Greendale holiday homes

We found 718 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:18 Dec - 25 Dec

Dining
Outdoor dining
Interior
Exterior
Exceptional
(6 reviews)

Skyline House on the Hill - Downtown Milwaukee

Milwaukee

7% off
NZ$13,503
for 7 nights, 1 home
NZ$1,929 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.
Neighborhood coffee roaster 4 blocks away. Try an award-winning Nitro cold brew.
Dead Bird Brewery, only 3 blocks away — has vintage arcade games and vegan food.
Exceptional
(45 reviews)

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

Milwaukee

11% off
NZ$10,043
for 7 nights, 1 home
NZ$1,435 per night
includes taxes & fees
Spacious house, yard, hot tub & games — 1 mile to Downtown and the East Side
Dining
Terrace/patio
Living area
Private kitchen
Exceptional
(7 reviews)

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

Milwaukee

6% off
NZ$4,943
for 7 nights, 1 home
NZ$706 per night
includes taxes & fees
Brady St Retreat! 4BR House w Patio & Fenced Yard
Living area
Living area
Room
Private kitchen
Exceptional
(27 reviews)

Oak Park Bliss: 3BR, 2BA Gem

Milwaukee

7% off
NZ$7,051
for 7 nights, 1 home
NZ$1,007 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
NZ$3,801
for 7 nights, 1 cottage
NZ$543 per night
includes taxes & fees
Cottage near Mt. Mary College
Exterior
Dining
Living area
King Bed
Exceptional
(17 reviews)

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

Milwaukee

12% off
NZ$3,662
for 7 nights, 1 home
NZ$523 per night
includes taxes & fees
Whole House in Bay View + Fenced-in Yard + Parking
Exterior
Living area
Private kitchen
Interior
Exceptional
(26 reviews)

Green Valley Homes - 2 BDRM Lower Apartment

Milwaukee

7% off
NZ$2,102
for 7 nights, 1 home
NZ$300 per night
includes taxes & fees
Green Valley Homes - 2 BDRM Lower Apartment
Terrace/patio
Exterior
Dining
Living area
Exceptional
(18 reviews)

Milwaukee Bayview Getaway with Private Hot Tub

Milwaukee

7% off
NZ$7,641
for 7 nights, 1 home
NZ$1,092 per night
includes taxes & fees
Milwaukee Bayview Getaway with Private Hot Tub
Room
Exterior
Living area
Dining
Exceptional
(34 reviews)

The Gem of Brewers Hill with hot tub and seasonal pool

Milwaukee

8% off
NZ$3,747
for 7 nights, 1 home
NZ$535 per night
includes taxes & fees
The Gem of Brewers Hill with hot tub and seasonal pool
Room
Living area
Dining
Exterior
Exceptional
(17 reviews)

Spacious house, 8 mins downtown Sleeps 8 guests. Backyard

Milwaukee

7% off
NZ$4,832
for 7 nights, 1 home
NZ$690 per night
includes taxes & fees
Spacious house, 8 mins downtown Sleeps 8 guests. Backyard
Private kitchen
Interior
Interior
Dining
Exceptional
(18 reviews)

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

Milwaukee

7% off
NZ$4,859
for 7 nights, 1 apartment
NZ$694 per night
includes taxes & fees
Huge condo in historic hotel near Lake Michigan/Parks/Festivals w/parking
Interior
Exterior
Room
Private kitchen
Exceptional
(5 reviews)

Stylish Studio in Walkers Point

Milwaukee

11% off
NZ$1,950
for 7 nights, 1 apartment
NZ$279 per night
includes taxes & fees
Stylish Studio in Walkers Point
Grand Entrance!!
Twilight!!
New Paint!!!
Dining Area
Exceptional
(232 reviews)

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

Caledonia

7% off
NZ$4,716
for 7 nights, 1 home
NZ$674 per night
includes taxes & fees
7 1/2 Acre Estate, Awesome Farm House with Heated Pool, Hot tub, Fishing Pond
Private kitchen
Terrace/patio
Interior
Room
Exceptional
(17 reviews)

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

Milwaukee

7% off
NZ$4,921
for 7 nights, 1 home
NZ$703 per night
includes taxes & fees
Spacious 3BR/2BA Townhome w/ Private Parking & Walkable East Side
  • Peace of mind

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  • More quality time

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  • 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

  • Charming historic district: Stroll through Greendale’s quaint streets filled with unique shops and local history.
  • Community theatre: Catch a show at the Greendale Community Theatre for a taste of local performing arts.
  • Scenic parks: Enjoy outdoor adventures in the beautiful parks, perfect for picnics and family outings.
  • Veterans Memorial: Pay tribute at the Greendale Veterans Memorial, adding to the town's rich cultural tapestry.
  • Welcoming locals: Experience the warm atmosphere and friendly locals that make Greendale special.

Top attractions near Greendale

Greendale, Wisconsin, offers a delightful mix of outdoor adventures and family-friendly activities. You can explore the historic district, catch a show at the Greendale Community Theatre, or enjoy a stroll through the charming village. Don't miss the Greendale Veterans Memorial and the local high school, which add to the area's rich cultural tapestry. Whether you're after romance or a family outing, Greendale has something for everyone.

