Greendale Vacation Rentals

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Our top choices for Greendale vacation rentals

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, (51 reviews)
"Very clean and nice home.Would definitely recommend "
United States
Glenn T.
$313 nightly
The price is $341
Apr 16 - Apr 17
Total with taxes and fees
Historic home - walk to village center. Original features with modern updates.

Lake Michigan Waterfront Designer Villa

Lake Michigan Waterfront Designer Villa
Racine
9.8 out of 10, Exceptional, (16 reviews)
"The view of Lake Michigan was incredible. Had an amazing "
United States
Lauren O.
$499 nightly
The price is $526
Apr 22 - Apr 23
Total with taxes and fees
Lake Michigan Waterfront Designer Villa

Victorian Hot Tub Oasis steps from Restaurants Pubs Coffee, Grocery & The Beach

Victorian Hot Tub Oasis steps from Restaurants Pubs Coffee, Grocery & The Beach
Shorewood
10.0 out of 10, Exceptional, (4 reviews)
"Great location. 1 block walk to a grocery store, a pharmacy, a great restaurant, AND a great coffee shop. Plenty of space for all."
United States
Nicki U.
$832 nightly
The price is $906
Apr 15 - Apr 16
Total with taxes and fees
Victorian Hot Tub Oasis steps from Restaurants Pubs Coffee, Grocery & The Beach

Serene 4-bedroom house with brook and forest in charming Racine

Serene 4-bedroom house with brook and forest in charming Racine
Racine
$377 nightly
The price is $428
Apr 15 - Apr 16
Total with taxes and fees
Serene 4-bedroom house with brook and forest in charming Racine

Three bedrooms upstairs

Three bedrooms upstairs
Riverwest
9.6 out of 10, Exceptional, (86 reviews)
"Very nice stay in a quaint place. Owner, Ryan, was very nice and hospitable."
United States
Jason D.
$199 nightly
The price is $234
Apr 15 - Apr 16
Total with taxes and fees
Three bedrooms upstairs

Downtown Eastside gem near Fiserv Forum Water St Brady St

Downtown Eastside gem near Fiserv Forum Water St Brady St
Downtown Milwaukee
9.0 out of 10, Wonderful, (48 reviews)
"Walking distance to several great bars, restaurants, breweries and the summer fest area. We really enjoyed our stay!"
United States
SCOTT T.
$280 nightly
The price is $330
Apr 15 - Apr 16
Total with taxes and fees
Downtown Eastside gem near Fiserv Forum Water St Brady St

Charming home w/ fire pit, walk to Lake Michigan

Charming home w/ fire pit, walk to Lake Michigan
Shorewood
9.8 out of 10, Exceptional, (37 reviews)
"Host communication was excellent. House was clean and perfect for a little weekend getaway!"
United States
Grayson P.
$305 nightly
The price is $332
Apr 15 - Apr 16
Total with taxes and fees
Charming home w/ fire pit, walk to Lake Michigan

Near the Airport | Free Breakfast + Pool and Hot Tub

Near the Airport | Free Breakfast + Pool and Hot Tub
Milwaukee
$245 nightly
The price is $280
Apr 20 - Apr 21
Total with taxes and fees
Near the Airport | Free Breakfast + Pool and Hot Tub

Wisconsin Treehouse Getaway!

Wisconsin Treehouse Getaway!
Racine
9.6 out of 10, Exceptional, (29 reviews)
"We had incredible experience/ stay at this place. The host is very friendly and flexible! The place is absolutely gorgeous with amazing view of the lake. Very clean well kept home! Definitely recommend this place!!"
United States
Mohammed A.
$218 nightly
The price is $247
Apr 16 - Apr 17
Total with taxes and fees
Wisconsin Treehouse Getaway!

