Greendale Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

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, (52 reviews)
"Very clean and nice home.Would definitely recommend "
United States
Glenn T.
The price is HK$1,388
HK$2,637 total
includes taxes & fees
20 May - 21 May
Historic home - walk to village center. Original features with modern updates.
Marina

Irish Mist V @ Reefpoint Marina

Irish Mist V @ Reefpoint Marina
Racine
9.8 out of 10, Exceptional, (30 reviews)
"Nice spot to stay a night!"
United States
Joseph P.
The price is HK$1,057
HK$1,983 total
includes taxes & fees
28 May - 29 May
Irish Mist V @ Reefpoint Marina
Outdoor dining

Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19

Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
Racine
9.4 out of 10, Exceptional, (15 reviews)
"A great adventure at the boat, a great hot tub, and a very clean pool, a wonderful location, very great view."
United States
Bogdan S.
The price is HK$1,057
HK$1,735 total
includes taxes & fees
22 May - 23 May
Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
Outdoor pool, a heated pool

Marina Life II - 28 Carver @ Reef Point Marina

Marina Life II - 28 Carver @ Reef Point Marina
Racine
9.6 out of 10, Exceptional, (48 reviews)
"Fantastic boat stay. This is the second time we’ve stayed with Patrick and it’s been our favorite so far. Boat is immaculate and roomy for two. We really love the location as there’s always something going on at the marina or downtown. Within walking distance to whatever you need. It’s also very reasonable to stay here versus a hotel. One of our favorite places!!! "
United States
Jason D.
The price is HK$1,174
HK$1,883 total
includes taxes & fees
22 May - 23 May
Marina Life II - 28 Carver @ Reef Point Marina
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, (35 reviews)
"Convenient location, comfortable house, thoughtful amenities, easy walk to lake, quick drive for food and various activities. "
United States
Beth S.
The price is HK$846
HK$1,857 total
includes taxes & fees
21 May - 22 May
3-bedroom vacation home just a short walk to Lake Michigan
Exterior

Wisconsin Treehouse Getaway!

Wisconsin Treehouse Getaway!
Racine
9.6 out of 10, Exceptional, (29 reviews)
"Beautiful atmosphere "
United States
Stephanie
The price is HK$987
HK$1,938 total
includes taxes & fees
19 May - 20 May
Wisconsin Treehouse Getaway!
Living area

Serene 4-bedroom house with brook and forest in charming Racine

Serene 4-bedroom house with brook and forest in charming Racine
Racine
The price is HK$1,804
HK$3,869 total
includes taxes & fees
18 May - 19 May
Serene 4-bedroom house with brook and forest in charming Racine
Beach nearby

Charming home w/ fire pit, walk to Lake Michigan

Charming home w/ fire pit, walk to Lake Michigan
Shorewood
9.8 out of 10, Exceptional, (39 reviews)
"Host communication was excellent. House was clean and perfect for a little weekend getaway!"
United States
Grayson P.
The price is HK$1,018
HK$2,592 total
includes taxes & fees
17 May - 18 May
Charming home w/ fire pit, walk to Lake Michigan
TV

Tucked Away Off Brady - 4 Beds

Tucked Away Off Brady - 4 Beds
Downtown Milwaukee
9.2 out of 10, Wonderful, (23 reviews)
"Great location near Brady street. Walkable to lots of shops, bars, restaurants."
United States
Andrea M.
The price is HK$384
HK$2,059 total
includes taxes & fees
18 May - 19 May
Tucked Away Off Brady - 4 Beds
Smart TV, books

Sunny & Spacious 4BR East Side Stay ¦ Balcony ¦ Family-Friendly

Sunny & Spacious 4BR East Side Stay ¦ Balcony ¦ Family-Friendly
Upper East Side
9.4 out of 10, Exceptional, (9 reviews)
"Our son and his groomsmen stayed here for his wedding weekend. Great accommodations!"
United States
Kathy C.
The price is HK$1,359
HK$2,921 total
includes taxes & fees
19 May - 20 May
Sunny & Spacious 4BR East Side Stay ¦ Balcony ¦ Family-Friendly
Dining

