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Greendale Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Greendale holiday rentals

A living room with a leather sofa, a round coffee table, and a dining area with a table and chairs.

1. 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, (54 reviews)
"Stayed here many times. Great as always."
United States
Kristi T.
The price is HK$1,390
HK$2,642 total
includes taxes & fees
26 Sept - 27 Sept
Historic home - walk to village center. Original features with modern updates.
A dining area with a ceiling fan, wooden dining table, chairs, and a view of the outdoors through large windows.

2. New Spacious 8-bedroom house on large private lot close to Milwaukee attractions

New Spacious 8-bedroom house on large private lot close to Milwaukee attractions
Milwaukee
10.0 out of 10, Exceptional, (1 review)
"This property was perfect for our needs!"
United States
Amanda D.
The price is HK$1,341
HK$4,188 total
includes taxes & fees
20 Sept - 21 Sept
New Spacious 8-bedroom house on large private lot close to Milwaukee attractions
A bedroom with a bed, bedside table, nightstand, ceiling fan, potted plant, window with blinds, and artwork on the wall.

3. The Plaza Hotel

The Plaza Hotel
3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1,244 reviews)
"Charming stay! Loved the vintage feel... very clean, quiet. A unique place to stay tucked away in a busy city."
United States
Dawn
The price is HK$1,534
HK$1,809 total
includes taxes & fees
12 Oct - 13 Oct
The Plaza Hotel
A modern living room with a sectional sofa, a ceiling fan, large windows, and a TV.

4. Babich Building - 3 Bedroom - Upper Apt #4

Babich Building - 3 Bedroom - Upper Apt #4
West Allis
8.6 out of 10, Excellent, (7 reviews)
"Great property, but a little hot and hard to cool down."
United States
Laura
The price is HK$1,353
HK$3,161 total
includes taxes & fees
14 Sept - 15 Sept
Babich Building - 3 Bedroom - Upper Apt #4
A bar area with a vintage cash register, a wooden counter, and a menu board.

5. Kegel`s Inn - Studio - Classic Apartment #3

Kegel`s Inn - Studio - Classic Apartment #3
West Allis
9.0 out of 10, Wonderful, (6 reviews)
"Great place"
Canada
Zachary
The price is HK$767
HK$1,481 total
includes taxes & fees
14 Sept - 15 Sept
Kegel`s Inn - Studio - Classic Apartment #3
A spacious room with a large table and chairs, large windows with a city view, and a high ceiling with recessed lighting.

6. Deer District Studio Apt - One Block from Fiserv and Baird

Deer District Studio Apt - One Block from Fiserv and Baird
Westown
9.4 out of 10, Exceptional, (29 reviews)
"Great location, clean place, super affordable! Will definitely be booking again!"
United States
Jash
The price is HK$415
HK$1,024 total
includes taxes & fees
14 Sept - 15 Sept
Deer District Studio Apt - One Block from Fiserv and Baird
A modern kitchen with dark cabinets, a white island, blue bar stools, and a window with a view.

7. 6 Mi to Summerfest Park: Home w/ Game Room!

6 Mi to Summerfest Park: Home w/ Game Room!
3.0 star property
Cudahy
The price is HK$1,372
HK$4,092 total
includes taxes & fees
4 Oct - 5 Oct
6 Mi to Summerfest Park: Home w/ Game Room!
Outdoor seating with wicker chairs and red umbrellas, a 'DO NOT ENTER' sign, and a building with 'noodles & company' signage.

8. House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Johnson Woods
9.6 out of 10, Exceptional, (46 reviews)
"Nice quite spot close to highway"
United States
Dan K.
The price is HK$1,247
HK$2,570 total
includes taxes & fees
20 Sept - 21 Sept
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
A living room with a ceiling fan, a sofa, a coffee table, and a dining area with a table and chairs.

9. Charming Bungalow / Heart of Bay View / Parking - Central Air - Deck

Charming Bungalow / Heart of Bay View / Parking - Central Air - Deck
Bay View
10.0 out of 10, Exceptional, (38 reviews)
"Great place to stay in Milwaukee! The house was clean and very well stocked with everything we could need! I didn’t realize someone lived upstairs, but there wasn’t any issues with it. The neighborhood was close to many great things to do We would definitely stay here again!"
United States
Jenna H.
The price is HK$1,412
HK$3,486 total
includes taxes & fees
29 Sept - 30 Sept
Charming Bungalow / Heart of Bay View / Parking - Central Air - Deck
A dining area with a long table, pink chairs, and a chandelier.

10. 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
9.8 out of 10, Exceptional, (27 reviews)
"Great place!"
United States
Kathy R.
The price is HK$1,740
HK$3,152 total
includes taxes & fees
21 Sept - 22 Sept
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers
A dining area with a round table, four chairs, a wooden floor, a door, and a lamp.

11. Quiet House

Quiet House
Milwaukee
8.0 out of 10, Very good, (19 reviews)
"The house was clean, the neighborhood was quiet. The house was very close to the Baird center and other places we wanted to visit."
United States
Steven
The price is HK$529
HK$1,660 total
includes taxes & fees
14 Sept - 15 Sept
Quiet House
A living room with a blue sofa, a yellow armchair, a coffee table, and a large window.

