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Vacation rentals in Greendale

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Top-rated vacation rentals in Greendale

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Rental unit in West Allis

4.96 out of 5 average rating, 131 reviews

Sunny State Fair Sojourn!

Newly renovated upper unit in a 1902 Victorian home. 2 bedroom, one bath, kitchen, dining area, living room, and office space! Less than one block from Wisconsin State Fair Park, The Milwaukee Mile and local bus routes! Minutes from American Family Field, Milwaukee County Zoo, and more! Local shuttle to Summerfest and other concerts and sporting events withing walking distance! Private balcony, free parking for one car, private laundry in the unit. Owner occupied lower for over 25 years!

Guest suite in Brookfield

5 out of 5 average rating, 209 reviews

In the Canopy (beautiful Brookfield/Milwaukee)

Relax “in the Canopy” of beautiful maples! If you’re looking for party central…this isn’t it. But if you want a comfortable place in a tree-filled neighborhood, just a few minutes from all the best Milwaukee has to offer, you’re in luck! Perfect location for quick access to the city—or to Lake Country to the west. Quiet, comfortable, safe, surrounded by beautiful gardens. We’re in a perfect launching spot to visit Summerfest, Brewers/Bucks games, or Milwaukee's western suburbs. Bring the kids!

Rental unit in Bay View

4.86 out of 5 average rating, 219 reviews

The LuLu Nest: Bay View Studio, 5 min to downtown!

Cozy and convenient studio apartment in the center of one of Milwaukee's hottest neighborhoods! Bay View, situated right betw downtown Milwaukee and the airport/Amtrak hub, is the perfect neighborhood to enjoy all the best Milwaukee has to offer. This studio apartment is only one of five in our building and is situated right above a popular neighborhood restaurant yet still quiet and tranquil enough for a good night's sleep. Book 5+ nights and receive a gift certificate to our restaurant!

Rental unit in Bay View

4.95 out of 5 average rating, 729 reviews

Beautiful Bay View MKE Flat - w/parking!

This is a bright, sunny apartment on the upper level of a sweet little 1870's "Polish Flat" in the heart of Bay View, one of the city's most desirable neighborhoods! We are just steps away from some of Milwaukee's best restaurants, bars, taprooms, boutiques and coffee shops. The space features an efficiency kitchenette, living room, beautiful bedroom and renovated bathroom with walk-in shower! Close to East Side, Walker’s Point, Historic Third Ward, Summerfest, Mitchell Park and the airport.

Townhouse in Bay View

4.95 out of 5 average rating, 388 reviews

Vintage Bay View - Big Backyard, Big 1 Bedroom

Welcome to your Milwaukee getaway! Located in the Bay View area, you're walking distance from the best farm-to-table restaurants, music venues, art fairs, and craft beer in the city. Not only that, but Lake Michigan's beaches, Miller Park, and downtown are a short drive away. The location is ideal. The place was created with a 70's midwestern feel, with wood-paneled furniture pieces and mod design. It also boasts a giant kitchen and backyard with grill. We can't wait for you to visit!

Home in Wauwatosa

4.98 out of 5 average rating, 202 reviews

Wauwatosa/Milwaukee “Inglewood Place”Best Location

Great location near all Milwaukee attractions. Cozy upper two bedroom duplex with keyless entry in quiet Tosa. Extras such as ironed sheets, snacks and personal items are included. Walk to popular bars and restaurants in the village and along North Ave. Full kitchen and new beds make this a home away from home. 10 min to Froedtert & The Medical College of WI & Children’s Hospital of WI. Near Am Fam Field (Brewers stadium) and the lakefront. 4 miles to downtown Milwaukee. COME STAY WITH U

Rental unit in Wauwatosa

4.98 out of 5 average rating, 324 reviews

Great Location, Wauwatosa (upper unit)

This bright & super clean upper (19 stairs) 2 bedroom duplex is in the heart of East Tosa. ( bel air cantina, cranky al's, rocket baby, rosebud theater, il mito, north ave. grill, camp bar and micro brewery within 1/2 a block to 4 blocks of this house) Centrally located for quick access to Medical College/Froedert, Miller park, Milwaukee County Zoo, Downtown, Harley Museum, Milwaukee Art Museum & Summerfest/lakefront festival grounds. 1 space off street parking. Bublr & bus stop nearby.

Guest suite in Sussex

4.96 out of 5 average rating, 276 reviews

The Loft @ The Butler Place. 1846 homestead.

