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Our top choices for Greendale holiday homes

A living room with a leather sofa, a round coffee table, and a dining area with a table and chairs.

A bedroom with a wooden bed frame, a white quilted bedspread, two gray pillows, a wooden dresser with a mirror, and a lamp.

A kitchen with wooden cabinets, a granite countertop, a sink, and a dining area with a bench and table.

A covered patio area with outdoor furniture, a small table, and a potted plant.

1. 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, (55 reviews)

9.8/10

Exceptional

(55 reviews)

"Stayed here many times. Great as always."

Kristi T.

The price is HK$1,391

HK$1,391

HK$2,677 total

includes taxes & fees

26 Sept - 27 Sept

Historic home - walk to village center. Original features with modern updates.

A dining area with a ceiling fan, wooden dining table, chairs, and a view of the outdoors through large windows.

A deck with outdoor furniture, a fire pit, and a view of a house.

A yellow single-story building with a brick facade, a red door, and a small front yard.

A bedroom with a bed, nightstand, dresser, chair, window, and a ceiling fan.

2. New Spacious 8-bedroom house on large private lot close to Milwaukee attractions

New Spacious 8-bedroom house on large private lot close to Milwaukee attractions

Milwaukee

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"This property was perfect for our needs!"

Amanda D.

The price is HK$1,342

HK$1,342

HK$4,190 total

includes taxes & fees

23 Sept - 24 Sept

New Spacious 8-bedroom house on large private lot close to Milwaukee attractions

A metal-framed table with a wooden top, mesh storage compartments, and a vase with flowers.

A kitchen with a microwave, coffee maker, and pantry sign.

A neatly made bed with a white and blue duvet, a dark headboard, and a bedside lamp.

3. Quiet Bay View Getaway

Quiet Bay View Getaway

Town of Lake

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

"Having to navigate the stairs to the basement at our age was a little difficult and could use a kitchen sink but other than that it was fine."

Carl B.

The price is HK$949

HK$949

HK$1,785 total

includes taxes & fees

24 Sept - 25 Sept

Quiet Bay View Getaway

A modern kitchen with light wood cabinets, a stainless steel refrigerator, a stove, and a marble countertop.

A two-story house with a front porch, a wooden staircase, and a small front yard.

A modern living room with a fireplace, a sofa set, a coffee table, and a TV mounted on the wall.

A modern living room with a grey sofa, a round coffee table, and a lamp.

4. 3-bedroom bungalow with WiFi vibrant Milwaukee

3-bedroom bungalow with WiFi vibrant Milwaukee

Milwaukee

9.6 out of 10, Exceptional, (14 reviews)

9.6/10

Exceptional

(14 reviews)

"Beautiful property! We had a great stay!"

VJ P.

The price is HK$1,287

HK$1,287

HK$3,432 total

includes taxes & fees

23 Sept - 24 Sept

3-bedroom bungalow with WiFi vibrant Milwaukee

An outdoor patio with a table and chairs, string lights, a wooden fence, and a tree.

A living room with a fireplace, a television mounted above it, and a dining area visible through an open doorway.

A living room with a sofa, coffee table, and a desk with a chair. There are windows with curtains, a hanging light fixture, and a wall-mounted plant.

5. Mins to State Fair & AmFam Field |Sleeps 12|4BR + Parking

Mins to State Fair & AmFam Field |Sleeps 12|4BR + Parking

Bluemound Heights

9.0 out of 10, Wonderful, (4 reviews)

9.0/10

Wonderful

(4 reviews)

"Great place to stay!"

Suzanne S.

The price is HK$1,510

HK$1,510

HK$4,624 total

includes taxes & fees

23 Sept - 24 Sept

Mins to State Fair & AmFam Field |Sleeps 12|4BR + Parking

A living room with a ceiling fan, a sofa, a coffee table, and a dining area with a table and chairs.

A wooden deck with outdoor furniture, including chairs and a table.

A two-story brick house with a sloped roof, a covered porch, and a well-maintained lawn.

A corner room with two wooden chairs, a small table, a stained glass window, and a patterned rug.

6. Charming Bungalow / Heart of Bay View / Parking - Central Air - Deck

Charming Bungalow / Heart of Bay View / Parking - Central Air - Deck

Bay View

10.0 out of 10, Exceptional, (38 reviews)

10/10

Exceptional

(38 reviews)

"Great place to stay in Milwaukee! The house was clean and very well stocked with everything we could need! I didn’t realize someone lived upstairs, but there wasn’t any issues with it. The neighborhood was close to many great things to do We would definitely stay here again!"

Jenna H.

The price is HK$1,412

HK$1,412

HK$3,487 total

includes taxes & fees

6 Oct - 7 Oct

Charming Bungalow / Heart of Bay View / Parking - Central Air - Deck

A bed with a wooden headboard, a green pillow, and a tray with food and a glass of orange juice.

A dining area with a table set for four, chairs, a bookshelf with board games, and a living room in the background.