Rare East Side-2 min walk to UWM-Garage-Lake Mich

Rare East Side-2 min walk to UWM-Garage-Lake Mich
Upper East Side
10.0 out of 10, Exceptional, (2 reviews)
"Loved our stay. Nice clean place that was well stocked."
United States
Patty S.
$252 nightly
The price is $297
Apr 15 - Apr 16
Total with taxes and fees
Rare East Side-2 min walk to UWM-Garage-Lake Mich

Large Milwaukee Home 4BR Fast Wifi

Large Milwaukee Home 4BR Fast Wifi
3.0 star property
Fifth Ward
$679 nightly
The price is $710
Apr 19 - Apr 20
Total with taxes and fees
Large Milwaukee Home 4BR Fast Wifi

Cozy home by the lake

Cozy home by the lake
Cudahy
$571 nightly
The price is $662
Apr 15 - Apr 16
Total with taxes and fees
Cozy home by the lake

Bayview Family-Friendly Stay

Bayview Family-Friendly Stay
Bay View
10.0 out of 10, Exceptional, (2 reviews)
"Best stay ever "
United States
Laniya mariee
$372 nightly
The price is $438
Apr 15 - Apr 16
Total with taxes and fees
Bayview Family-Friendly Stay

Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers
Bay View
9.6 out of 10, Exceptional, (15 reviews)
"Great place!"
United States
Kathy R.
$416 nightly
The price is $491
Apr 21 - Apr 22
Total with taxes and fees
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

3-bedroom vacation home just a short walk to Lake Michigan

3-bedroom vacation home just a short walk to Lake Michigan
Racine
9.2 out of 10, Wonderful, (35 reviews)
"Convenient location, comfortable house, thoughtful amenities, easy walk to lake, quick drive for food and various activities. "
United States
Beth S.
$222 nightly
The price is $252
May 10 - May 11
Total with taxes and fees
3-bedroom vacation home just a short walk to Lake Michigan

The Terrapin Station Hot Tub-Games-Groups of 16+

The Terrapin Station Hot Tub-Games-Groups of 16+
Riverwest
$505 nightly
The price is $596
Apr 21 - Apr 22
Total with taxes and fees
The Terrapin Station Hot Tub-Games-Groups of 16+

Charming 3-bedroom house in lovely Milwaukee near DT and Hospitals

Charming 3-bedroom house in lovely Milwaukee near DT and Hospitals
Morgandale
10.0 out of 10, Exceptional, (3 reviews)
"My kids and I had a great stay here! The location was in a cozy and quiet neighborhood, my kids loved the back yard, and the house itself was very well cared for with comfortable furniture. I’ll definitely be staying there again the next time I’m in town!"
United States
Lauren M.
$525 nightly
The price is $619
Apr 15 - Apr 16
Total with taxes and fees
Charming 3-bedroom house in lovely Milwaukee near DT and Hospitals

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, (9 reviews)
"Charming apartment, convenient location"
United States
Ashton G.
$229 nightly
The price is $234
Apr 16 - Apr 17
Total with taxes and fees
KK lower · Funky 2BR in Prime Bay View - w/ Parking

Relax in Style: 4BR Milwaukee Home ¦ Family-Friendly ¦ Warm & Cozy

Relax in Style: 4BR Milwaukee Home ¦ Family-Friendly ¦ Warm & Cozy
Upper East Side
9.0 out of 10, Wonderful, (6 reviews)
"Our son and his groomsmen stayed here for his wedding weekend. Great accommodations!"
United States
Kathy C.
$357 nightly
The price is $364
Apr 19 - Apr 20
Total with taxes and fees
Relax in Style: 4BR Milwaukee Home ¦ Family-Friendly ¦ Warm & Cozy

Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly

Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly
Murray Hill
10.0 out of 10, Exceptional, (15 reviews)
"We had a wonderful stay and appreciate the hospitality! While in town to visit family and our first trip with an infant, the house had everything we needed making it a comfortable and pleasant first trip! The location was fantastic and allowed for us to easily walk to restaurants, the market and enjoy the sights of the lake! "
United States
Christina T.
$473 nightly
The price is $558
Apr 20 - Apr 21
Total with taxes and fees
Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly
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 $186 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?

7 1/2 Acre Estate, Awesome Farm House with Heated Pool, Hot tub, Fishing Pond: This vacation home rental near Greendale is located on the beach and has an outdoor pool, a fireplace, 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. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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 Milwaukee County Zoo, 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.