Search Vacation Homes in Greendale

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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)
"Great location and wonderful house. Great location for family with small kids. Parks are super close, downtown street is wonderful to eat and drink. Host is super helpful and responsive. "
United States
Patrick J.
$313 nightly
The price is $341
Dec 24 - Dec 25
Total with taxes and fees
Historic home - walk to village center. Original features with modern updates.

KK lower · Funky 2BR in Prime Bay View - w/ Parking

KK lower · Funky 2BR in Prime Bay View - w/ Parking
Bay View
10.0 out of 10, Exceptional, (7)
"Charming apartment, convenient location"
United States
Ashton G.
$195 nightly
The price is $199
Jan 13 - Jan 14, 2026
Total with taxes and fees
KK lower · Funky 2BR in Prime Bay View - w/ Parking

Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!
Downtown Milwaukee
10.0 out of 10, Exceptional, (5)
"Enjoyed stay at this nice home "
United States
Eduardo P.
$229 nightly
The price is $270
Jan 12 - Jan 13, 2026
Total with taxes and fees
Remodeled Home - Steps from Brady Street!

Peaceful East Side-2 min UWM-Dining-Coffee-Parking

Peaceful East Side-2 min UWM-Dining-Coffee-Parking
Upper East Side
10.0 out of 10, Exceptional, (5)
"Great property and a great location. Lulu was an incredible and thoughtful host. "
United States
Lori B.
$241 nightly
The price is $284
Dec 27 - Dec 28
Total with taxes and fees
Peaceful East Side-2 min UWM-Dining-Coffee-Parking

Exclusive Brownstone Residence

Exclusive Brownstone Residence
2.0 star property
Halyard Park
10.0 out of 10, Exceptional, (1)
"We had a nice stay at this property and hope to do it again "
United States
Damien S.
$190 nightly
The price is $224
Dec 24 - Dec 25
Total with taxes and fees
Exclusive Brownstone Residence

Vibrant Milwaukee Townhome near Downtown

Vibrant Milwaukee Townhome near Downtown
Riverwest
8.0 out of 10, Very Good, (2)
"This is a cool, fun neighborhood! It’s really central to pretty much everything and close to downtown. The property is cozy and is a nice place to hang out. We had a wonderful time! "
United States
Thomas S.
$222 nightly
The price is $261
Jan 2 - Jan 3, 2026
Total with taxes and fees
Vibrant Milwaukee Townhome near Downtown

Rare East Side-2 min walk to UWM-Garage-Lake Mich

Rare East Side-2 min walk to UWM-Garage-Lake Mich
Upper East Side
10.0 out of 10, Exceptional, (2)
"Loved our stay. Nice clean place that was well stocked."
United States
Patty S.
$241 nightly
The price is $284
Jan 7 - Jan 8, 2026
Total with taxes and fees
Rare East Side-2 min walk to UWM-Garage-Lake Mich

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

3Kings, Renovated, FenceYard, Games, Ctr Loc - WEEKLY STAY DEALS

3Kings, Renovated, FenceYard, Games, Ctr Loc - WEEKLY STAY DEALS
Riverwest
10.0 out of 10, Exceptional, (14)
"Great place to stay. My family enjoyed our time there. Exceptionaly clean, great communication from the host, could not ask for more. Would most definitely stay again here next time my travels take me through the area! "
United States
Mitchell D.
$333 nightly
The price is $393
Jan 20 - Jan 21, 2026
Total with taxes and fees
3Kings, Renovated, FenceYard, Games, Ctr Loc - WEEKLY STAY DEALS

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, (34)
"Great location near the beach, good kitchen, large fenced yard with lots of seating options, good communication with host"
United States
Donald N.
$222 nightly
The price is $251
Jan 20 - Jan 21, 2026
Total with taxes and fees
3-bedroom vacation home just a short walk to Lake Michigan

Whole House in Bay View + Fenced-in Yard + Parking

Whole House in Bay View + Fenced-in Yard + Parking
Bay View
10.0 out of 10, Exceptional, (11)
"was great and close to our daughter"
United States
Nicholas S.
$338 nightly
The price is $399
Dec 29 - Dec 30
Total with taxes and fees
Whole House in Bay View + Fenced-in Yard + Parking

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

NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
2.0 star property
Lower East Side
9.8 out of 10, Exceptional, (20)
"Great property for our family group for a long weekend in Milwaukee. "
United States
Karl S.
$360 nightly
The price is $425
Jan 19 - Jan 20, 2026
Total with taxes and fees
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer

Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer
2.0 star property
Bay View
10.0 out of 10, Exceptional, (27)
"Very comfortable and convenient to everything downtown."
United States
Reddemann R.
$355 nightly
The price is $419
Dec 23 - Dec 24
Total with taxes and fees
Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer

Relax in Style: 4BR Milwaukee Home ¦ Family-Friendly ¦ Warm & Cozy

Relax in Style: 4BR Milwaukee Home ¦ Family-Friendly ¦ Warm & Cozy
Upper East Side
9.2 out of 10, Wonderful, (5)
$337 nightly
The price is $344
Dec 23 - Dec 24
Total with taxes and fees
Relax in Style: 4BR Milwaukee Home ¦ Family-Friendly ¦ Warm & Cozy

Quiet House

Quiet House
Milwaukee
6.8 out of 10, (6)
"Great stay for attending Summerfest. Short trip to the festival. Place was tidy and comfortable."
United States
Kerry N.
$164 nightly
The price is $193
Dec 23 - Dec 24
Total with taxes and fees
Quiet House

Whole House in Walker's Point

Whole House in Walker's Point
Fifth Ward
10.0 out of 10, Exceptional, (1)
$397 nightly
The price is $468
Dec 27 - Dec 28
Total with taxes and fees
Whole House in Walker's Point

Lake Effect Club | The Nohl

Lake Effect Club | The Nohl
2.0 star property
Lower East Side
$201 nightly
The price is $237
Dec 28 - Dec 29
Total with taxes and fees
Lake Effect Club | The Nohl

2bed 1.5bath House, Lower Eastside, King Bed, Fire Pit, Sleeps 6

2bed 1.5bath House, Lower Eastside, King Bed, Fire Pit, Sleeps 6
Downtown Milwaukee
10.0 out of 10, Exceptional, (1)
"Overall had the best stay with me and my 3 kids! The house was even better than the pictures. Cute decor, comfy beds, great kitchen amenities to make your stay feel right at home. The host provided clear, easy house and parking instructions! And a grocery store is a close, 5 minute for easy shopping trips. "
United States
Kristen M.
$253 nightly
The price is $298
Dec 23 - Dec 24
Total with taxes and fees
2bed 1.5bath House, Lower Eastside, King Bed, Fire Pit, Sleeps 6

Lake Effect Club | The Sidney

Lake Effect Club | The Sidney
2.0 star property
Lower East Side
$222 nightly
The price is $261
Jan 4 - Jan 5, 2026
Total with taxes and fees
Lake Effect Club | The Sidney

Stylish Home - Walk to Brady St - Sleeps 7 + Pets

Stylish Home - Walk to Brady St - Sleeps 7 + Pets
2.0 star property
Lower East Side
$254 nightly
The price is $300
Jan 8 - Jan 9, 2026
Total with taxes and fees
Stylish Home - Walk to Brady St - Sleeps 7 + Pets
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

Greendale Vacation Homes information

Number of reviews
178
Accommodation
474 Vacation Homes
Lowest Price
$174
Highest Price
$468

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