Greendale Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Greendale holiday rentals

Smart TV, ping pong, printers

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, (49 reviews)
"Very clean and nice home.Would definitely recommend "
United States
Glenn T.
The price is HK$1,386
HK$2,667 total
includes taxes & fees
22 Feb - 23 Feb
Historic home - walk to village center. Original features with modern updates.
Outdoor dining

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, (34 reviews)
"Great location near the beach, good kitchen, large fenced yard with lots of seating options, good communication with host"
United States
Donald N.
The price is HK$950
HK$1,965 total
includes taxes & fees
23 Feb - 24 Feb
3-bedroom vacation home just a short walk to Lake Michigan
Smart TV, books

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, (12 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.
The price is HK$1,443
HK$4,263 total
includes taxes & fees
15 Feb - 16 Feb
Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly
Exterior

Wisconsin Treehouse Getaway!

Wisconsin Treehouse Getaway!
Racine
9.6 out of 10, Exceptional, (28 reviews)
"We had a wonderful time staying here while visiting the surrounding area!"
United States
Collin C.
The price is HK$985
HK$1,916 total
includes taxes & fees
18 Feb - 19 Feb
Wisconsin Treehouse Getaway!
Fridge, microwave, oven, stovetop

Luxury Historic Home - Stellar Location

Luxury Historic Home - Stellar Location
Lower East Side
9.6 out of 10, Exceptional, (26 reviews)
"Had a very nice stay. The house was great, and the kids especially loved the game room. "
United States
Martin S.
The price is HK$1,759
HK$4,414 total
includes taxes & fees
14 Feb - 15 Feb
Luxury Historic Home - Stellar Location
Dining

King Bed - Near Froedtert - FAST WiFi

King Bed - Near Froedtert - FAST WiFi
Wauwatosa
10.0 out of 10, Exceptional, (17 reviews)
"Clean and nice location. "
United States
Jim D.
The price is HK$586
HK$1,994 total
includes taxes & fees
14 Feb - 15 Feb
King Bed - Near Froedtert - FAST WiFi
Beach nearby

Charming home w/ fire pit, walk to Lake Michigan

Charming home w/ fire pit, walk to Lake Michigan
Shorewood
10.0 out of 10, Exceptional, (35 reviews)
"Property was in excellent shape. Great location. Owner was an excellent communicator. Really nice day."
United States
Steve K.
The price is HK$1,024
HK$2,605 total
includes taxes & fees
14 Feb - 15 Feb
Charming home w/ fire pit, walk to Lake Michigan
Dining

Three bedrooms upstairs

Three bedrooms upstairs
Riverwest
9.6 out of 10, Exceptional, (79 reviews)
"Cozy place with an awesome kitchen!"
United States
Lilly I.
The price is HK$1,372
HK$1,829 total
includes taxes & fees
18 Feb - 19 Feb
Three bedrooms upstairs
Room

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, (7 reviews)
"Charming apartment, convenient location"
United States
Ashton G.
The price is HK$563
HK$1,547 total
includes taxes & fees
12 Mar - 13 Mar
KK lower · Funky 2BR in Prime Bay View - w/ Parking
Dining

Potter Lower · Funky 2.5BR in the Heart of Bay View - w/ Parking

Potter Lower · Funky 2.5BR in the Heart of Bay View - w/ Parking
Bay View
9.2 out of 10, Wonderful, (16 reviews)
"The property is extraordinarily charming and was perfect for a short family visit in mid/late September. It's close to Bayview and is generally a good location for having fun in Milwaukee.I'm bookmarking this place for future visits with family and friends."
United States
Alexander H.
The price is HK$758
HK$1,779 total
includes taxes & fees
1 Mar - 2 Mar
Potter Lower · Funky 2.5BR in the Heart of Bay View - w/ Parking
Dining

Quiet House

Quiet House
Milwaukee
7.6 out of 10, Good, (8 reviews)
"Very relaxing and peaceful "
United States
Laterrance G.
The price is HK$422
HK$1,511 total
includes taxes & fees
23 Feb - 24 Feb
Quiet House
Smart TV, books, music library, stereo

Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer

Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer
Bay View
10.0 out of 10, Exceptional, (27 reviews)
"We were overall very impressed "
United States
Ethan N.
The price is HK$1,407
HK$3,474 total
includes taxes & fees
23 Feb - 24 Feb
Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer
Dining

Style and Luxury - Unbeatable Location

Style and Luxury - Unbeatable Location
Lower East Side
9.6 out of 10, Exceptional, (13 reviews)
"Great location!"
United States
Mike G.
The price is HK$1,724
HK$4,115 total
includes taxes & fees
14 Feb - 15 Feb
Style and Luxury - Unbeatable Location
Interior

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

Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions
Lower East Side
9.8 out of 10, Exceptional, (23 reviews)
"Great property for our family group for a long weekend in Milwaukee. "
United States
Karl S.
The price is HK$1,125
HK$3,446 total
includes taxes & fees
17 Feb - 18 Feb
Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions
TV

Tucked Away Off Brady - 4 Beds

Tucked Away Off Brady - 4 Beds
Downtown Milwaukee
9.0 out of 10, Wonderful, (19 reviews)
"The place was spotless when we arrived and it had everything we needed for a comfortable stay. It was in a great location with lots to do."
United States
Ben K.
The price is HK$383
HK$2,092 total
includes taxes & fees
17 Feb - 18 Feb
Tucked Away Off Brady - 4 Beds
Outdoor dining

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Johnson Woods
9.8 out of 10, Exceptional, (27 reviews)
"We stayed while attending the WI state fair. Quiet and safe neighborhood and really close to the fairgrounds. House was clean and easy to get to. We enjoyed our stay and the fenced in backyard was perfect for our Frenchie. "
United States
Roy W.
The price is HK$1,243
HK$2,589 total
includes taxes & fees
1 Mar - 2 Mar
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Dining

East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge

East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge
Downtown Milwaukee
10.0 out of 10, Exceptional, (1 review)
"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.
The price is HK$600
HK$1,190 total
includes taxes & fees
8 Mar - 9 Mar
East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge
Private kitchen

2BR apt w/ laundry + parking

2BR apt w/ laundry + parking
Murray Hill
10.0 out of 10, Exceptional, (12 reviews)
"The apartment is clean, spacious and close to the activities we were in town for."
United States
Kelly S.
The price is HK$461
HK$1,189 total
includes taxes & fees
4 Mar - 5 Mar
2BR apt w/ laundry + parking
Fridge, microwave, oven, stovetop

Stunning Upscale Retreat - Steps From Everything

Stunning Upscale Retreat - Steps From Everything
Lower East Side
9.8 out of 10, Exceptional, (31 reviews)
"It was a great place and close to Brady street! Definitely recommend. "
United States
Hugh L.
The price is HK$1,583
HK$4,189 total
includes taxes & fees
15 Feb - 16 Feb
Stunning Upscale Retreat - Steps From Everything
TV, video games

Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!
Downtown Milwaukee
9.8 out of 10, Exceptional, (6 reviews)
"Enjoyed stay at this nice home "
United States
Eduardo P.
The price is HK$383
HK$2,074 total
includes taxes & fees
16 Feb - 17 Feb
Remodeled Home - Steps from Brady Street!
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

Hilton Milwaukee

Hilton Milwaukee

10/10 Excellent
"Clean"
Kelli 2-night trip
Posted 18 hours ago
Hilton Milwaukee

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
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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?

Wooded Hills/Indoor Pool/Hot Tub/Arcade: 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. It offers a balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday.

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.