  • Harley-Davidson Museum: Immerse yourself in the rich heritage of this iconic motorcycle brand. The museum showcases an impressive collection of bikes and memorabilia, offering a unique glimpse into American culture and innovation. Family-friendly activities make it a great spot for all ages.
  • Baird Center: This modern event and conference venue is perfect for business gatherings and corporate events. Its professional atmosphere provides state-of-the-art facilities, making it a hub for networking and collaboration.
  • Wisconsin State Fair Park: A vibrant fairground that hosts various events and exhibitions throughout the year. Enjoy outdoor activities, delicious food, and family-friendly entertainment in a lively atmosphere.

Things to do recommended for couples

Planning a romantic getaway in Greendale? Catch a live show at The Rave-Eagles Club for a lively night out, hit the slopes at Rock Snow Park for some fun on the snow, or enjoy a round at Moorland Road Golf Center for a bit of friendly competition.

Things to do recommended for families

For a fun family getaway in Greendale, visit American Family Field for a thrilling sports vibe, explore The Rock Sports Complex for wellness and relaxation, or enjoy ice skating at Pettit National Ice Center for an adventurous day out. Each offers a unique experience for everyone.

Things to do recommended for groups

Groups visiting Greendale can explore the vibrant Milwaukee Public Market for local bites, enjoy a romantic tour at Miller Brewery for a taste of craft beer, and experience the thrill of racing at Milwaukee Mile for an adrenaline-packed day out.

*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, or pets, or if you're considering longer stays, be sure to set your priorities when filtering your options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Greendale with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group get-togethers. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Greendale with young kids: Travelling with young kids can be quite a task. It's important to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Greendale: For many families, a holiday just wouldn't be the same without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of the family feels 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 spot. By using the appropriate filters, you can quickly locate and save on monthly accommodations. Don’t forget to think about including features like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay in Greendale

Greendale, Wisconsin, offers a delightful blend of outdoor adventures and family-friendly activities, making it a perfect spot for all types of vacations. Explore the charming neighbourhoods and enjoy the warm atmosphere filled with friendly locals. Just a short trip away, you can discover nearby cities that enhance your experience with romantic settings and vibrant excursions. With lovely weather and scenic spots, Greendale is sure to create lasting memories during your holiday.

  • Walker’s Point: Situated approximately 11.3km from Greendale, Walker’s Point is a vibrant neighbourhood that offers a delightful blend of family-friendly and romantic experiences. Known for its lively atmosphere, visitors can enjoy music concerts and theatrical performances, making it a cultural hub. The area is also home to significant landmarks like event conference venues and sports facilities, perfect for those who enjoy outdoor activities. Strolling through Walker’s Point, you’ll find charming spots for dining and entertainment, ensuring a memorable outing.
  • Milwaukee: As a bustling metropolis, Milwaukee is seamlessly integrated with Greendale, providing an extensive array of outdoor, family, and romantic activities. Just a stone’s throw away, visitors can immerse themselves in the city's rich cultural scene, from music concerts to engaging theatre performances. Renowned local attractions include the expansive lakefront and sports facilities, which are perfect for a day of exploration. Milwaukee’s vibrant atmosphere and diverse offerings make it a must-visit destination for any traveller.
  • Greenfield: Located a mere 3.2km from Greendale, Greenfield is a charming village that beckons families and sports enthusiasts alike. The area is known for its fairgrounds and theatre, which often host exciting events and shows, providing ample opportunities for family fun. Greenfield’s local attractions, including stadiums and event venues, create a lively community atmosphere. With a focus on outdoor experiences, this village offers a delightful escape for those looking to enjoy sports and recreational activities.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.1°F (-5.5°C)Light RainMostly CloudyAverage
February23.7°F (-4.6°C)Light RainMostly CloudySlightly Low
March35.1°F (1.7°C)Light RainMostly CloudyAverage
April44.2°F (6.8°C)Light RainMostly CloudyAverage
May55.4°F (13.0°C)Light RainMostly SunnyAverage
June65.7°F (18.7°C)Light RainMostly SunnySlightly High
July71.8°F (22.1°C)Light RainMostly SunnySlightly High
August70.9°F (21.6°C)Light RainMostly SunnyAverage
September64.4°F (18.0°C)Light RainMostly SunnySlightly High
October52.0°F (11.1°C)Light RainMostly SunnySlightly Low
November39.4°F (4.1°C)Light RainMostly SunnyAverage
December29.8°F (-1.2°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is a breeze

Want to make the most of your travel budget? It’s worth considering some flexibility with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient space for you to plan new adventures, revisit your existing arrangements, or organize your bookings. The properties you’ve saved or booked are now neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply head to: https://www.bookabach.co.nz/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)
  • Bradford Beach (10.4 mi / 16.7 km)
  • Pewaukee Lake Beach (16.8 mi / 27.1 km)
  • North Beach Park (17.7 mi / 28.4 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 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 Bookabach.
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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Greendale holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Greendale to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach 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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