A kitchen with wooden cabinets, a stainless steel refrigerator, a dining area with a table and chairs, and a hanging light fixture.

A dining area with a wooden table set for six, a chandelier, and a view of the backyard through large windows.

7. Game Night Haven with Gas Fireplace

Game Night Haven with Gas Fireplace

Oak Creek

The price is HK$3,226

HK$3,226

HK$4,338 total

includes taxes & fees

23 Sept - 24 Sept

Game Night Haven with Gas Fireplace

Outdoor seating with wicker chairs and red umbrellas, a 'DO NOT ENTER' sign, and a building with 'noodles & company' signage.

A dining area with a round table, wooden chairs, a chandelier, and a window seat with cushions.

A kitchen with white cabinets, a microwave, a coffee maker, and a window.

A living room with a fireplace, two patterned armchairs, a dining table with chairs, and a chandelier.

8. House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

Johnson Woods

9.6 out of 10, Exceptional, (47 reviews)

9.6/10

Exceptional

(47 reviews)

"Nice quite spot close to highway"

Dan K.

The price is HK$1,451

HK$1,451

HK$2,867 total

includes taxes & fees

29 Sept - 30 Sept

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

A dining area with a long table, pink chairs, and a chandelier.

A pink-themed living room with two sofas, a coffee table, and a Christmas tree.

A pink-themed room with a clear glass coffee table, a pink sofa, and a pink rug.

A kitchen with pink cabinets, a stainless steel refrigerator, a marble countertop, and a chandelier.

9. Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

Bay View

9.8 out of 10, Exceptional, (28 reviews)

9.8/10

Exceptional

(28 reviews)

"Great place!"

Kathy R.

The price is HK$1,967

HK$1,967

HK$3,485 total

includes taxes & fees

1 Oct - 2 Oct

Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

A bar area with a counter, four bar stools, and a framed picture above the counter.

A kitchen with white cabinets, a stainless steel dishwasher, and a granite countertop.

A kitchen with a built-in shelf unit containing kitchenware, a coffee maker, and a framed American flag.

A bedroom with a bed, a window with blinds, a wardrobe, a mirror, and a rug.

10. King Bed • Vintage Urban Oasis • Near MKE Airport

King Bed • Vintage Urban Oasis • Near MKE Airport

Town of Lake

The price is HK$1,093

HK$1,093

HK$2,177 total

includes taxes & fees

28 Sept - 29 Sept

King Bed • Vintage Urban Oasis • Near MKE Airport

A bedroom with a large bed, two side tables, a lamp, and a view of trees through the windows.

A two-story house with a front porch, a stone foundation, and a large tree in front.

A modern living room with a sectional sofa, a round coffee table, and a chandelier.

A kitchen with a stainless steel stove, oven, and a kettle. There is a wooden shelf with glasses and a metal rack with mugs.

11. Spacious House Near American Family Field+State Fair

Spacious House Near American Family Field+State Fair

West Allis

The price is HK$1,836

HK$1,836

HK$3,843 total

includes taxes & fees

4 Oct - 5 Oct

Spacious House Near American Family Field+State Fair

A dining table with a bottle of wine, glasses, and a potted plant.

A modern living room with a sofa, a coffee table, and a TV. There is a kitchen area with a refrigerator, microwave, and bar stools.

A building with a sloped roof, large windows, and a garage door.

A dining area with a wooden table, chairs, a hanging light fixture, a potted plant, and a wall-mounted map.

12. Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms

Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms

Bay View

10.0 out of 10, Exceptional, (20 reviews)

10/10

Exceptional

(20 reviews)

"Best stay"

Marvin G.

The price is HK$1,765

HK$1,765

HK$4,172 total

includes taxes & fees

30 Sept - 1 Oct

Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms

A living room with a blue sofa, a yellow armchair, a coffee table, and a large window.

A single-story house with a front garage, a small porch, and a chimney.

A modern kitchen with white cabinets, a stainless steel refrigerator, blue cabinets, a wooden dining table, and a black stove.

A bedroom with a bed, a window, and wooden flooring.

13. Charming 2-bedroom house with everything you need in the heart of West Allis

Charming 2-bedroom house with everything you need in the heart of West Allis

West Allis

9.6 out of 10, Exceptional, (18 reviews)

9.6/10

Exceptional

(18 reviews)

"Had a great weekend stay. House was clean and cute and our host was very accommodating!"

Renee W.

The price is HK$1,059

HK$1,059

HK$2,229 total

includes taxes & fees

22 Oct - 23 Oct

Charming 2-bedroom house with everything you need in the heart of West Allis

A two-story house with a stone facade and a white exterior.

A living room with a fireplace, a wooden door, and a window with curtains.

A dining area with a wooden table and chairs, a chandelier, and a staircase with wooden railings.

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a large island with a sink.

14. Cozy home by the lake

Cozy home by the lake

Cudahy

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"We had a great stay. Places to eat close by. We walked to a great Italian restaurant. Our hosts communication was above and beyond. Even though it is a duplex type house, it is very quiet. No noise issues at any time. Plenty of parking and nice backyard."

