Greendale Vacation Rentals

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Our top choices for Greendale vacation rentals

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.
$313 nightly
The price is $341
Dec 30 - Dec 31
Total with taxes and fees
Historic home - walk to village center. Original features with modern updates.

Aparthotel in Downtown Milwaukee

The Plaza Hotel
3.0 star property
8.8 out of 10, Excellent, (1153)
"From check in to check out excellent stay!"
United States
Heather
$147 nightly
The price is $174
Jan 18 - Jan 19, 2026
Total with taxes and fees
The Plaza Hotel
10.0 out of 10, Exceptional, (2)
"Room was spotless and had great amenities. Great location. "
United States
Philip
$104 nightly
The price is $120
Jan 4 - Jan 5, 2026
Total with taxes and fees
Deer District Studio Apt - One Block from Fiserv and Baird

Aparthotel in Westown

Kasa Westown Milwaukee
4.0 star property
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
$155 nightly
The price is $183
Jan 6 - Jan 7, 2026
Total with taxes and fees
Kasa Westown 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.
$107 nightly
The price is $124
Jan 4 - Jan 5, 2026
Total with taxes and fees
East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge

Apartment in Downtown Milwaukee

Downtown Luxury 1BR Loft
8.8 out of 10, Excellent, (3)
"Recently rehab. Very nice finishes. Safe, quiet, and walkable to many restaurants. "
United States
Brandon
$124 nightly
The price is $143
Dec 29 - Dec 30
Total with taxes and fees
Downtown Luxury 1BR Loft
10.0 out of 10, Exceptional, (5)
"Great room "
United States
julio
$122 nightly
The price is $141
Dec 30 - Dec 31
Total with taxes and fees
Modern Studio Apt with Skywalk to Fiserv, Rooftop, and Parking

Vacation Home in Downtown Milwaukee

Remodeled Home - Steps from Brady Street!
10.0 out of 10, Exceptional, (5)
"Enjoyed stay at this nice home "
United States
Eduardo P.
$225 nightly
The price is $265
Dec 29 - Dec 30
Total with taxes and fees
Remodeled Home - Steps from Brady Street!
2.0 star property
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.
$198 nightly
The price is $212
Jan 3 - Jan 4, 2026
Total with taxes and fees
Comfort Near Historic Pabst Brewery & Fiserv

Apartment in Fifth Ward

Stylish Apt in Walker's Point
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.
$209 nightly
The price is $246
Dec 29 - Dec 30
Total with taxes and fees
Stylish Apt in Walker's Point

Apartment in Murray Hill

2BR apt w/ laundry + parking
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.
$128 nightly
The price is $150
Jan 5 - Jan 6, 2026
Total with taxes and fees
2BR apt w/ laundry + parking
10.0 out of 10, Exceptional, (6)
"Nice place "
United States
John B.
$162 nightly
The price is $166
Jan 14 - Jan 15, 2026
Total with taxes and fees
Potter Upper · Bright 1.5BR in the Heart of Bay View - w/ Parking

Apartment in Racine

Welcome To My Loft!
10.0 out of 10, Exceptional, (16)
"Great place to stay!"
United States
kathleen
$105 nightly
The price is $111
Dec 31 - Jan 1, 2026
Total with taxes and fees
Welcome To My Loft!
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.
$132 nightly
The price is $152
Jan 1 - Jan 2, 2026
Total with taxes and fees
Brewery District Luxe 2BR Near Fiserv with Parking
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.
$127 nightly
The price is $147
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cream City 2BR Apt - Just 3 Blocks to Fiserv with Gym and Parking
10.0 out of 10, Exceptional, (7)
"Charming apartment, convenient location"
United States
Ashton G.
$194 nightly
The price is $198
Jan 13 - Jan 14, 2026
Total with taxes and fees
KK lower · Funky 2BR in Prime Bay View - w/ Parking

Apartment in Downtown Milwaukee

Eclectic, Stylish, and Cozy Milwaukee Unit!
2.0 star property
9.8 out of 10, Exceptional, (39)
"Great property! We would definitely recommend it and stay again. "
United States
Bridget M.
$291 nightly
The price is $343
Jan 11 - Jan 12, 2026
Total with taxes and fees
Eclectic, Stylish, and Cozy Milwaukee Unit!
2.0 star property
8.4 out of 10, Very Good, (7)
"Great location and cozy apartment"
United States
Javier O.
$143 nightly
The price is $152
Jan 3 - Jan 4, 2026
Total with taxes and fees
Chic MKE Studio | Walk to Beach & Brady St Dining
2.0 star property
10.0 out of 10, Exceptional, (1)
"Five stars all the way!"
United States
Rob K.
$257 nightly
The price is $293
Dec 29 - Dec 30
Total with taxes and fees
Historic Walker’s Point Home, Garage & Yard

Vacation Home in Lower East Side

Lake Effect Club | The Nohl
2.0 star property
$188 nightly
The price is $222
Dec 29 - Dec 30
Total with taxes and fees
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

Find out more about Greendale

Everything you need to know about Greendale vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greendale vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greendale vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greendale vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greendale. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Greendale in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $174 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Greendale rentals

At Expedia, we put the best Greendale vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Greendale rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greendale vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greendale. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.