Greendale holiday rentals

We found 719 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:25 Dec - 1 Jan

Interior
Outdoor dining
Dining
Exterior
Exceptional
(6 reviews)

Skyline House on the Hill - Downtown Milwaukee

Milwaukee

7% off
AU$10,552
for 7 nights, 1 home
AU$1,507 per night
includes taxes & fees
Skyline House on the Hill - Downtown Milwaukee
One of two bedrooms on main level, with two twin XL beds and closet.
Dining room has decorative fireplace, bar cart, and a variety of drinkware.
Dead Bird Brewery, only 3 blocks away — has vintage arcade games and vegan food.
Front living room seating with view to front yard.
Exceptional
(45 reviews)

Spacious house, yard, hot tub & games — 1 mile to Downtown and the East Side

Milwaukee

11% off
AU$8,056
for 7 nights, 1 home
AU$1,151 per night
includes taxes & fees
Spacious house, yard, hot tub & games — 1 mile to Downtown and the East Side
Room
Terrace/patio
Dining
Private kitchen
Exceptional
(8 reviews)

Brady St Retreat! 4BR House w Patio & Fenced Yard

Milwaukee

6% off
AU$4,176
for 7 nights, 1 home
AU$597 per night
includes taxes & fees
Brady St Retreat! 4BR House w Patio & Fenced Yard
Dining
Living area
Private kitchen
Living area
Exceptional
(27 reviews)

Oak Park Bliss: 3BR, 2BA Gem

Milwaukee

7% off
AU$6,596
for 7 nights, 1 home
AU$942 per night
includes taxes & fees
Oak Park Bliss: 3BR, 2BA Gem
Living area
Private kitchen
Room
Interior
Exceptional
(24 reviews)

Cottage near Mt. Mary College

Milwaukee

7% off
AU$3,534
for 7 nights, 1 cottage
AU$505 per night
includes taxes & fees
Cottage near Mt. Mary College
King Bed
Dining
Living area
Exterior
Exceptional
(17 reviews)

Whole House in Bay View + Fenced-in Yard + Parking

Milwaukee

12% off
AU$3,552
for 7 nights, 1 home
AU$507 per night
includes taxes & fees
Whole House in Bay View + Fenced-in Yard + Parking
Exterior
Living area
Dining
Interior
Exceptional
(26 reviews)

Green Valley Homes - 2 BDRM Lower Apartment

Milwaukee

7% off
AU$1,997
for 7 nights, 1 home
AU$285 per night
includes taxes & fees
Green Valley Homes - 2 BDRM Lower Apartment
Terrace/patio
Exterior
Living area
Private kitchen
Exceptional
(18 reviews)

Milwaukee Bayview Getaway with Private Hot Tub

Milwaukee

7% off
AU$6,185
for 7 nights, 1 home
AU$884 per night
includes taxes & fees
Milwaukee Bayview Getaway with Private Hot Tub
Living area
Exterior
Dining
Room
Exceptional
(34 reviews)

The Gem of Brewers Hill with hot tub and seasonal pool

Milwaukee

7% off
AU$3,229
for 7 nights, 1 home
AU$461 per night
includes taxes & fees
The Gem of Brewers Hill with hot tub and seasonal pool
Dining
Living area
Room
Private kitchen
Exceptional
(17 reviews)

Spacious house, 8 mins downtown Sleeps 8 guests. Backyard

Milwaukee

7% off
AU$4,073
for 7 nights, 1 home
AU$582 per night
includes taxes & fees
Spacious house, 8 mins downtown Sleeps 8 guests. Backyard
Interior
Interior
Dining
Private kitchen
Exceptional
(18 reviews)

Huge condo in historic hotel near Lake Michigan/Parks/Festivals w/parking

Milwaukee

7% off
AU$4,410
for 7 nights, 1 apartment
AU$630 per night
includes taxes & fees
Huge condo in historic hotel near Lake Michigan/Parks/Festivals w/parking
Room
Exterior
Private kitchen
Interior
Exceptional
(5 reviews)

Stylish Studio in Walkers Point

Milwaukee

11% off
AU$1,765
for 7 nights, 1 apartment
AU$252 per night
includes taxes & fees
Stylish Studio in Walkers Point
New Paint!!!
Twilight!!
NEW!! 7 person hot tub
Grand Entrance!!
Exceptional
(233 reviews)

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

Caledonia

7% off
AU$3,781
for 7 nights, 1 home
AU$540 per night
includes taxes & fees
7 1/2 Acre Estate, Awesome Farm House with Heated Pool, Hot tub, Fishing Pond
Living area
Terrace/patio
Room
Private kitchen
Exceptional
(17 reviews)

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

Milwaukee

7% off
AU$4,184
for 7 nights, 1 home
AU$598 per night
includes taxes & fees
Spacious 3BR/2BA Townhome w/ Private Parking & Walkable East Side
Cozy living room with leather sofa, wood floors, and stylish dark accents
Exterior
Cozy modern bedroom with luxe white bedding and warm designer touches
Cozy lounge corner beside a bright, stylish kitchen
Exceptional
(5 reviews)

