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 favorite

A spacious living area features a cozy tufted sofa adorned with decorative pillows, complemented by a circular glass coffee table. A vibrant area rug with floral patterns enhances the warm wood floors. Colorful artwork decorates the walls, adding a playful touch to the room.

Home in Bay View

4.91 out of 5 average rating, 105 reviews

2BR Sunny Upper in Prime Bay View - w/ Parking

Perfectly located on the main strip of KK in Milwaukee’s eclectic Bay View directly next to bars, restaurants, and shopping. Minutes from downtown, Summerfest, art museum. You’ll have the entire 2nd floor of this sunny duplex. Stylishly designed - 2 bedrooms with Casper mattresses, a bright kitchen with seating area, a work space in the master, and a comfy living room with a smart TV. The space has 2 patio spaces, a small backyard area, an in-unit washer & dryer as well as 1 free parking space.

Guest favorite

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

4.93 out of 5 average rating, 27 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!

Top guest favorite

The exterior of a two-story brick duplex is shown, featuring a welcoming entrance. Lush green lawns are bordered by manicured flower beds. Steps lead to the front door, flanked by hanging flower baskets and illuminated by wall-mounted lanterns. A concrete pathway curves gently through the yard.

Bungalow in Wauwatosa

4.97 out of 5 average rating, 233 reviews

Wauwatosa/MKE “Inglewood Place” Historic Charm

Great location near all Milwaukee attractions and village of Wauwatosa.Cozy upper two-bedroom duplex with keyless entry in quiet east Tosa. Extras such as ironed sheets, snacks and personal items are included. Walk to popular restaurants and bars 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. Near AmFam Field (Brewers stadium) and the lakefront. 4 miles to downtown Milwaukee.

Top guest favorite

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, 60 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.

Superhost

A modern kitchen features sleek cabinetry and a wood-paneled ceiling. Countertops are equipped with essential cooking tools and a deep sink. Natural light filters through window coverings, illuminating a small dining set at the far end, enhancing the kitchen's inviting functionality.

Home in Greendale

4.78 out of 5 average rating, 74 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!

Top guest favorite

The exterior of the vintage 1938 home features a white façade with multiple windows and a welcoming porch adorned with decorative railings. Natural light creates playful shadows on the walls, highlighting the architectural details and lush greenery surrounding the property.

Townhouse in Greendale

4.91 out of 5 average rating, 92 reviews

Entire home, ideal for families & pets.

Entire cozy, historic 1938 home. No extra cleaning or guest service fee! Family & Pet Friendly. Steps from playground or historic Village Center w/shopping, fine dining, wine bar; 15 min to downtown MKE or Airport; 6 min from Rock Sports Complex or WI State Fair Park. Full kitchen; Laundry, Central AC, Hi Speed Wi-Fi; ample work space. Free off street parking. Plush towels and toiletries in bathrooms. Enjoy your visit to this historic garden community. Sleeps 7. Over 70 “5 Star” Reviews.

Guest favorite

The historic home, designed in a Queen Anne Victorian style, features a white exterior with intricate woodwork. Large windows reflect soft evening light, while a spacious porch offers a welcoming entry. The surrounding yard is open, with mature trees that provide shade and a natural ambiance.

Home in Wales

4.95 out of 5 average rating, 128 reviews

Charming, Updated and Historic

This is truly a memorable, charming, and welcoming place to stay. You will have the home to yourself. You will love the warm feel, woodwork, and historical prominence of this home. It is very charming throughout and is on a large 1.5-acre estate size lot. The price quoted here is for 1-2 people and a 1 Bedroom suite with 1.5 Baths. Under this listing we can open up to three suites and accept six guests. If need more there than 2 guests and 1 suite we are happy to make you a custom offer.

Top guest favorite

A welcoming living area features a spacious gray sectional sofa arranged around a coffee table. A textured area rug adds warmth, while large windows provide natural light. Green plants and wall accents enhance the cozy ambiance, and the open layout leads towards the kitchen.

Home in Franklin

5 out of 5 average rating, 40 reviews

The Rawson House

Fully renovated 3 bedroom and 2 bath home. Walking distance to the Rock sports complex. Perfect for groups looking to discover all the great activities that Franklin and Milwaukee have to offer. Walking distance to Franklin Field, the home of the Milwaukee Milkmen. Enjoy a drink at the Umbrella Bar, hit some golf balls at the brand new Luxe Golf Bays, or enjoy local restaurants. Perfect for groups attending weddings or other events at The Lodge. Also, a quick drive to downtown Milwaukee.

Superhost

A paved walkway leads to a historic dwelling surrounded by lush greenery. A covered entrance is visible, framed by trees and colorful flower beds. The serene front yard features well-maintained grass, inviting a peaceful ambiance.

Townhouse in Greendale

4.79 out of 5 average rating, 66 reviews

Historic Greendale, Milwaukee Attractions

A Greendale "original" designated historic dwelling within walking distance of the quaint village of downtown Greendale. Walk to Ricardo's pizza, Vintage 38, Joey Gerard's, The Eleanor Room and Panther Pub. Also, local boutique shops. Greendale also hosts some local festivals year-round, outdoor concerts at the Gazebo and Farmer's market. A short drive from Milwaukee and all this great city has to offer. New 55 inch smart TV in family room! New comfort height toilet!

Top guest favorite

A spacious bedroom features a white bed adorned with decorative pillows and a textured throw blanket. A striking lion portrait hangs above the bed. Natural light fills the room through a nearby window, with soft curtains partially drawn, complementing the warm brown walls.

Home in Milwaukee

4.94 out of 5 average rating, 209 reviews

Mid-Century Inspired Upper Duplex in Bay View

Step through the carpeted private entrance of this 2nd floor home, and into a mid-century interior with a modern twist. Eye-catching touches include the collection of retro radios that give it its name, stylish decor and a subway-tiled bathroom. This cozy apartment is decorated in a mid-century theme with a modern twist. It's on the second floor of a duplex. You will have your own carpeted entrance located in the back of the property.

Guest favorite

The bright living area features tall, arched windows allowing natural light to fill the space. A spacious sectional sofa is adorned with various textured throw pillows, while a colorful area rug anchors a wooden coffee table. Decorative plants and wall art enhance the airy atmosphere.

Apartment in Walker's Point

4.98 out of 5 average rating, 183 reviews

Cozy Vibes Apt | City View | Gym | Free Parking

Cream City historical brick building with incredible views of signature landmarks of Walkers Point. Cozily designed space by interior designer to make a romantic getaway or personal solo retreat to concentrate on your higher purpose. Very safe building and walking distance from foodie restaurants, breweries, jazz clubs, and the famed Iron Horse hotel. A perfect getaway for you and yours.

Top guest favorite

A geodesic dome is positioned within a natural setting, featuring a glossy, multicolored exterior. A landscaped area surrounds the dome, with stones outlining the flower beds filled with vibrant plants. Lush greenery and trees create a serene backdrop for this unique structure.

Dome in Caledonia

5 out of 5 average rating, 56 reviews

Indigo Zen Garden

Our glamping site features a cozy Dome with an open roof for stargazing, a fully furnished bedroom tent, and a second tent designed just for kids—filled with toys, a mud kitchen, and sandpit. Unwind under the gazebo with a fire table, gather by the fire pit , under the stars. Add some magic with twinkling lights, starry skies, and an optional outdoor movie night with popcorn under the stars.