Greendale Vacation Rentals

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Check prices for these dates

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Greendale vacation rentals

Exterior
Historic home - walk to village center. Original features with modern updates.

Historic home - walk to village center. Original features with modern updates.

Historic home - walk to village center. Original features with modern updates.
Greendale
9.8 out of 10, Exceptional, (48)
"Great location and wonderful house. Great location for family with small kids. Parks are super close, downtown street is wonderful to eat and drink. Host is super helpful and responsive. "
United States
Patrick J.
The price is ￥27,684
￥53,274 total
includes taxes & fees
Dec 28 - Dec 29
Historic home - walk to village center. Original features with modern updates.
Premier Room, 1 King Bed | Iron/ironing board, free WiFi, bed sheets
The Plaza Hotel

The Plaza Hotel

The Plaza Hotel
3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1153)
"From check in to check out excellent stay!"
United States
Heather
The price is ￥22,462
￥26,483 total
includes taxes & fees
Jan 25 - Jan 26, 2026
The Plaza Hotel
Lobby
Deer District Studio Apt - One Block from Fiserv and Baird

Deer District Studio Apt - One Block from Fiserv and Baird

Deer District Studio Apt - One Block from Fiserv and Baird
Westown
10.0 out of 10, Exceptional, (2)
"Room was spotless and had great amenities. Great location. "
United States
Philip
The price is ￥7,588
￥18,707 total
includes taxes & fees
Dec 28 - Dec 29
Deer District Studio Apt - One Block from Fiserv and Baird
Fireplace
Kasa Westown Milwaukee

Kasa Westown Milwaukee

Kasa Westown Milwaukee
4.0 star property
Westown
9.0 out of 10, Wonderful, (120)
"Hosts get 5 stars for excellent communication. They checked in with me multiple times on my day of arrival to make sure everything was good and they gave very thorough instructions."
United States
Melissa
Kasa Westown Milwaukee
Smart TV, books, stereo
East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge

East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge

East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge
Downtown Milwaukee
10.0 out of 10, Exceptional, (1)
"We enjoyed our stay at East Side Luxury apartments. Everything was as advertised and it was great staying close to Brady St. We would definitely stay here again."
United States
Greg W.
The price is ￥8,151
￥19,354 total
includes taxes & fees
Dec 28 - Dec 29
East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge
Interior
Downtown Luxury 1BR Loft

Downtown Luxury 1BR Loft

Downtown Luxury 1BR Loft
Downtown Milwaukee
8.8 out of 10, Excellent, (3)
"Recently rehab. Very nice finishes. Safe, quiet, and walkable to many restaurants. "
United States
Brandon
The price is ￥8,455
￥22,434 total
includes taxes & fees
Dec 29 - Dec 30
Downtown Luxury 1BR Loft
Dining
Modern Studio Apt with Skywalk to Fiserv, Rooftop, and Parking

Modern Studio Apt with Skywalk to Fiserv, Rooftop, and Parking

Modern Studio Apt with Skywalk to Fiserv, Rooftop, and Parking
2.0 star property
Westown
10.0 out of 10, Exceptional, (5)
"Great room "
United States
julio
The price is ￥8,151
￥22,049 total
includes taxes & fees
Dec 30 - Dec 31
Modern Studio Apt with Skywalk to Fiserv, Rooftop, and Parking
Fridge, microwave, oven, stovetop
Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!
Downtown Milwaukee
10.0 out of 10, Exceptional, (5)
"Enjoyed stay at this nice home "
United States
Eduardo P.
The price is ￥7,672
￥40,796 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Remodeled Home - Steps from Brady Street!
Game room
Comfort Near Historic Pabst Brewery & Fiserv

Comfort Near Historic Pabst Brewery & Fiserv

Comfort Near Historic Pabst Brewery & Fiserv
2.0 star property
Westown
9.4 out of 10, Exceptional, (14)
"Check-in and parking were easy. Kitchen was well stocked and included some spices. Location was perfect to catch some Brewers games. Beds were comfortable. Will stay again!"
United States
Debra D.
The price is ￥11,523
￥28,976 total
includes taxes & fees
Dec 28 - Dec 29
Comfort Near Historic Pabst Brewery & Fiserv
Paper towels
Stylish Apt in Walker's Point

Stylish Apt in Walker's Point

Stylish Apt in Walker's Point
Fifth Ward
10.0 out of 10, Exceptional, (4)
"I loved my stay here! the location is in a good area near downtown milwaukee with lots of food near by! My stay here was great and the host was very responsive and helpful and provided lots of information. Very cute and aesthetic decor, felt very homey! "
United States
Anthony R.
The price is ￥10,894
￥37,695 total
includes taxes & fees
Dec 28 - Dec 29
Stylish Apt in Walker's Point
Private kitchen
2BR apt w/ laundry + parking

2BR apt w/ laundry + parking

2BR apt w/ laundry + parking
Murray Hill
10.0 out of 10, Exceptional, (12)
"The apartment is clean, spacious and close to the activities we were in town for."
United States
Kelly S.
The price is ￥8,853
￥23,324 total
includes taxes & fees
Jan 5 - Jan 6, 2026
2BR apt w/ laundry + parking
1 bedroom, desk, iron/ironing board
Potter Upper · Bright 1.5BR in the Heart of Bay View - w/ Parking

Potter Upper · Bright 1.5BR in the Heart of Bay View - w/ Parking

Potter Upper · Bright 1.5BR in the Heart of Bay View - w/ Parking
Bay View
10.0 out of 10, Exceptional, (6)
"Nice place "
United States
John B.
The price is ￥6,576
￥25,925 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Potter Upper · Bright 1.5BR in the Heart of Bay View - w/ Parking
Interior
Welcome To My Loft!