Jilda L.

The price is HK$2,354

HK$2,354

HK$5,192 total

includes taxes & fees

10 Oct - 11 Oct

Cozy home by the lake

A fire pit surrounded by wooden Adirondack chairs on a paved patio, with string lights and a wooden fence in a wooded backyard.

A living room with a sofa, a coffee table, a bench, and a fireplace.

A modern fireplace with a glass front, a wooden shelf above it with lit candles, and a framed abstract painting on the wall.

A modern two-story house with a stone facade, large windows, and a well-maintained lawn.

15. The Eucalyptus — A 4 bedroom Retreat

The Eucalyptus — A 4 bedroom Retreat

Cannon Park

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Great location, very clean."

James M.

The price is HK$1,236

HK$1,236

HK$3,611 total

includes taxes & fees

14 Oct - 15 Oct

The Eucalyptus — A 4 bedroom Retreat

A cozy outdoor seating area with wicker furniture and a glass table, set against a stone wall and under string lights.

A modern kitchen with a stainless steel stove, oven, and dishwasher. There is a window with a view of trees, a ceiling fan, and a wooden backsplash.

A dining area with a wooden table and chairs, a decorative partition with plants, and a kitchen area in the background.

A living room with a brown leather sofa, a glass table with a tray holding a green drink, a remote control, and a decorative vase with lights.

16. Quincy Estate 5BR/3BA for Family Stays with Fireplace Park Views & Parking

Quincy Estate 5BR/3BA for Family Stays with Fireplace Park Views & Parking

Bay View

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

" Easy check in, well stocked and perfect location. "

robin h.

The price is HK$3,354

HK$3,354

HK$5,564 total

includes taxes & fees

23 Sept - 24 Sept

Quincy Estate 5BR/3BA for Family Stays with Fireplace Park Views & Parking

A spacious living room with a large TV, a wooden coffee table, and a gray sofa. There is a dining area with a table and chairs, and a kitchen area with a fridge and a microwave.

A spacious living room with a sofa set, a coffee table, and a bookshelf.

A modern kitchen with a central island, pendant lighting, and a view to the outside.

A patio with a red umbrella, outdoor furniture, and potted plants.

17. Barclay House in Walker's Point

Barclay House in Walker's Point

Fifth Ward

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"Very nice and comfortable home."

Tom L.

The price is HK$1,624

HK$1,624

HK$2,941 total

includes taxes & fees

23 Sept - 24 Sept

Barclay House in Walker's Point

A spacious hallway with wooden flooring, a central dining table with chairs, a chandelier, and a bookshelf with books.

A cozy living room with a leather sofa, a bookshelf, a fireplace, and wooden doors.

A wooden deck with potted plants, a fire pit, and outdoor furniture.

A spacious living room with a large leather sofa, a smaller sofa, a coffee table, and a fireplace.

18. Three Bedroom Upper

Three Bedroom Upper

Riverwest

9.6 out of 10, Exceptional, (102 reviews)

9.6/10

Exceptional

(102 reviews)

"Great stay comfortable place I would most definitely come back "

Crystiana H.

The price is HK$1,306

HK$1,306

HK$1,725 total

includes taxes & fees

23 Sept - 24 Sept

Three Bedroom Upper

A spacious living room with a spiral staircase, wooden flooring, a large potted plant, and a modern air conditioning unit.

A spacious living area with a wooden staircase, a bench with cushions, a large mirror, and a rustic rug.

A bedroom with a large bed, a dresser, a ceiling fan, and skylights.

A room with a wooden floor, a desk with a chair, a potted plant, and a large wooden cabinet.

19. Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions

Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions

Lower East Side

9.6 out of 10, Exceptional, (41 reviews)

9.6/10

Exceptional

(41 reviews)

"Nice location"

Lyndsay K.

Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions

A modern kitchen with dark cabinets, a white island, blue bar stools, and a window with a view.

A billiards table in a room with a green carpet, a grey sofa, and a television mounted on the wall.

A kitchen with a large island, pendant lights, a refrigerator, and a window.

A residential property with a pathway leading to a house, surrounded by greenery and a wooden fence.

20. 6 Mi to Summerfest Park: Home w/ Game Room!

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

Cudahy

8.8 out of 10, Excellent, (8 reviews)

8.8/10

Excellent

(8 reviews)

"Excellent house. Great location. Thanks for the pleasant stay. "

Joe K.

The price is HK$1,036

HK$1,036

HK$4,010 total

includes taxes & fees

4 Oct - 5 Oct

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

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

The Pfister Hotel

10/10 Excellent

"Enjoyed our stay. Confidently located to activities."

Michael 1-night trip

Posted 1 hour ago

The Pfister Hotel

The Marc Hotel

10/10 Excellent

"Excellent room, it was a suite! Connected to Hilton. Starbucks and great restaurant options. Safe. Connected to Baird Center conference venue and downtown shops."

Kim 3-night trip

Posted 3 hours ago

The Marc Hotel