Greendale Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Greendale vacation rentals

Smart TV, table tennis, 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 ￥27,086
￥52,457 total
includes taxes & fees
Feb 26 - Feb 27
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 ￥18,562
￥38,408 total
includes taxes & fees
Feb 23 - Feb 24
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 ￥28,195
￥83,316 total
includes taxes & fees
Feb 16 - Feb 17
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 ￥19,249
￥37,455 total
includes taxes & fees
Feb 18 - Feb 19
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 ￥34,373
￥86,277 total
includes taxes & fees
Feb 18 - Feb 19
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 ￥13,025
￥40,956 total
includes taxes & fees
Feb 14 - Feb 15
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 ￥19,860
￥50,742 total
includes taxes & fees
Feb 19 - Feb 20
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 ￥26,811
￥35,756 total
includes taxes & fees
Feb 18 - Feb 19
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 ￥11,033
￥30,332 total
includes taxes & fees
Mar 12 - Mar 13
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 ￥14,819
￥34,778 total
includes taxes & fees
Mar 1 - Mar 2
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 ￥8,250
￥29,540 total
includes taxes & fees
Feb 16 - Feb 17
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 ￥27,499
￥67,904 total
includes taxes & fees
Feb 18 - Feb 19
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 ￥33,686
￥80,424 total
includes taxes & fees
Feb 14 - Feb 15
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 ￥21,999
￥66,823 total
includes taxes & fees
Feb 15 - Feb 16
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 ￥7,486
￥40,886 total
includes taxes & fees
Feb 17 - Feb 18
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 ￥23,679
￥49,893 total
includes taxes & fees
Feb 27 - Feb 28
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 ￥11,769
￥23,334 total
includes taxes & fees
Mar 8 - Mar 9
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 ￥9,041
￥23,306 total
includes taxes & fees
Mar 4 - Mar 5
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 ￥30,936
￥81,865 total
includes taxes & fees
Feb 15 - Feb 16
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 ￥7,509
￥40,650 total
includes taxes & fees
Feb 16 - Feb 17
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Greendale Hotel Reviews

Hilton Milwaukee

Hilton Milwaukee

10/10 Excellent
"Clean"
Kelli 2-night trip
Posted 14 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
  • 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 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?

Wooded Hills/Indoor Pool/Hot Tub/Arcade: This vacation home rental near Greendale offers an indoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and a hot tub 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 Crystal Ridge, 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.