12. Charming 2-bedroom house with everything you need in the heart of West Allis

Charming 2-bedroom house with everything you need in the heart of West Allis
West Allis
9.6 out of 10, Exceptional, (18 reviews)
"Had a great weekend stay. House was clean and cute and our host was very accommodating!"
United States
Renee W.
The price is HK$667
HK$1,724 total
includes taxes & fees
6 Oct - 7 Oct
Charming 2-bedroom house with everything you need in the heart of West Allis
A modern kitchen with grey cabinets, stainless steel appliances, a central island with bar stools, and exposed brick on the wall.

13. Historic Walker’s Point Home, Garage & Yard

Historic Walker’s Point Home, Garage & Yard
Fifth Ward
10.0 out of 10, Exceptional, (10 reviews)
"Great location. Wonderful accommodations. "
United States
Aaron C.
The price is HK$893
HK$2,042 total
includes taxes & fees
14 Sept - 15 Sept
Historic Walker’s Point Home, Garage & Yard
A spacious living room with a spiral staircase, wooden flooring, a large potted plant, and a modern air conditioning unit.

14. Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions

Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions
Lower East Side
9.6 out of 10, Exceptional, (37 reviews)
"Nice location"
United States
Lyndsay K.
The price is HK$1,129
HK$3,458 total
includes taxes & fees
14 Sept - 15 Sept
Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions

15. Best location in Milwaukee! Lower Duplex Unit

Best location in Milwaukee! Lower Duplex Unit
Downtown Milwaukee
9.4 out of 10, Exceptional, (49 reviews)
"Had a great stay at this location. Property manager was very communicative, property was as advertised. Rooms and beds were a good size and comfortable. We didn't do any cooking but the kitchen was well equipped with pots, pans, stove, etc. Located close to the local night life, easily within walking distance. Would happily recommend this property to anyone. "
United States
Chris Y.
The price is HK$820
HK$1,636 total
includes taxes & fees
15 Sept - 16 Sept
Best location in Milwaukee! Lower Duplex Unit
A modern kitchen with light wood cabinets, a stainless steel refrigerator, a stove, and a marble countertop.

16. 3-bedroom bungalow with WiFi vibrant Milwaukee

3-bedroom bungalow with WiFi vibrant Milwaukee
Milwaukee
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful property! We had a great stay!"
United States
VJ P.
The price is HK$1,286
HK$3,560 total
includes taxes & fees
7 Oct - 8 Oct
3-bedroom bungalow with WiFi vibrant Milwaukee

17. Mins to State Fair & AmFam Field |Sleeps 12|4BR + Parking

Mins to State Fair & AmFam Field |Sleeps 12|4BR + Parking
Bluemound Heights
9.4 out of 10, Exceptional, (3 reviews)
"Great place to stay!"
United States
Suzanne S.
The price is HK$1,553
HK$4,677 total
includes taxes & fees
16 Sept - 17 Sept
Mins to State Fair & AmFam Field |Sleeps 12|4BR + Parking
A dining area with a wooden table, a bottle of wine, and glasses. There is a sofa and a bookshelf in the background.

18. Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms

Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms
Bay View
10.0 out of 10, Exceptional, (20 reviews)
"Best stay"
United States
Marvin G.
The price is HK$1,961
HK$4,429 total
includes taxes & fees
30 Sept - 1 Oct
Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms
A modern kitchen with white cabinets, a stainless steel stove, and a wooden countertop.

19. Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!
Downtown Milwaukee
10.0 out of 10, Exceptional, (12 reviews)
"Great stay and great communication throughout. Would stay again, thank you!"
United States
David M.
The price is HK$384
HK$2,099 total
includes taxes & fees
14 Sept - 15 Sept
Remodeled Home - Steps from Brady Street!
A casino interior with neon lighting, slot machines, and a sign for Potawatomi Casino Hotel.

20. Stunning Brewers Hill Retreat with 2 bedrooms & 1 bath

Stunning Brewers Hill Retreat with 2 bedrooms & 1 bath
Brewers Hill
10.0 out of 10, Exceptional, (4 reviews)
"It was a great stay. The home is super clean, in a good location and it has everything you need! "
United States
Michele S.
The price is HK$604
HK$2,043 total
includes taxes & fees
14 Sept - 15 Sept
Stunning Brewers Hill Retreat with 2 bedrooms & 1 bath
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

8/10 Good
"Great experience great food options on property. The staff are friendly and helpful and very informative when checking in."
Raymond 1-night trip
Posted 1 hour 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
  • Use the map to find apartments and other holiday homes in the Greendale neighbourhood you prefer
  • 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 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?

Welcome to the Charming Stone Haven, a beautiful three bedroom property.: This holiday home rental outside of Greendale is located near skiing, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Pettit National Ice Center, or get outside and enjoy nature at Boerner Botanical Gardens. In the wider area, you’ll find Rock Snow Park and American Family Field.

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.