Greendale Vacation Rentals

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Vacation Rentals in Greendale

Aparthotel in Downtown Milwaukee

3.0 star property
8.8 out of 10, Excellent, (1153)
"Loved this hotel! Clean friendly and cute!!"
United States
Sharon H
$168 nightly
The price is $199
Dec 2 - Dec 3
Total with taxes and fees
The Plaza Hotel

Aparthotel in Westown

4.0 star property
9.0 out of 10, Wonderful, (117)
"Perfect location, so many things were within walking distance. Also felt very safe and more convenient than a hotel room. "
United States
Kaylee
$177 nightly
The price is $209
Nov 26 - Nov 27
Total with taxes and fees
Kasa Westown Milwaukee

Apartment in Westown

4.0 star property
8.8 out of 10, Excellent, (10)
"Loved the uniqueness, location and cleanliness of the unit."
United States
Teresa
$139 nightly
The price is $164
Nov 30 - Dec 1
Total with taxes and fees
ROVE LIVING/KL - Malt House

Vacation Home in New Berlin

8.4 out of 10, Very Good, (8)
"We had an excellent family vacation at The Garden of Eden!!"
United States
Cheryl S.
$1,997 nightly
The price is $2,256
Dec 3 - Dec 4
Total with taxes and fees
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

Vacation Home in Caledonia

9.8 out of 10, Exceptional, (213)
"I want to move in. We had 13 guys for a bachelor retreat and this place was perfect. Plenty of room for us all and plenty to do. We expected to spend plenty of time exploring Milwaukee, but found ourselves hanging out at the pool or fishing in the pond when we weren’t relaxing in the game room. 10/10 would recommend!"
United States
Caleb B.
$657 nightly
The price is $693
Dec 21 - Dec 22
Total with taxes and fees
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

Vacation Home in Sussex

9.8 out of 10, Exceptional, (50)
"Wonderful property. Host was extremely responsive and helpful."
United States
joan r.
Wooded Hills/Indoor Pool/Hot Tub/Arcade

Apartment in Lower East Side

3.0 star property
7.6 out of 10, Good, (7)
"Our stay was great. The property was at it was described and expected. The owner was available via text and communicated with me when I had questions. We would stay again!"
United States
Vera
ROVE LIVING/KB - Prospect

Condo in Downtown Milwaukee

9.0 out of 10, Wonderful, (46)
"Walking distance to several great bars, restaurants, breweries and the summer fest area. We really enjoyed our stay!"
United States
SCOTT T.
$280 nightly
The price is $330
Nov 26 - Nov 27
Total with taxes and fees
Downtown Eastside gem near Fiserv Forum Water St Brady St

Vacation Home in River Hills

10.0 out of 10, Exceptional, (3)
"Love the indoor pool and the movie room!"
United States
JOE C.
Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!

Vacation Home in Lower East Side

9.8 out of 10, Exceptional, (31)
"It was a great place and close to Brady street! Definitely recommend. "
United States
Hugh L.
$455 nightly
The price is $536
Nov 30 - Dec 1
Total with taxes and fees
Stunning Upscale Retreat - Steps From Everything

Vacation Home in Bay View

9.6 out of 10, Exceptional, (8)
"Great place!"
United States
Kathy R.
$393 nightly
The price is $463
Dec 2 - Dec 3
Total with taxes and fees
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

Vacation Home in Riverwest

9.6 out of 10, Exceptional, (76)
"He was very kind!"
United States
Hope
$199 nightly
The price is $234
Nov 30 - Dec 1
Total with taxes and fees
Three bedrooms upstairs

Vacation Home in Johnson Woods

9.8 out of 10, Exceptional, (26)
"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.
$254 nightly
The price is $299
Nov 30 - Dec 1
Total with taxes and fees
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

Vacation Home in Burnham Park

9.6 out of 10, Exceptional, (252)
"Easy access, enjoyed the history, had everything we needed"
United States
Derrick G.
Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10

Cabin in Racine

9.8 out of 10, Exceptional, (27)
"Such a cute place to stay at! Perfect location for visiting Racine. Kitchen was a great size and WiFi worked well too! Highly recommend staying here "
United States
Meghan S.
Rustic Riverside A-Frame Retreat: Secluded Charm.

Vacation Home in Waukesha

9.8 out of 10, Exceptional, (15)
"Awesome place - would definitely stay again! "
United States
Anonymous traveler
Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

Vacation Home in Waukesha

10.0 out of 10, Exceptional, (15)
"Will come and stay again great host and home"
United States
Dion S.
$269 nightly
The price is $304
Nov 30 - Dec 1
Total with taxes and fees
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Vacation Home in Downtown Milwaukee

9.6 out of 10, Exceptional, (23)
"Great house - big group I stayed with loved it and tons of places to sleep and hang out. Fantastic location by the water and near some good restaurants. Hosts were super responsive. "
United States
Henri E.
$1,484 nightly
The price is $1,673
Dec 21 - Dec 22
Total with taxes and fees
MKE Mansion - Both Wings

Vacation Home in Lower East Side

9.6 out of 10, Exceptional, (64)
"It was clean and close to our wedding venue. "
United States
Kathy H.
$370 nightly
The price is $436
Dec 1 - Dec 2
Total with taxes and fees
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

Vacation Home in Downtown Milwaukee

10.0 out of 10, Exceptional, (4)
"Enjoyed stay at this nice home "
United States
Eduardo P.
$225 nightly
The price is $265
Nov 30 - Dec 1
Total with taxes and fees
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

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Greendale in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $164 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18: 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 7 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 selection of games 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.