Places to stay in Greendale

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Top-rated places to stay in Greendale

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Top guest favorite

A living room is presented with a gray sofa, a minimalist table, and wooden chairs. Natural light enters through large windows, accentuated by decorative curtains. A patterned area rug covers the floor, while a ceiling fan hangs above, contributing to the room's comfortable ambiance.

Apartment in West Allis

4.97 out of 5 average rating, 162 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!

Top guest favorite

A verdant backyard is surrounded by mature trees, providing shade to the manicured lawn. A stone path meanders through the garden, leading past a small seating area with white chairs. Lush greenery and flower beds enhance the inviting outdoor space.

Bungalow in Wauwatosa

4.97 out of 5 average rating, 226 reviews

Wauwatosa/Milwaukee “Inglewood Place”Classic 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.

Guest favorite

Apartment in Bay View

4.95 out of 5 average rating, 325 reviews

Bay View MKE Hideaway - with Parking!

Cozy, inviting, one bedroom apartment in the heart of Bayview, literally steps away from some of Milwaukee's best restaurants, bars and shops! One of two Airbnb guest spaces in our house, this downstairs apartment is our home base when we're in Milwaukee, and we love sharing it with guests when we’re on the road! We are within five minutes of Summerfest grounds and East Side & Historic Third Ward districts, and within 10 minutes of the airport, downtown, Marquette University, and Miller Park.

Top guest favorite

An oval wooden frame surrounds a vintage portrait of a man dressed in formal attire, depicting a rich historical context. The muted colors offer a classic touch to the decor, enhancing the atmosphere of the home while inviting curiosity about its past.

Home in Greendale

5 out of 5 average rating, 55 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

4.83 out of 5 average rating, 70 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

Bungalow in West Milwaukee

4.97 out of 5 average rating, 176 reviews

Adorn Abode

Charming upper level hygge bungalow (2 unit home total). Ten minutes from anywhere. Tucked away in the quiet village of West Milwaukee. Full of natural light and curated vintage decor. Walking distance to a few restaurants and bars, as well as the American Family Field. Enjoy a cocktail on the front balcony and watch the sunset while indulging in a classic vinyl collection. Small balcony off of the kitchen to watch the sunrise and enjoy a cup of coffee. Perfect for adventuring or relaxing.

Guest favorite

A tiled shower space features natural stone walls in varying shades of gray. A built-in bench is positioned against the wall, and a white towel hangs from a metal towel bar. A bottle of shampoo is placed on the floor near the shower drain.

Apartment in Wauwatosa

4.85 out of 5 average rating, 324 reviews

Tosa Village Studio Apartment

Tosa Village Studio. (Wauwatosa is the first suburb west of Milwaukee). Walk to the Village and explore the boutique shops, restaurants and bars. Enjoy summer concerts in Hart Park. Miller Park (Milwaukee County Stadium - Home of the Brewers) only 3.5 miles away. Close to the Medical Complex, Froedert and Children's Hospitals. 6.5 miles to the Fiserv Forum (Home of the Milwaukee Bucks). Six miles to downtown Milwaukee. Enjoy Summerfest at the Lake Michigan shore.

Superhost

A panoramic view of a baseball stadium is captured from above, displaying a well-maintained green field surrounded by seating areas. The roof is partially open, allowing natural light to flood the venue. Blue skies and white clouds enhance the vibrant atmosphere of the stadium.

Apartment in West Allis

4.8 out of 5 average rating, 303 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!

Guest favorite

A well-stocked cheese display case is seen in a warmly lit store. Various cheeses are organized neatly with clear labels, showcasing a wide variety of colors and textures. Shelves in the background contain additional specialty foods and beverages, contributing to the inviting shopping atmosphere.

Apartment in West Allis

4.91 out of 5 average rating, 329 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.

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, 202 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.

Top guest favorite

A well-lit outdoor deck features a hot tub with soft blue lighting, surrounded by wooden fencing. Two wicker chairs are positioned on the side, with planters and a bench integrated into the space. Twinkling string lights enhance the evening ambiance.

Home in Wauwatosa

5 out of 5 average rating, 253 reviews

The Little Gray House

It's summer! The garden is in full bloom! Stay with us and enjoy all the amenities of the Little Gray House including a shed bar with food truck style windows and TV, hot tub, comfortable bedrooms and more! We've also just added a tankless water heater - never run out of hot water! The Little Gray House has attained rave reviews from travelers around the world for its comfort, cleanliness, and convenience. Happy to have you!

Guest favorite

Home in West Allis

4.95 out of 5 average rating, 237 reviews

Near to all Milwaukee favorites/ Free Parking/WiFi

Make yourself, family or friends at home in this Cozy comfortable upper 2 bedroom, 1 bathroom house with Wisconsin charm! It’s a great location in the city of West Allis just a short drive to everywhere in Milwaukee. I appreciate that you considered my Airbnb listing! Please feel free to contact me on how I can improve your stay. Also, please take a moment to review my house rules. Can wait to host you, thanks!!!

