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Compare 395 Vacation Homes in Greendale with updated reviews, rates, and availability.

Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

10.0 out of 10, Exceptional, (321)
"Great house for being in the lake. Has a nice backyard that is fenced in and was perfect for our dogs. "
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

10.0 out of 10, Exceptional, (14)
"The property was a good place to stay at! I will say it was what we needed for everyone to stay and have a place to sleep. The only issue with was trying to fit a vehicle in the garage. We took my friends Tahoe and it was a tough spot to fit in the garage, which we can tell it’s meant for smaller vehicles. And there were a pair of eyelashes set out on the coffee table. But overall for anyone with a bigger family or group of friends that need somewhere to stay I would recommend this location!"
The price is AED 735
AED 1,970 total
includes taxes & fees
25 Nov - 26 Nov
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

Amazing Five Bedroom Milwaukee Vacation Home!!

10.0 out of 10, Exceptional, (37)
"Went for our annual golf trip. Perfect house for the 6 of us. Never had to leave the house after our rounds!"
Amazing Five Bedroom Milwaukee Vacation Home!!

Booth Upper · Amazing view, Modern Space

10.0 out of 10, Exceptional, (35)
"Loved everything about this place. Spacious, nice, well stocked, great view of the city. Really liked how it was close enough to the city to get there in 10 minutes, but far enough to have some quiet and privacy. Not sure if I’ll ever visit Milwaukee again but I will definitely look for this place again if I do."
Booth Upper · Amazing view, Modern Space

Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan

9.8 out of 10, Exceptional, (62)
"Property owner was great to deal with, and communication was also very good. The neighborhood was quiet, and there is a nice bar/restaurant directly next door. All amenties were exactly as described."
Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan

NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a lovely stay in this home. The unit is part of a duplex, with accommodations in the upstairs of the house. We had three kids (ages 6 to 2) with us, and we were all big fans of the unit! The kids loved the bunk beds, the master suite was very spacious, the kitchen well-stocked with cooking tools (though we mostly ate out), and entertainment was aplenty with board games and even a foosball/air hockey/ping pong table included. We were walking distance to Brady Street and the...
The price is AED 558
AED 1,646 total
includes taxes & fees
10 Dec - 11 Dec
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

Beautiful Waukesha Home

10.0 out of 10, Exceptional, (21)
"Beautiful home in a quiet neighborhood. Very clean property with all the amenities needed for our son’s wedding weekend. Host was very responsive and accommodating. Would definitely stay again if in the area. "
The price is AED 918
AED 1,984 total
includes taxes & fees
1 Dec - 2 Dec
Beautiful Waukesha Home

Large, Private 3 Br Home | Ideal Location

9.6 out of 10, Exceptional, (32)
"This home has only one flaw, the city of Milwaukee has corrupt leaders and crime is high. We enjoyed the open layout with plenty of seating. The beds are comfy and water pressure in the shower, fantastic. We were sad to come out to our car window busted out in the morning."
The price is AED 841
AED 1,458 total
includes taxes & fees
6 Dec - 7 Dec
Large, Private 3 Br Home | Ideal Location

Tichigan Lake House - Pontoon Boat & Fire Pit - Dog Friendly - Newly Renovated

10.0 out of 10, Exceptional, (5)
"The place was great. Beautiful location. Relaxing environment. Convenience amenities. We really enjoyed the kayaks and the fire pit. Gorgeous sunrises and sunsets. Would highly recommend!"
The price is AED 618
AED 1,332 total
includes taxes & fees
25 Nov - 26 Nov
Tichigan Lake House - Pontoon Boat & Fire Pit - Dog Friendly - Newly Renovated

Heated Pool, Hot Tub, Fishing Pond, Game Room, Events!! Fall Discounts! Weddings

9.8 out of 10, Exceptional, (193)
"Me and 9 of my friends rented this space it was very affordable for all the amenities that it came with. Robert was very responsive to messaging before and during our stay. The property is huge and built for all kinds of activities. Can’t wait to book again! "
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events!! Fall Discounts! Weddings