Welcome To My Loft!

Welcome To My Loft!
Racine
10.0 out of 10, Exceptional, (16)
"Great place to stay!"
United States
kathleen
The price is ￥10,149
￥17,297 total
includes taxes & fees
Dec 28 - Dec 29
Welcome To My Loft!
Game room
Brewery District Luxe 2BR Near Fiserv with Parking

Brewery District Luxe 2BR Near Fiserv with Parking

Brewery District Luxe 2BR Near Fiserv with Parking
Westown
9.4 out of 10, Exceptional, (6)
"Great location! Super-cool historic building. Easy booking and check-in process, and responsive host. We will be back!"
United States
Christy M.
The price is ￥8,853
￥23,757 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Brewery District Luxe 2BR Near Fiserv with Parking
Interior
Cream City 2BR Apt - Just 3 Blocks to Fiserv with Gym and Parking

Cream City 2BR Apt - Just 3 Blocks to Fiserv with Gym and Parking

Cream City 2BR Apt - Just 3 Blocks to Fiserv with Gym and Parking
Westown
7.8 out of 10, Good, (6)
"It was really nice ,only issue was trying to watch tv, but other than that was good , i would stay there again "
United States
Marty E.
The price is ￥7,307
￥22,876 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cream City 2BR Apt - Just 3 Blocks to Fiserv with Gym and Parking
2 bedrooms
KK lower · Funky 2BR in Prime Bay View - w/ Parking

KK lower · Funky 2BR in Prime Bay View - w/ Parking

KK lower · Funky 2BR in Prime Bay View - w/ Parking
Bay View
10.0 out of 10, Exceptional, (7)
"Charming apartment, convenient location"
United States
Ashton G.
The price is ￥11,242
￥30,906 total
includes taxes & fees
Jan 13 - Jan 14, 2026
KK lower · Funky 2BR in Prime Bay View - w/ Parking
Fridge, microwave, oven, stovetop
Eclectic, Stylish, and Cozy Milwaukee Unit!

Eclectic, Stylish, and Cozy Milwaukee Unit!

Eclectic, Stylish, and Cozy Milwaukee Unit!
2.0 star property
Downtown Milwaukee
9.8 out of 10, Exceptional, (39)
"Great property! We would definitely recommend it and stay again. "
United States
Bridget M.
The price is ￥12,056
￥51,872 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Eclectic, Stylish, and Cozy Milwaukee Unit!
Iron/ironing board, WiFi, bed sheets
Chic MKE Studio | Walk to Beach & Brady St Dining

Chic MKE Studio | Walk to Beach & Brady St Dining

Chic MKE Studio | Walk to Beach & Brady St Dining
2.0 star property
Lower East Side
8.4 out of 10, Very Good, (7)
"Great location and cozy apartment"
United States
Javier O.
The price is ￥9,308
￥25,024 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Chic MKE Studio | Walk to Beach & Brady St Dining
Fridge, microwave, oven, stovetop
Historic Walker’s Point Home, Garage & Yard

Historic Walker’s Point Home, Garage & Yard

Historic Walker’s Point Home, Garage & Yard
2.0 star property
Fifth Ward
10.0 out of 10, Exceptional, (1)
"Five stars all the way!"
United States
Rob K.
The price is ￥23,204
￥45,797 total
includes taxes & fees
Dec 29 - Dec 30
Historic Walker’s Point Home, Garage & Yard
Exterior
Lake Effect Club | The Nohl

Lake Effect Club | The Nohl

Lake Effect Club | The Nohl
2.0 star property
Lower East Side
The price is ￥10,686
￥34,790 total
includes taxes & fees
Dec 28 - Dec 29
Lake Effect Club | The Nohl
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Greendale Hotel Reviews

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

10/10 Excellent
"Rooms a re clean. Roomy, snd very comfortable"
Bob 1-night trip
Posted 1 day ago
Potawatomi Hotel & Casino

Find out more about Greendale

Search for holiday rentals in Greendale on Expedia! You can easily find your home rentals, villas, holiday apartments in Greendale using one of the methods below:

  • View our selection of featured holiday rentals in Greendale
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  • Enter your travel dates to view the best deals on holiday rentals in Greendale while they last

Look no further and take a look at our great range of rental properties in Greendale!

Frequently asked questions

Can I find vacation rentals in Greendale?

Yes, there are vacation rentals close to popular local attractions in Greendale, or you can go with a more remote option if you want a relaxing place to stay. Greendale is known for its restaurants.

What are some of the best vacation rentals that Greendale has to offer?

Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find: This vacation home rental near Greendale is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

How many vacation rentals will I find in Greendale?

Expedia has 5 vacation rentals for your stay in Greendale.

What’s there to see and do in Greendale?

While exploring the area, visit family-friendly sights like Crystal Ridge, or get outside and enjoy nature at Boerner Botanical Gardens. In the larger area, you’ll find Rock Snow Park and The Rock Sports Complex.

What’s a vacation rental in Greendale like?

Vacation rentals are private properties where you can stay for several days or longer in Greendale. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for small groups.