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Greendale Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Greendale vacation 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, (56 reviews)
"Stayed here many times. Great as always."
United States
Kristi T.
The price is CA $253
CA $493 total
includes taxes & fees
Oct 13 - Oct 14
Historic home - walk to village center. Original features with modern updates.
A bar area with a vintage cash register, a wooden counter, and a menu board.

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

Kegel`s Inn - Studio - Classic Apartment #3
West Allis
9.0 out of 10, Wonderful, (7 reviews)
"Great place"
Canada
Zachary
The price is CA $139
CA $269 total
includes taxes & fees
Oct 13 - Oct 14
Kegel`s Inn - Studio - Classic Apartment #3
A bedroom with a bed, bedside table, lamp, and a painting of a beach scene.

3. Fast WiFi - Underground Parking - King Bed - Near Froedtert

Fast WiFi - Underground Parking - King Bed - Near Froedtert
Wauwatosa
9.8 out of 10, Exceptional, (26 reviews)
"Everything was great! I definitely book again!"
United States
Lucas Y.
The price is CA $99
CA $343 total
includes taxes & fees
Oct 12 - Oct 13
Fast WiFi - Underground Parking - King Bed - Near Froedtert
A bedroom with a bed, bedside chairs, a desk, a TV, and a window with a view.

4. Westown Studio Apt Near Fiserv, Baird, and Theater District · Sleeps 4

Westown Studio Apt Near Fiserv, Baird, and Theater District · Sleeps 4
Westown
9.6 out of 10, Exceptional, (4 reviews)
"Great location. Lovely place."
United States
Jennifer
The price is CA $294
CA $449 total
includes taxes & fees
Oct 24 - Oct 25
Westown Studio Apt Near Fiserv, Baird, and Theater District · Sleeps 4
A bedroom with a bed, bedside table, nightstand, ceiling fan, potted plant, window with blinds, and artwork on the wall.

5. The Plaza Hotel

The Plaza Hotel
3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1,256 reviews)
"Parking was reasonable and close by"
United States
Danita
The price is CA $205
CA $242 total
includes taxes & fees
Nov 2 - Nov 3
The Plaza Hotel
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

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

Deer District Studio Apt - One Block from Fiserv and Baird
Westown
9.0 out of 10, Wonderful, (7 reviews)
"Host was friendly and responded promptly and was very accommodating! "
United States
Drew W.
The price is CA $82
CA $218 total
includes taxes & fees
Oct 12 - Oct 13
Deer District Studio Apt - One Block from Fiserv and Baird
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove. There are three black bar stools and pendant lights above the island.

7. Luxury Downtown Apt with Parking, Gym, and Lap Pool · Sleeps 4-5

Luxury Downtown Apt with Parking, Gym, and Lap Pool · Sleeps 4-5
Downtown Milwaukee
9.0 out of 10, Wonderful, (7 reviews)
"Great space, I enjoyed it very much. Location was perfect, building and parking were great, and the apartment was very comfortable and clean "
United States
Kara B.
The price is CA $107
CA $255 total
includes taxes & fees
Oct 18 - Oct 19
Luxury Downtown Apt with Parking, Gym, and Lap Pool · Sleeps 4-5
A modern kitchen with a large island, dark cabinetry, stainless steel appliances, and a city view through large windows.

8. Modern Luxury 1BR Apt with Rooftop, Gym, and Parking

Modern Luxury 1BR Apt with Rooftop, Gym, and Parking
Westown
9.4 out of 10, Exceptional, (31 reviews)
"Beautiful view, bright and clean, great location "
Canada
Breanna
The price is CA $85
CA $214 total
includes taxes & fees
Nov 2 - Nov 3
Modern Luxury 1BR Apt with Rooftop, Gym, and Parking
A living room with a sofa, a coffee table, a fireplace, a TV, and a bar area with a chair.

9. Cozy Modern Apartment w/ Parking – Close to Downtown

Cozy Modern Apartment w/ Parking – Close to Downtown
Marquette
8.8 out of 10, Excellent, (3 reviews)
"Very cozy, gave me homie vibes."
United States
Mireya
The price is CA $140
CA $241 total
includes taxes & fees
Oct 14 - Oct 15
Cozy Modern Apartment w/ Parking – Close to Downtown
A modern kitchen with a large island, built-in appliances, and ample natural light.

10. East Side Luxury 1BR Apt · Near Brady St with Balcony and Lounge · Sleeps 4

East Side Luxury 1BR Apt · Near Brady St with Balcony and Lounge · Sleeps 4
Downtown Milwaukee
10.0 out of 10, Exceptional, (2 reviews)
"Was super convenient and clean!"
United States
Jessa H.
The price is CA $83
CA $187 total
includes taxes & fees
Oct 12 - Oct 13
East Side Luxury 1BR Apt · Near Brady St with Balcony and Lounge · Sleeps 4
A modern kitchen with a central island, bar stools, and pendant lighting.

