, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like February, October and December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January22.1°F (-5.5°C)Light RainMostly CloudyAverageSlightly Low
February23.7°F (-4.6°C)Light RainMostly CloudySlightly LowSlightly Low
March35.1°F (1.7°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageAverage
May55.4°F (13.0°C)Light RainMostly SunnyAverageAverage
June65.7°F (18.7°C)Light RainMostly SunnySlightly HighSlightly High
July71.8°F (22.1°C)Light RainMostly SunnySlightly HighSlightly High
August70.9°F (21.6°C)Light RainMostly SunnyAverageSlightly High
September64.4°F (18.0°C)Light RainMostly SunnySlightly HighAverage
October52.0°F (11.1°C)Light RainMostly SunnySlightly LowAverage
November39.4°F (4.1°C)Light RainMostly SunnyAverageAverage
December29.8°F (-1.2°C)Light RainMostly CloudySlightly LowAverage

Booking with Stayz is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can lead to significant savings, as prices tend to vary. Additionally, opting for a longer stay often results in considerable discounts. To discover the perfect Stayz property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz's Trip Board offers a user-friendly platform for you to organise your travel plans, whether you're starting a new journey, resuming an existing one, or simply reviewing your arrangements. You can easily find your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

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 Speedway (5.6 mi / 9 km)
  • Milwaukee County Zoo (6.7 mi / 10.8 km)
  • Henry W. Maier Festival Park (7.9 mi / 12.7 km)
  • Springs Water Park (16 mi / 25.8 km)
  • Crystal Ridge (1.6 mi / 2.5 km)
  • Milwaukee County Sport Complex (4.7 mi / 7.6 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)
  • Bradford Beach (10.4 mi / 16.7 km)
  • Quarry Lake Park (15.9 mi / 25.6 km)
  • Pewaukee Lake Beach (16.8 mi / 27.1 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 home accommodation in Greendale?
According to our data, houses are the most sought-after type of holiday home in Greendale. But having said that, everyone's idea of an epic stay will differ. Stayz 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 home in Greendale?
A number of factors determine the price of a holiday home 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 home 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 Stayz 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 homes in Greendale?
You're in luck. There are. You can choose from three holiday homes that welcome pets in Greendale on Stayz. Our furry best friends need a getaway too, so simply use our search function for pet-friendly holiday homes to find a property where Rover can join in the fun.
What are popular home amenities in Greendale?
A garden, nearby museums and a nearby casino are the most popular home amenities in Greendale. Whether you're taking to the road solo, with your other half or a bunch of friends, Stayz can help you find a holiday home that fits your style with all the extras you're looking for.
Are there large group holiday homes 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 homes in Greendale that welcome kids?
With three family-friendly holiday homes 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 homes with air conditioning in Greendale?
Select your dates and then make use of our filters to look for holiday homes with ac in Greendale on Stayz. 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 home in Greendale?
The minimum required age is generally 16, 18 or 21. It can change from one property to another on Stayz, so check the rules of your chosen Greendale holiday home before booking your trip.
How long can I rent a holiday home in Greendale for?
The length of time you can book a holiday home 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.

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