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Popular amenities for Greendale places to stay

Self check-in

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Guest favorite

An open area is featured, displaying hardwood flooring and neutral-toned walls. A round table with four chairs sits in the foreground, while a workspace with a chair is positioned nearby. Shelves with woven baskets are mounted on the wall, and a window provides natural light.

Apartment in Wauwatosa

4.95 out of 5 average rating, 40 reviews

Cozy Renovated Retreat in Tosa

AndreyaRating, 5 stars1 day ago

This place was perfect for two. Cozy and cute, safe neighborhood. Great and friendly communication from the host.

Guest favorite

Home in Hales Corners

4.81 out of 5 average rating, 32 reviews

Green space to stay

RitikaRating, 5 stars1 month ago

This Airbnb was by far one of the best that I’ve stayed at! It was within a 20 minute drive to everywhere my boyfriend and I wanted to go and it was a gorgeous place, I felt right at home! I would definitely stay here again when I come to Milwaukee in the future! Thank you Chema for allowing my boyfriend and I in your beautiful home

Place to stay in Racine

4.86 out of 5 average rating, 719 reviews

Wisconsin Treehouse Getaway!

ArielRating, 5 stars6 days ago

Beautiful space and property. Had a great stay and made wonderful memories. Main thing I’d say to be aware of is it is connected to the hosts’ actual home so keep that in mind. While the space is private, it’s not isolated. You may interact or hear the hosts’ family along the way. It wasn’t a big deal for us, but something to think about if you’re not fond of or used to it. Overall, great stay and recommend!

Top guest favorite

A serene garden area features twinkling string lights hung above a small round table and a chair, set on lush green grass. A wooden lattice fence provides privacy, while dense greenery surrounds the space, enhancing the peaceful atmosphere.

Guest suite in Wauwatosa

4.9 out of 5 average rating, 63 reviews

Private Tosa Guest Suite, Hidden Gem in Paradise

JQRating, 5 stars5 days ago

It’s a nice and clean room in a quiet neighborhood. The room was bigger than I thought and had everything I needed. Amanda was friendly and helpful. Totally recommended!

A charming white house is framed by vibrant autumn foliage. A paved path leads to the entrance, flanked by two large decorative planters. The fully fenced yard features well-maintained grass and tasteful landscaping, creating an inviting first impression.

Home in Greendale

4.78 out of 5 average rating, 76 reviews

Entire Home, Mainstreet Historic Greendale

RhondaRating, 5 stars1 week ago

We found the unit clean and consistent with all that was described. We thoroughly enjoyed our stay !

Two hanging chairs positioned on a wooden deck offer a comfortable seating area overlooking a lush green landscape. A fire pit table stands in the center, providing a focal point for gatherings. Clear blue skies enhance the inviting outdoor space.

Guesthouse in Franklin

4.83 out of 5 average rating, 6 reviews

The Crows Nest Cottage 1

DeepaRating, 5 stars1 day ago

We booked this last minute since we needed a place for a week or so. This seemed to be the best around that matched our dates. I had to choose between the small cabin for the 3 of us and a bigger place in Milwaukee without much green space or guaranteed parking or even unsure about safety. I am glad we chose this one. Adam has designed the place very tastefully. The big scenic backyard makes it completely worth staying just for that. I loved watching the sunrise from the treehouse in the morning and sitting outside to get my work done. It gave us enough space to spread out and do our things. The kitchen was well stocked with utensils and coffee pods. There were enough linens and sheets. It was very easy to move the coffee table to use the daybed. I wish we had the time to check out his boat rental. Adam is very responsive and friendly. He was very accommodating since reached very late. We enjoyed having his presence and his house nearby even though we are not usually social.

Top guest favorite

Home in Saint Francis

5 out of 5 average rating, 12 reviews

South Shore Guesthouse

CraigRating, 5 stars5 days ago

Where do I begin...Everything was absolutely perfect! Kristyna has her home set up like a 5-star hotel! She provided anything & everything a person could need or want. She made us feel very welcomed, from the beautiful set up of the home to the extras that she provided, including fresh flowers on the extra large island in the kitchen. We loved everything about this home! Thank you Krystyna!

Guest favorite

The spacious community outdoor deck features modern seating options, including a white sofa and a wooden dining table with chairs. Floor-to-ceiling glass walls provide views of the surrounding buildings, while the layout is designed for relaxation and social gatherings.

Apartment in Lower East Side

4.94 out of 5 average rating, 36 reviews

Luxury Studio Apt UR4 Near Brady+Balcony+Lake View

BrandtRating, 5 stars2 weeks ago

Great place in great location!! Host was very prompt in any questions we had! Very clean and great view of Lake Michigan! Would definitely stay there again!!

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Places to stay in Greendale

Top-rated places to stay in Greendale

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