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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Guest favourite
A modern kitchen showcases sleek stainless steel appliances, including a refrigerator and oven. White cabinetry complements the light countertops. A small dining table with two chairs is positioned near a window, providing natural light to the space. Tasteful artwork adorns the walls.
Guesthouse in Franklin
4.84 out of 5 average rating, 38 reviews

The Crows Nest Cottage 1

Welcome to our charming 1-bedroom cottage by a serene pond. This cozy retreat features a unique basketball/pickleball court, multiple outdoor patios, and a delightful treehouse lounge area. Perfect for relaxation ! Just 5 minutes away is The Rock Sports Complex, offering top-tier activities like Topgolf, minor league baseball, an umbrella bar, hiking trails,ski hills.Whether you’re seeking tranquility or adventure, our cottage provides the ideal getaway for both.washer,dryer BOAT TOURS AVAILABLE

Superhost
A modern living area features rich wooden beams overhead and soft seating arrangements. A sleek television is positioned on a media console, with a decorative plant adding a touch of greenery. Natural light filters through sheer curtains, creating a bright and inviting space.
Home in Greendale
4.74 out of 5 average rating, 88 reviews

Designer Home in Walkable Historic Greendale

Extended Stays Welcome! Situated in an ideal walkable location, the Villager on Arrowwood is an absolute gem in the heart of the historic Village of Greendale. Updated with a modern style and mid century touches. Work from the office which includes a fold-out couch. Enjoy dual outdoor spaces with the front screened porch and large backyard with patio. Just steps from Village's inviting downtown shops and restaurants - the perfect place to experience the unique charm and history of Greendale!

Guest favourite
The exterior of a two-story house is depicted, characterized by white walls and dark trim. A bench is positioned on the front porch, and trees with autumn leaves frame the scene. Sunlight highlights the structure, creating a warm yet neutral ambiance.
Home in Greendale
4.95 out of 5 average rating, 40 reviews

Cozy, historic home in walkable Greendale village

Your family will be close to everything when you stay at this centrally-located, original but renovated 3 bedroom/1.5 bath in the Historic Village of Greendale. Enjoy a stroll through the walkways connecting various parks, shopping and dining on just a few blocks away on Broad Street. You'll love the friendly village vibe. Just an easy 15 minute drive from downtown/lakefront, if you are in the mood for a city vibe. We hope you enjoy this cozy home and the village of Greendale as much as we do!

Guest favourite
A cozy living room is highlighted by a light gray sofa adorned with decorative cushions. A small blue coffee table sits in front, complemented by a candle and a framed picture. Natural light enters through a window, brightening the neutral-colored walls.
Home in West Allis
4.79 out of 5 average rating, 190 reviews

★Cozy Beach Themed Home★2 Beds★Spacious Parking★

Cozy and quaint two bedroom beach themed home located in the heart of West Allis. Close to public transportation and a few minutes driving to State Fair Park, Milwaukee County Zoo, Potawatomi Hotel & Casino, bars, restaurants, and more! Peaceful and quiet residential spot with plenty of parking on premises (up to 3 cars.) Amenities include: Spacious Parking, Smart TV, WiFi, Self Check in, Fresh Sheets & Towels, Hairdryer, Fully Stocked Kitchen, Washer & Dryer, Reading Material and much more!

Top guest favourite
Apartment in Milwaukee
4.98 out of 5 average rating, 54 reviews

Mid-Century Modern Apartment

This stylish and spacious apartment provides the perfect stay. Experience convenience and comfort in this freshly updated one-bedroom apartment. Centrally located, with easy access to many attractions & amenities. The property is well located within 5 minutes from multiple freeway interchanges. Downtown Milwaukee is a quick 15 minute commute, while the American Family Field is a mere 10 minutes away. Apartment is situated on the second floor of a 3-unit building. Dedicated workspace provided.

Top guest favourite
The exterior of a vintage two-story home in a sunlit setting is shown, featuring a soft yellow façade and green window trims. A white picket fence outlines a landscaped area, while mature trees provide shade along the walkway leading to the entrance.
Home in Greendale
5 out of 5 average rating, 74 reviews

A Showplace of Greendale History on Apple Court

This entire 3 bedroom home is a vintage gem in Historic Greendale, Wisconsin — and it's all yours! • NO extra charge for cleaning! • FREE on-site parking for two cars • An EASY walk to charming boutiques & eateries • Located in a National Historic Landmark district • Steeped in 1930s History with Eleanor Roosevelt design features Features stylish, functional layout as part of FDR’s 1930s New Deal. Includes high speed Internet, central air conditioning, private patio for outdoor enjoyment.