11. Downtown Luxe 2BR Loft Apt | Sleeps 8 | Walkable

Downtown Luxe 2BR Loft Apt | Sleeps 8 | Walkable
Downtown Milwaukee
10.0 out of 10, Exceptional, (6 reviews)
"Easy entry and check out. The unit has great light and open with high ceilings. The bed was comfortable- which is important for this tall body with a sensitive back. I highly recommend!"
United States
Marissa G.
The price is CA $92
CA $229 total
includes taxes & fees
Oct 12 - Oct 13
Downtown Luxe 2BR Loft Apt | Sleeps 8 | Walkable
A hotel room with a bed, a sofa, a chair, a small table, and a potted plant.

12. Walker`s Point Designer 2BR · Prime Location with Balcony and Gym · Sleeps 6

Walker`s Point Designer 2BR · Prime Location with Balcony and Gym · Sleeps 6
Fifth Ward
8.0 out of 10, Very good, (4 reviews)
"Excellent communication throughout the process. Great location!"
United States
James A.
The price is CA $102
CA $242 total
includes taxes & fees
Nov 2 - Nov 3
Walker`s Point Designer 2BR · Prime Location with Balcony and Gym · Sleeps 6
A modern kitchen with dark cabinets, a white stove, and a dining area with a table and chairs.

13. Upper Pro Retreat near Hospitals - 30 day min - Garage & Yard. Dog-friendly!

Upper Pro Retreat near Hospitals - 30 day min - Garage & Yard. Dog-friendly!
Fair Park
10.0 out of 10, Exceptional, (3 reviews)
"I chose this area to visit family, once again, Lorinda was the best! I will visit again soon. "
United States
AnnaLisa S.
Upper Pro Retreat near Hospitals - 30 day min - Garage & Yard. Dog-friendly!
A hotel room with a bed, a bathroom with a large mirror, a sink, and a window.

14. 1 King Bed | Non-Smoking, Kitchen

1 King Bed | Non-Smoking, Kitchen
Milwaukee WI
9.4 out of 10, Exceptional, (40 reviews)
"I’ll return for sure."
United States
William
The price is CA $108
CA $122 total
includes taxes & fees
Nov 8 - Nov 9
1 King Bed | Non-Smoking, Kitchen
A dining area with a round table, four chairs, a wooden floor, a door, and a lamp.

15. Quiet House

Quiet House
Milwaukee
7.6 out of 10, Good, (22 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 CA $96
CA $302 total
includes taxes & fees
Oct 12 - Oct 13
Quiet House
A modern kitchen with white cabinets, a stainless steel stove, and a wooden countertop.

16. Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!
Downtown Milwaukee
10.0 out of 10, Exceptional, (12 reviews)
"Nice place, close to Brady Street."
United States
Kevin M.
The price is CA $98
CA $417 total
includes taxes & fees
Oct 19 - Oct 20
Remodeled Home - Steps from Brady Street!
A spacious indoor area with a high ceiling, metal beams, and a central seating area with sofas.

17. Cream City Industrial Loft Near Fiserv with Parking | Suite 4 | Sleeps 8

Cream City Industrial Loft Near Fiserv with Parking | Suite 4 | Sleeps 8
Westown
9.4 out of 10, Exceptional, (6 reviews)
"Great location & would stay again next in town!"
United States
Mary W.
The price is CA $77
CA $204 total
includes taxes & fees
Oct 12 - Oct 13
Cream City Industrial Loft Near Fiserv with Parking | Suite 4 | Sleeps 8
A bedroom with a bed, a desk, a chair, a lamp, a ceiling fan, and a window with a sign.

18. The Nohl | A Lake Effect Stay Near Brady Street

The Nohl | A Lake Effect Stay Near Brady Street
Lower East Side
The price is CA $120
CA $372 total
includes taxes & fees
Oct 12 - Oct 13
The Nohl | A Lake Effect Stay Near Brady Street
A modern living room with a sectional sofa, a ceiling fan, large windows, and a TV.

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

Babich Building - 3 Bedroom - Upper Apt #4
West Allis
8.8 out of 10, Excellent, (8 reviews)
"Great property, but a little hot and hard to cool down."
United States
Laura
The price is CA $246
CA $578 total
includes taxes & fees
Oct 12 - Oct 13
Babich Building - 3 Bedroom - Upper Apt #4
A bedroom with a large bed, two side tables, a lamp, and a view of trees through the windows.

20. Spacious House Near American Family Field+State Fair

Spacious House Near American Family Field+State Fair
West Allis
The price is CA $334
CA $732 total
includes taxes & fees
Oct 12 - Oct 13
Spacious House Near American Family Field+State Fair
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

The Iron Horse Hotel

The Iron Horse Hotel

10/10 Excellent
"I had to check in early due to an upcoming event and the front desk staff person couldn’t have been more helpful. The room was perfect and fit the vibe of the hotel. The staff at the bar outside were attentive. I’ll definitely be back!"
Catherine 1-night trip
Posted 10 hours ago
The Iron Horse Hotel

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greendale vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greendale vacation rentals we have selected for you start as low as CA $128 per night. Entering your travel dates in the search wizard 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?

Three Bedroom Upper: This vacation home rental near Greendale is located near the beach and has a balcony, a garden, 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. Make the most of the selection of games in this rental home to help you unwind.

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 Pettit National Ice Center, 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.