Three bedrooms upstairs

Three bedrooms upstairs
Riverwest
9.6 out of 10, Exceptional, (90 reviews)
"Great place!! So much room and a great location. Host was communicative and check in process was smooth. We would happily stay here again! And if you like to cook, this kitchen is completely stocked with everything you would need"
United States
Carrie
The price is HK$1,262
HK$1,682 total
includes taxes & fees
17 May - 18 May
Three bedrooms upstairs
Fridge, microwave, oven, stovetop

Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!
Downtown Milwaukee
9.8 out of 10, Exceptional, (8 reviews)
"Enjoyed stay at this nice home "
United States
Eduardo P.
The price is HK$384
HK$2,059 total
includes taxes & fees
18 May - 19 May
Remodeled Home - Steps from Brady Street!
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, (30 reviews)
"Great location, slept 6 comfortably."
United States
Carolyn C.
The price is HK$1,381
HK$3,761 total
includes taxes & fees
17 May - 18 May
Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions
TV

KK Upper · 2BR Sunny Upper in Prime Bay View - w/ Parking

KK Upper · 2BR Sunny Upper in Prime Bay View - w/ Parking
Bay View
9.8 out of 10, Exceptional, (12 reviews)
"Super easy check in and out and great location. Would stay again!"
United States
Katie T.
The price is HK$1,206
HK$2,285 total
includes taxes & fees
17 May - 18 May
KK Upper · 2BR Sunny Upper in Prime Bay View - w/ Parking
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, (15 reviews)
"Beautiful house, excellent location, attentive host! It was a great stay! "
United States
Cary W.
The price is HK$1,506
HK$4,342 total
includes taxes & fees
18 May - 19 May
Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly
Smart TV, fireplace

Lake Michigan Waterfront Designer Villa

Lake Michigan Waterfront Designer Villa
Racine
9.8 out of 10, Exceptional, (16 reviews)
"The view of Lake Michigan was incredible. Had an amazing "
United States
Lauren O.
The price is HK$4,306
HK$6,129 total
includes taxes & fees
1 Jun - 2 Jun
Lake Michigan Waterfront Designer Villa
Fridge, microwave, oven, stovetop

Historic house on tree lined red brick street of historic homes.

Historic house on tree lined red brick street of historic homes.
Racine
10.0 out of 10, Exceptional, (41 reviews)
"Beautiful location and plenty of room for our group for the weekend!"
United States
DaTablegaming G.
The price is HK$2,185
HK$4,436 total
includes taxes & fees
13 Jun - 14 Jun
Historic house on tree lined red brick street of historic homes.
Dining

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, (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$1,410
HK$2,188 total
includes taxes & fees
15 Jun - 16 Jun
East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge | Sleeps 4
Interior

Cream City Industrial Loft Near Fiserv with Parking | Suite 1 | Sleeps 8

Cream City Industrial Loft Near Fiserv with Parking | Suite 1 | Sleeps 8
Westown
8.6 out of 10, Excellent, (10 reviews)
"Beautiful building extremely clean, would come again "
United States
Abdirahman
The price is HK$421
HK$1,120 total
includes taxes & fees
17 May - 18 May
Cream City Industrial Loft Near Fiserv with Parking | Suite 1 | Sleeps 8
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, (30 reviews)
"This was our second time staying here and I can’t recommend it enough! The owners are so thoughtful and have left little treats or things for us each time we’ve stayed. They have everything you might need and then some, making it feel like home away from home. We will definitely stay here again. "
United States
Amber T.
The price is HK$1,409
HK$3,480 total
includes taxes & fees
8 Jun - 9 Jun
Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer
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

Country Inn & Suites By Radisson, Brown Deer - Milwaukee North

Country Inn & Suites By Radisson, Brown Deer - Milwaukee North

10/10 Excellent
"Breakfast was great "
Larry 1-night trip
Posted 8 hours ago
Country Inn & Suites By Radisson, Brown Deer - Milwaukee North

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?

Three bedrooms upstairs : This holiday home rental outside of Greendale offers a balcony, a garden and a BBQ to help you feel perfectly comfortable 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. Make the most of games in this rental home to help you unwind.

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 Milwaukee County Zoo, 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.