Search Greendale Cottage Accommodations

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Cottages in Greendale

Black sheep cottage! Charming 2-bedroom cottage in peaceful West Allis
2 bedrooms, iron/ironing board, travel cot, WiFi

Black sheep cottage! Charming 2-bedroom cottage in peaceful West Allis

10.0 out of 10, Exceptional, (3)
"Clean property, lots of room. Walkable area, owner nearby. Very nice place."
Black sheep cottage! Charming 2-bedroom cottage in peaceful West Allis
Cottage near Mt. Mary College
Fridge, microwave, oven, stovetop

Cottage near Mt. Mary College

2.5 star property
10.0 out of 10, Exceptional, (16)
"Conveniently located, clean, easy to check into, had everything we needed. "
Cottage near Mt. Mary College
2 Mi to Dtwn Milwaukee: Family Home w/ Yard
House (4 Bedrooms) | Interior

2 Mi to Dtwn Milwaukee: Family Home w/ Yard

3.0 star property
2 Mi to Dtwn Milwaukee: Family Home w/ Yard
Milwaukee Home < Half Mi to Lake Michigan!
House (4 Bedrooms) | Interior

Milwaukee Home < Half Mi to Lake Michigan!

3.0 star property
Milwaukee Home < Half Mi to Lake Michigan!
Milwaukee Home w/ Fire Pit ~ 8 Mi to Lake Michigan
House (2 Bedrooms) | Interior

Milwaukee Home w/ Fire Pit ~ 8 Mi to Lake Michigan

3.0 star property
Milwaukee Home w/ Fire Pit ~ 8 Mi to Lake Michigan
Private 1BR Cottage with City Views
Paper towels

Private 1BR Cottage with City Views

10.0 out of 10, Exceptional, (3)
"Wonderful cottage in a great spot. Host was very responsive. "
Private 1BR Cottage with City Views
Novel Nest Cozy Retreat
Dining

Novel Nest Cozy Retreat

Novel Nest Cozy Retreat
Milwaukee Vacation Rental: 6 Mi to City Center!
Exterior

Milwaukee Vacation Rental: 6 Mi to City Center!

3.0 star property
Milwaukee Vacation Rental: 6 Mi to City Center!
Updated Milwaukee Home, 3 Mi to Lake Michigan!
Terrace/patio

Updated Milwaukee Home, 3 Mi to Lake Michigan!

3.0 star property
Updated Milwaukee Home, 3 Mi to Lake Michigan!
Historic Brookfield Farm Home ~ 14 Mi to Milwaukee
Interior

Historic Brookfield Farm Home ~ 14 Mi to Milwaukee

3.0 star property
8.0 out of 10, Very good, (1)
"The"
Historic Brookfield Farm Home ~ 14 Mi to Milwaukee
Walk to Parks + Bunzel's Market: Milwaukee Home!
Interior

Walk to Parks + Bunzel's Market: Milwaukee Home!

3.0 star property
10.0 out of 10, Exceptional, (2)
"The property was very inviting. I was comfortable and felt like I was at home kinda. I was visiting family and they stopped by and loved the property as well. Loved everything about the house. Some times the pictures and the places do not match but they did."
Walk to Parks + Bunzel's Market: Milwaukee Home!
MKE Pleasure Paradyz - BDSM - Adult Themed Cottage
Smart TV

MKE Pleasure Paradyz - BDSM - Adult Themed Cottage

MKE Pleasure Paradyz - BDSM - Adult Themed Cottage
7 Mi to Historic Third Ward: Home in Lincoln Park!
House (3 Bedrooms) | Interior

7 Mi to Historic Third Ward: Home in Lincoln Park!

3.0 star property
7 Mi to Historic Third Ward: Home in Lincoln Park!
Updated Cabin on 7 Acres - Day Trip to Lake Geneva
House (3 Bedrooms) | Interior

Updated Cabin on 7 Acres - Day Trip to Lake Geneva

3.0 star property
Updated Cabin on 7 Acres - Day Trip to Lake Geneva
Pet-friendly Home - 6 Mi to Downtown Milwaukee!
House (4 Bedrooms) | Interior

Pet-friendly Home - 6 Mi to Downtown Milwaukee!

3.0 star property
Pet-friendly Home - 6 Mi to Downtown Milwaukee!
Riverfront Retreat ~ 4 Mi to Downtown Milwaukee!
Microwave, oven, stovetop, dishwasher

Riverfront Retreat ~ 4 Mi to Downtown Milwaukee!

3.0 star property
Riverfront Retreat ~ 4 Mi to Downtown Milwaukee!
Cozy Milwaukee Home: 3 Mi to Whitefish Bay!
House (3 Bedrooms) | Private kitchen

Cozy Milwaukee Home: 3 Mi to Whitefish Bay!

3.0 star property
Cozy Milwaukee Home: 3 Mi to Whitefish Bay!
Comfortable Milwaukee Abode ~ 10 Mi to Downtown!
House (3 Bedrooms) | Private kitchen

Comfortable Milwaukee Abode ~ 10 Mi to Downtown!

3.0 star property
Comfortable Milwaukee Abode ~ 10 Mi to Downtown!
6 Mi to Summerfest Park: Home w/ Game Room!
Interior

6 Mi to Summerfest Park: Home w/ Game Room!

3.0 star property
6 Mi to Summerfest Park: Home w/ Game Room!
Boho Art cottage in hip Bay View, Milw neighborhood- 3bed, Sauna, Hot Tub
Property grounds

Boho Art cottage in hip Bay View, Milw neighborhood- 3bed, Sauna, Hot Tub

Boho Art cottage in hip Bay View, Milw neighborhood- 3bed, Sauna, Hot Tub
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.
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

Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

10/10 Excellent
"Really nice hotel all around for business or pleasure visit to Milwaukee. Great location, great service, nice rooms and amenities, and great breakfast!"
Robert 1-night trip
Posted 1 day ago
Drury Plaza Hotel Milwaukee Downtown

Frequently asked questions

What is there to do in Greendale near my cottage?
Greendale has enough experiences and activities to entertain you for weeks (or months!), beginning with Harley-Davidson Museum. Milwaukee County Zoo, Milwaukee Art Museum and Riverside Theatre are other awesome attractions. If you're lingering longer, Pabst Theatre and Discovery World are nice final touches to your itinerary.