Greendale Holiday Rentals

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Holiday Rentals in Greendale

The Plaza Hotel

3.0 star property
8.6 out of 10, Excellent, (1058)
"We appreciated being able to bring our pup to the property for the night. We also appreciated how the parking lot was being maintained/salted during our stay! Thank you"
The price is AU$325
includes taxes & fees
2 Feb - 3 Feb
The Plaza Hotel

Amazing Five Bedroom Milwaukee Vacation Home!!

10.0 out of 10, Exceptional, (40)
"We have a family of 10 and this house was perfect for us. There was entertainment for all ages. Large areas for everyone to gather but also gave everyone their own space. Loved watching movies while swimming in the pool. Host was excellent to work with and process was easy. "
Amazing Five Bedroom Milwaukee Vacation Home!!

Kasa Westown Milwaukee

4.0 star property
9.0 out of 10, Wonderful, (68)
"Excellent location for our family. Will return!"
The price is AU$205
includes taxes & fees
3 Feb - 4 Feb
Kasa Westown Milwaukee

The Malt House

4.0 star property
9.0 out of 10, Wonderful, (2)
"Amazing property/location! Surrounding neighborhood and ambiance is very cool. Not a very upscale property/bedding/furniture. However, a fine tradeoff for price and ambience. The parking access during winter is also a nice touch"
The price is AU$261
includes taxes & fees
3 Feb - 4 Feb
The Malt House

Seven Acre Estate, Fishing Pond, Events! Winter Discounts! Weddings, Heated pool

9.8 out of 10, Exceptional, (196)
"Great property"
The price is AU$977
includes taxes & fees
1 Mar - 2 Mar
Seven Acre Estate, Fishing Pond, Events! Winter Discounts! Weddings, Heated pool

Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

9.8 out of 10, Exceptional, (328)
"Grant has an excellent property and was fantastic in communication! He went above and beyond for sure! "
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

Prospect

3.0 star property
8.0 out of 10, Very good, (3)
"The lodging was just what I needed for my short stay. The only problem I experienced (which is a very important to me) was the in ability to control the heating. Its either on or off. When its off, it's going to get super cold and when its on, it will get super hot and uncomfortable. I had to open the window often to cool of. "
The price is AU$216
includes taxes & fees
3 Feb - 4 Feb
Prospect

Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

9.8 out of 10, Exceptional, (18)
"Charming historical area with plenty of street parking. This unit was spacious, smartly renovated and clean. We would stay here again and recommend to others.again. "
The price is AU$925
includes taxes & fees
2 Feb - 3 Feb
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

Sleeps up to 30 people comfortably, there's karaoke pool table and so much more.

8.0 out of 10, Very good, (9)
"We were unable to check in until several hours after the check in time due to a plumbing issue the host did not proactively communicate about. Host did not use the entry keypad code they requested we set. The listing indicated 7 bedrooms for a total of 2 king beds, 1 queen, 10+ twin beds, and additional futons. On arrival there was only 1 double bed, 10 twin beds, a couple of futons. We had to make alternate accommodations for half our group. The host did not respond to outreach at all the first...
The price is AU$1,352
includes taxes & fees
2 Feb - 3 Feb
Sleeps up to 30 people comfortably, there's karaoke pool table and so much more.

MKE Mansion - Both Wings

9.8 out of 10, Exceptional, (12)
"The house is exactly as listed. There were some small functional issues with the house that the landlord responded to immediately. All around great stay. "
The price is AU$2,402
includes taxes & fees
2 Feb - 3 Feb
MKE Mansion - Both Wings

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

9.8 out of 10, Exceptional, (19)
"This home was so welcoming and easy to stay at! Without fuss, I cooked up groceries we bought and walked the dog to a near by park. After dinner we took a short drive to play darts and were welcomed by the neighborhood bar as if we were locals. When my husband snored too loud, the additional guest rooms were just as comfortable as the master. The sweet sitcom decor reminds you to appreciate the history you can still feel in the home; the backyard was wonderful and secure; the kitchen made sense...
The price is AU$425
includes taxes & fees
16 Feb - 17 Feb
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

Spacious Pewaukee Lake/ Pier Access Home

8.6 out of 10, Excellent, (11)
"Our company needed to send workers out of town to a job site in the Delafield area. The house was perfect for our needs, close to the job site and enough beds for each person. That is always our struggle, enough beds, they will share a room but not a bed. Our employees enjoyed being able to sit out after a long day and sit around the fire pit and relax. Steve was great to work with, as we needed to book an additional week and despite having availability VRBO site showed it unavailable. We...
Spacious Pewaukee Lake/ Pier Access Home

225- Huge 2 bedroom condo king beds-Free parking-extras

9.0 out of 10, Wonderful, (17)
"Overall a nice place to stay but getting to the building from the parking ramp was difficult. Needs one more chair in the living room for adequate seating, a few more bathroom towels, knife block with knives and scissors. Back bedroom window has a terrible draft it was extremely cold in that bedroom. "
225- Huge 2 bedroom condo king beds-Free parking-extras

15 minutes to anywhere in and around Milwaukee.