Stylish Apt in Walker's Point

Milwaukee

12% off
AU$2,336
for 7 nights, 1 apartment
AU$334 per night
includes taxes & fees
Stylish Apt in Walker's Point
  • 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)
  • 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)
  • Pewaukee Lake Beach (16.8 mi / 27.1 km)
  • North Beach Park (17.7 mi / 28.4 km)
  • Pewaukee Lake (18.2 mi / 29.2 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 accomodation in Greendale?
In Greendale, holiday houses are the most popular type of holiday rental, with about 15 available throughout the area. These homes typically offer spacious layouts, making them great for families or groups. Most include fully equipped kitchens, comfortable living areas, and outdoor spaces such as patios or gardens for relaxing after a day of exploring. The residential neighbourhoods provide a peaceful atmosphere, allowing guests to enjoy the local charm while being close to nearby parks and community amenities.
Are there any family house rentals in Greendale?
In Greendale, Wisconsin, there are several family-friendly house rentals available, making it a suitable destination for those travelling with children. The neighbourhood offers a range of homes that typically feature spacious living areas, fully equipped kitchens for family meals, and outdoor spaces where kids can play safely. Many properties come with amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for all guests.Visitors can explore the nearby parks, including the picturesque Greendale Park, which boasts playgrounds and picnic areas, great for outdoor activities. The historic district of Greendale also provides a charming atmosphere with local shops and dining options that cater to families.
Are there pet-friendly house rentals in Greendale?
In Greendale, Wisconsin, there are several pet-friendly house rentals available, making it an excellent choice for travellers who wish to bring their furry companions along. Many of these homes cater to families and groups, often featuring amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas. Some properties even offer additional features like fenced yards or nearby walking paths, which are ideal for pet owners.The charming neighbourhood of Greendale itself has a lovely community feel, with access to local parks where pets can enjoy some fresh air and exercise. The nearby Greendale Park provides ample space for walking dogs and enjoying the outdoors.
Are there any remote work holiday rentals in Greendale?
In Greendale, Wisconsin, there are several remote work-friendly holiday rentals available, with around 15 options to choose from. Many of these properties are equipped with essential amenities for remote work, such as high-speed Wi-Fi, dedicated desk spaces, and comfortable chairs to ensure a productive environment.The area itself is a charming suburban community, offering a peaceful setting for those looking to balance work and leisure. Nearby parks and recreational areas provide opportunities for relaxation and outdoor activities during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Greendale?
In Greendale, popular rental amenities include fully equipped kitchens, ideal for preparing meals, along with blenders for those who enjoy smoothies or cooking. Many properties also feature air conditioning to ensure comfort during warmer months. Guests can expect outdoor spaces such as decks or patios, great for relaxing or enjoying a meal al fresco. Onsite parking is another convenient amenity, making it easier for visitors to explore the surrounding area.
When is the best time to visit Greendale for a holiday rental?
The peak season for visiting Greendale, Wisconsin, is from May to July, with July standing out as the most popular month. During this vibrant time, the community comes alive with various outdoor festivals, farmers' markets, and family-friendly events, making it an ideal period for travellers seeking a lively option and plenty of activities.The summer months offer warm temperatures, typically ranging from the mid-teens to low 30s Celsius, great for enjoying the beautiful parks and scenic trails that Greendale has to offer. Outdoor enthusiasts can appreciate leisurely strolls, picnics, and even biking along the picturesque paths, all while soaking in the beauty of the area.For those looking to stretch their budget a bit further, visiting in December can be a smart choice. It's cooler, with temperatures hovering around freezing, the charm of the holiday season transforms Greendale into a winter wonderland. You can enjoy festive decorations, local holiday events, and a quieter atmosphere, which can enhance the overall experience.Ultimately, the best time to visit Greendale for a holiday rental really depends on whether you prefer the energetic buzz of summer festivities or the cosy, peaceful vibe of winter celebrations.
What are the top attractions in Greendale?
In Greendale, visitors can enjoy a variety of attractions that highlight the charm of this historic village. The Greendale Historic District features beautifully preserved mid-century architecture and is great for leisurely strolls. The Greendale Public Library offers a welcoming space for reading and community events, making it a great spot for families.Nearby, the picturesque Greendale Park provides opportunities for outdoor activities such as picnicking and walking along well-maintained trails. For those interested in local history, the Greendale Village Hall and the surrounding area often host community events and festivals throughout the year.
Are all fees included in the Greendale holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Greendale holiday homes with parking?
Stayz offers a wide selection of holiday homes in Greendale with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Greendale holiday homes?
You can find great discounts on holiday homes in Greendale on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Greendale holiday home booking on Stayz?
To find Greendale holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Greendale?
A long-stay holiday home in Greendale is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Greendale holiday home?
Book your Greendale holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Greendale?
Prices for holiday homes in Greendale vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Greendale to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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