The Loft at the Butler Place is a beautiful, quiet retreat set in the rural suburb of Sussex, just 30 minutes west of Milwaukee. The home is the 1846 homestead of the William Butler family, making the home older than the State of Wisconsin! The 2019 remodel of the Loft is in sophisticated farmhouse style and pays tribute to the history of the home in its furnishings, up cycled pieces, and beautiful setting. "Broken becomes blessed" both tells and compells as an invitation to all.

Home in West Allis

4.81 out of 5 average rating, 129 reviews

Designer Cottage with Parking, Patio & Netflix

LOCATION, LOCATION! • Fast Fiber Internet TIME (MIN) 5-10 McCarty Park (Water Park, Trails, B-Ball Court) STATE FAIR TOSA 10-15 Brewers, Bucks Harley, 3rd Ward Breweries, Zoo ATTN MEDICAL Near All Hospitals PRIVATE PATIO & FENCED-BACKYARD • Seating for 4 w/ table • 🐶 can roam • Safe & secure kids play • Space for games & bags SAFE PARKING • Allows 2-4 vehicles inc. trucks & boats • 100FT off street • driveway widens LAUNDRY • W&D • Pods & D-Sheets • Util. Sink • Iron+Board

Guest suite in Cudahy

4.92 out of 5 average rating, 103 reviews

RARE Private Butler’s Suite in Historic Home

Luxurious, Industrial, historical. Sherlock Holmes meets Restoration Hardware. Declared a historical landmark, the home was built in 1892 and owned by the architect who designed the township of Cudahy. It is one of the last remaining remnants of the era. The room itself was a former speakeasy during prohibition. 10 minutes from the airport. 12 minutes from downtown Milwaukee. A short walk to Lake Michigan and Sheridan Park. Plenty of coffee shops and restaurants around.

Rental unit in West Allis

4.91 out of 5 average rating, 297 reviews

The Cheese House

Large well appointed two bedroom, living room, dining room, kitchen, and private balcony. Apartment is located on the second floor right above the award winning West Allis Cheese & Sausage Shoppe. Each stay includes 4 breakfast sandwiches and house coffee vouchers for the cheese store cafe. The rental is centrally located minutes from Pettit National Ice Center, Milwaukee County Zoo, Wisconsin State Fair, and Brewers Stadium not to mention local restaurants.

Home in Greendale

4.95 out of 5 average rating, 111 reviews

The Robin's Roost LLC

Relax with the whole family at this peaceful place to stay. Located within walking distance to the Fabulous Rock Sports Complex. You can also enjoy Luxe Golf Bays, a high tech, 250 yd turf driving range with 57 bays equipped with Track management range technology. You can also dine here, or at the other 2 restaurants. You will be just 2 miles from, Historic Downtown Greendale, featuring unique shops, boutiques, restaurants and cafés.

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Popular amenities for Greendale vacation rentals

Free parking on premises

Air conditioning

Stay near Greendale's top sights

Boerner Botanical Gardens19 locals recommend

Southridge Mall15 locals recommend

Whitnall Park8 locals recommend

Ricardo's Pizza6 locals recommend

Vintage 385 locals recommend

Joey Gerard's - A Bartolotta Supper Club5 locals recommend

Other great vacation rentals in Greendale

Home in Cudahy

4.95 out of 5 average rating, 58 reviews

3BR Home in Milwaukee - near airport & downtown

Rental unit in South Milwaukee

5 out of 5 average rating, 36 reviews

Cozy private getaway, Hot Tub, Music theme

Rental unit in West Allis

4.85 out of 5 average rating, 27 reviews

The Wine House

Home in Milwaukee

5 out of 5 average rating, 28 reviews

Cozy Dog Friendly Home Near Airport & Downtown

Rental unit in West Allis

4.83 out of 5 average rating, 24 reviews

Apartment in West Allis!

Home in West Allis

4.94 out of 5 average rating, 34 reviews

The Stallis Palace

Home in West Allis

4.85 out of 5 average rating, 40 reviews

Green Valley Homes - Updated Lower Apartment

Home in Milwaukee

5 out of 5 average rating, 24 reviews

House in Alverno Neighborhood

Quick stats about vacation rentals in Greendale

Total rentals
20 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
730 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Frequently Asked Questions

Are there family-friendly vacation rentals in Greendale?
Greendale has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Greendale?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Greendale?
Yes! Work meets play with ease at over 10 vacation rentals in Greendale featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Greendale have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Greendale. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Greendale?
Four-legged friends are welcome in Greendale. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Greendale have wifi?
Absolutely! We offer over 20 house rentals with wifi in Greendale. Enjoy a tailored experience with all the comforts you desire.

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