10.0 out of 10, Exceptional, (30)
"Was not expecting to be in the basement of a home that they created into a little apartment. The home owner showed us to the lockbox and explained everything on getting in and out. There were house rules like quiet hours after 10pm which would have been good to know, it was NYE and we wanted to play music after our concert but we were to scared to be loud or wake up the home owner. There was also only one bathroom connected to the bedroom so any friends sleeping on the couch in the living room...
The price is AU$269
includes taxes & fees
2 Feb - 3 Feb
15 minutes to anywhere in and around Milwaukee.

Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10

9.6 out of 10, Exceptional, (233)
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Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10

Lake Michigan Waterfront Designer Villa

9.8 out of 10, Exceptional, (6)
"this vrbo is by far one of the best i have stayed at. it's so nice to be in a home that feels like it is loved by its owners. we were celebrating my partner's 30th birthday and had a group of 10 stay very comfortably (we could easily have had more!) the location is easy to find but still feels secluded even though there are neighbors close by. i can't imagine how amazing this place is in the summer when you can use the pool and swim in the lake! still, we saw a bald eagle so i can't complain :)...
The price is AU$927
includes taxes & fees
18 Feb - 19 Feb
Lake Michigan Waterfront Designer Villa

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

9.8 out of 10, Exceptional, (12)
"Great stay by the snow covered beach great communication"
The price is AU$349
includes taxes & fees
14 Feb - 15 Feb
3-bedroom vacation home just a short walk to Lake Michigan

Step right up, step right up! Welcome to the grand, the unique, the unparalleled

9.8 out of 10, Exceptional, (67)
"The house was very roomy and lots of places to hang out with family and friends. It was awesome that it was close to the lake. The owner had forgotten we were coming and didn’t have the refrigerator cleaned out and our check-in process was a little awkward because we didn’t have the keypad information. "
Step right up, step right up! Welcome to the grand, the unique, the unparalleled

Barn! B-Ball Court/Mini Golf/Sports Bar/Tiki Bar/Theater/Arcade/Hot Tub/Fire Pit

10.0 out of 10, Exceptional, (7)
"This fulfilled house was perfect for extended family to gather for the holiday! Everyone had something to do and plenty room to gather together for meals and activities. "
Barn! B-Ball Court/Mini Golf/Sports Bar/Tiki Bar/Theater/Arcade/Hot Tub/Fire Pit

Wisconsin Treehouse Getaway!

9.8 out of 10, Exceptional, (19)
"Thank you for allowing us to stay in another of your incredible properties ... Enjoyed a nice getaway with my wife. Beautiful location with a creek running along the back of the property. Look forward to seeing you soon .. Thank you, Will & Brenda"
The price is AU$426
includes taxes & fees
4 Feb - 5 Feb
Wisconsin Treehouse Getaway!
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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Other types of properties in Greendale you may be interested in

Saint Kate - The Arts Hotel

4.0 star property
9.8 out of 10, Exceptional, (2171)
"This is one of the coolest, most interesting hotels we've ever stayed at, and we travel a fair amount. I took one star off for service because the wait staff at Aria forgot the chopsticks with the sushi (which was surprisingly good) and were a bit slow to clear dishes. Otherwise, exceptional in every way. "
The price is AU$245
includes taxes & fees
23 Feb - 24 Feb
Saint Kate - The Arts Hotel

Hilton Milwaukee

4.0 star property
8.2 out of 10, Very good, (1062)
"Beautiful architecture "
The price is AU$195
includes taxes & fees
23 Feb - 24 Feb
Hilton Milwaukee

The Pfister Hotel

4.5 star property
9.4 out of 10, Exceptional, (1615)
"Staff were friendly and accommodating. Great location. The pool on the 23rd floor had great views."
The price is AU$280
includes taxes & fees
2 Mar - 3 Mar
The Pfister Hotel
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.

Frequently asked questions

Can I find holiday rentals in Greendale?

Yes, there are holiday rentals close to the most popular sights in Greendale, or you can select a more secluded option if you're looking for a relaxing stay. Greendale is known for its restaurants.

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

Amazing Five Bedroom Milwaukee Vacation Home!!: This holiday home rental outside of Greendale offers an indoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a balcony and a garden.

How many holiday rentals will I find in Greendale?

Expedia has 5 holiday 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 wider area, you’ll find Rock Snow Park and The Rock Sports Complex.

What’s a holiday rental in Greendale like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Greendale. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a family trip or a small group gathering.