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Our top choices for Greendale vacation homes

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, (48)
$313 nightly
The price is $341
Dec 24 - Dec 25
Total with taxes and fees

KK lower · Funky 2BR in Prime Bay View - w/ Parking
KK lower · Funky 2BR in Prime Bay View - w/ ParkingBay View
10.0 out of 10, Exceptional, (7)
$195 nightly
The price is $199
Jan 13 - Jan 14, 2026
Total with taxes and fees

Remodeled Home - Steps from Brady Street!
Remodeled Home - Steps from Brady Street!Downtown Milwaukee
10.0 out of 10, Exceptional, (5)
$229 nightly
The price is $270
Jan 12 - Jan 13, 2026
Total with taxes and fees

Peaceful East Side-2 min UWM-Dining-Coffee-Parking
Peaceful East Side-2 min UWM-Dining-Coffee-ParkingUpper East Side
10.0 out of 10, Exceptional, (5)
$241 nightly
The price is $284
Dec 27 - Dec 28
Total with taxes and fees

10.0 out of 10, Exceptional, (1)
$190 nightly
The price is $224
Dec 24 - Dec 25
Total with taxes and fees

Vibrant Milwaukee Townhome near Downtown
Vibrant Milwaukee Townhome near DowntownRiverwest
8.0 out of 10, Very Good, (2)
$222 nightly
The price is $261
Jan 2 - Jan 3, 2026
Total with taxes and fees

Rare East Side-2 min walk to UWM-Garage-Lake Mich
Rare East Side-2 min walk to UWM-Garage-Lake MichUpper East Side
10.0 out of 10, Exceptional, (2)
$241 nightly
The price is $284
Jan 7 - Jan 8, 2026
Total with taxes and fees

Potter Upper · Bright 1.5BR in the Heart of Bay View - w/ Parking
Potter Upper · Bright 1.5BR in the Heart of Bay View - w/ ParkingBay View
10.0 out of 10, Exceptional, (6)
$170 nightly
The price is $174
Jan 21 - Jan 22, 2026
Total with taxes and fees
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

Aloft Milwaukee Downtown
10/10 Excellent
Find out more about Greendale
Greendale Vacation Homes information
Number of reviews | 178 |
|---|---|
Accommodation | 474 Vacation Homes |
Lowest Price | $174 |
Highest Price | $468 |
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