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
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

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, (52 reviews)
"Very clean and nice home.Would definitely recommend "
United States
Glenn T.
The price is ￥28,145
￥53,989 total
includes taxes & fees
May 19 - May 20
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 ￥21,430
￥40,193 total
includes taxes & fees
May 25 - May 26
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 ￥21,430
￥35,169 total
includes taxes & fees
May 22 - May 23
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 ￥23,811
￥38,183 total
includes taxes & fees
May 22 - May 23
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 ￥17,144
￥37,656 total
includes taxes & fees
May 19 - May 20
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, (30 reviews)
"Beautiful atmosphere "
United States
Stephanie
The price is ￥20,001
￥39,278 total
includes taxes & fees
May 19 - May 20
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 ￥36,574
￥78,446 total
includes taxes & fees
May 19 - May 20
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 ￥21,747
￥54,106 total
includes taxes & fees
Jun 10 - Jun 11
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 ￥7,778
￥41,923 total
includes taxes & fees
May 25 - May 26
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, (10 reviews)
"Our son and his groomsmen stayed here for his wedding weekend. Great accommodations!"
United States
Kathy C.
The price is ￥27,537
￥59,209 total
includes taxes & fees
May 19 - May 20
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 ￥25,573
￥33,894 total
includes taxes & fees
May 19 - May 20
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 ￥7,778
￥41,736 total
includes taxes & fees
May 25 - May 26
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 ￥22,859
￥69,435 total
includes taxes & fees
May 20 - May 21
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 ￥24,763
￥46,814 total
includes taxes & fees
May 19 - May 20
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 ￥30,848
￥88,587 total
includes taxes & fees
May 26 - May 27
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 ￥78,576
￥113,713 total
includes taxes & fees
May 26 - May 27
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 ￥44,288
￥89,905 total
includes taxes & fees
Jun 13 - Jun 14
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 ￥9,524
￥21,101 total
includes taxes & fees
May 19 - May 20
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 ￥12,623
￥27,408 total
includes taxes & fees
Jun 9 - Jun 10
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 ￥28,573
￥70,557 total
includes taxes & fees
May 19 - May 20
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.
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

Embassy Suites by Hilton Milwaukee Brookfield

Embassy Suites by Hilton Milwaukee Brookfield

10/10 Excellent
"The hotel was excellent! The staff was friendly and helpful! The breakfast was very good!"
Ronald 1-night trip
Posted 2 hours ago
Embassy Suites by Hilton Milwaukee Brookfield

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?

Quiet House: This vacation home rental near Greendale offers a fireplace, a selection of games, and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 Milwaukee County Zoo, 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.