Spacious Pewaukee Lake/ Pier Access Home

8.6 out of 10, Excellent, (11)
"Our company needed to send workers out of town to a job site in the Delafield area. The house was perfect for our needs, close to the job site and enough beds for each person. That is always our struggle, enough beds, they will share a room but not a bed. Our employees enjoyed being able to sit out after a long day and sit around the fire pit and relax. Steve was great to work with, as we needed to book an additional week and despite having availability VRBO site showed it unavailable. We...
Spacious Pewaukee Lake/ Pier Access Home

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

9.8 out of 10, Exceptional, (16)
"This house was the perfect place for a quick girls weekend getaway!! It was clean and quiet and in a perfect location. "
The price is AED 393
AED 970 total
includes taxes & fees
3 Dec - 4 Dec
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

Downtown Bayview, 2 miles from downtown Milwaukee

9.4 out of 10, Exceptional, (124)
"Great location, house was clean, worked for what we needed. Keep in mind - a bit bare bones ) ie no soap or shampoo, coffee, etc) - just a place to stay. Would stay here again if I needed to stay in BayView."
Downtown Bayview, 2 miles from downtown Milwaukee

Historic, Vintage, Classy, 11 bed, 5+ bath!

10.0 out of 10, Exceptional, (6)
" We were immediately impressed with the property! It was beautiful and well appointed.The host was responsive."
Historic, Vintage, Classy, 11 bed, 5+ bath!

Large Groups - KING Bed - 3 Blocks to Restaurants

10.0 out of 10, Exceptional, (14)
"Everything was great!"
Large Groups - KING Bed - 3 Blocks to Restaurants

MKE Riverwest Retreat - Newly Renovated

10.0 out of 10, Exceptional, (2)
"Firstly the host made this stay a breeze! Host communicated with me for the booking process, gave plenty of information regarding the area and the house, and had the listing for a fair price. The house itself is awesome! Selection of games was great especially for our group (we play a lot of board and card games), the TV in the living room was quality, the entire house was spotless when we arrived. Everything in the house was too notch condition, great kitchen, everything was well labeled and...
MKE Riverwest Retreat - Newly Renovated

3-bedroom vacation home just a short walk to Lake Michigan

9.6 out of 10, Exceptional, (10)
"Wonderful little house with view of North Beach and access to everything. A perfect location for beach glass pickers to run up and down the lakeshore, beautiful parks and beaches as well as shopping, craft fairs, Milwaukee, outlet malls and the airport. Highly recommend. "
3-bedroom vacation home just a short walk to Lake Michigan

Cozy Lofted Riverwest Apartment

7.6 out of 10, Good, (11)
"Would stay here again"
Cozy Lofted Riverwest Apartment

Close to airport and downtown Milwaukee!

10.0 out of 10, Exceptional, (80)
"Our stay was excellent! Everything went smoothly and we would definitely stay here again. The property was exactly as described online. "
Close to airport and downtown Milwaukee!

Renovated 2-bed flat w/patio in heart of Bay View

9.6 out of 10, Exceptional, (9)
"Great location and within walking distance of everything in Bayview. "
Renovated 2-bed flat w/patio in heart of Bay View
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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Other property types in Greendale

The Plaza Hotel

3.0 star property
8.6 out of 10, Excellent, (1050)
"Cool little hotel! Old style building but clean and well maintained! Really great, quiet stay!!"
The price is AED 587
AED 692 total
includes taxes & fees
1 Dec - 2 Dec
The Plaza Hotel

Kasa Westown Milwaukee

4.0 star property
9.0 out of 10, Wonderful, (64)
"Loved it very clean and beautiful room most definitely coming back"
The price is AED 185
AED 365 total
includes taxes & fees
1 Dec - 2 Dec
Kasa Westown Milwaukee

Heated Pool, Hot Tub, Fishing Pond, Game Room, Events!! Fall Discounts! Weddings

9.8 out of 10, Exceptional, (193)
"Me and 9 of my friends rented this space it was very affordable for all the amenities that it came with. Robert was very responsive to messaging before and during our stay. The property is huge and built for all kinds of activities. Can’t wait to book again! "
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events!! Fall Discounts! Weddings
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.