Top guest favourite
A spacious living area features a comfortable sofa with colorful throw pillows, paired with a light coffee table on a soft rug. Large windows allow natural light to fill the room, complemented by stylish curtains, while a kitchen area is seen in the background.
Apartment in Milwaukee
4.99 out of 5 average rating, 86 reviews

Stylish 3-bd place with back yard & free parking

Comfortable 3 bedroom lower unit in a duplex, with fenced in back yard and patio. Make our apartment your home-away-from-home, while visiting Milwaukee for either business or leisure. Its three bedrooms comfortably sleep six people. Fully equipped kitchen encourages in-home cooking. There is onsite laundry and two free parking spaces . We are close to hospitals, downtown with its professional buildings, shopping, restaurants and parks. Perfect home for long-term temporary work assignments.

Guest favourite
A spacious living area features a blue sectional sofa and a yellow accent chair, offering an inviting seating arrangement. A brown coffee table sits on a patterned rug, while large windows allow for natural light. A desk with a chair is positioned nearby for work or leisure.
Home in West Allis
4.87 out of 5 average rating, 126 reviews

West Allis Oasis

Welcome to our cozy 2-bedroom, 1-bathroom home on a quiet street in a fantastic neighborhood. Dog-friendly and perfect for families or solo travelers, enjoy easy access to I-94 and the State Fair Park just a few blocks away. Our home offers a peaceful retreat with comfortable furnishings, a fully equipped kitchen, cozy bedrooms, and large fenced in yard. Relax and unwind in a tranquil environment after a day of exploring. Book your stay today for the perfect blend of comfort and convenience!

Superhost
Place to stay in Racine
4.85 out of 5 average rating, 808 reviews

Wisconsin Treehouse Getaway!

Featured in Timeout Magazine as Chicago's Top 10 Airbnbs, and in other outlets as Wisconsin's most romantic and top 5 Airbnbs, this space has an immersive nature experience, overlooking a creek and woods with all modern comforts. Imagine yourself in a cabin in the woods to unplug and recharge, waking up to chirping birds as if in a Treehouse! 3 miles to Lake Michigan & dwntn. lf we're home, a complimentary Chai! Come, make lifelong memories at Racine's Best Kept Secret No local bookings.

Guest favourite
A single-story ranch-style home is presented, featuring a well-maintained exterior with a light-colored stone façade. Green grass surrounds the property, complemented by neatly trimmed bushes and a paved walkway leading to the front door. The roof is covered with gray shingles under a partly cloudy sky.
Home in Wauwatosa
4.92 out of 5 average rating, 114 reviews

Relax close to everything in Milwaukee

Ranch Style home in a quiet Neighborhood. You will feel at home and comfortable! The home is well maintained and very clean. In the winters you could cozy up to a nice fire upstairs and relax with a glass of wine. Downstairs is a second fireplace you have going and play a game of pool. In The summer you can enjoy the three seasons room, with looking a cup of coffee and look at the planted flower garden. Close to the Wauwatosa village down town. Even closer to Elm Grove Village.

Guest favourite
A spacious living room features a dark blue couch and a wooden coffee table on a decorative area rug. A flat-screen TV stands on a media console, displaying various streaming options. Light enters through large windows adorned with curtain panels, while a wall clock is mounted above.
Townhouse in Greenfield
4.82 out of 5 average rating, 62 reviews

Spacious 3-Bedroom Townhouse

Enjoy your stay in this spacious house located just 15 minutes away from downtown Milwaukee and Summerfest, and 10 minutes away from State Fair. Including the peaceful neighborhood, you'll be within walking distance of various restaurants and shops. Within the home, you'll find a comfortable experience lounging in any of the 3 bedrooms, playing outside in the expansive yard, or relaxing in the sunroom. Provided are a 52" TV, washing and drying machine, and 570 Mbps wifi.

Superhost
The studio features hardwood floors and exposed wooden beams adding character. A spacious bed is centrally positioned, accompanied by soft bedding. A small dining table and kitchenette with essential appliances are visible. A modern light fixture provides illumination near a cozy reading chair.
Apartment in West Allis
4.8 out of 5 average rating, 328 reviews

Kegel's Inn - Studio - Classic Apartment #3

Quaint little studio with lots of old-world character. This one-room studio has original hardwood floors, heavy wood ceiling beams and 1930's tile work in the bathroom. The apartment looks down on 59th street, which for the summer months between May and November, hosts the Kegels Beer Garden on the street! We're one of the last Authentic German restaurants and Inn's left in country and the studio apartment is right above it! We hope you love this place as much as we do!

Popular amenities for Greendale vacation rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Milwaukee County
  5. Greendale