Milwaukee Holiday Homes from £119: Search Holiday Homes in Milwaukee

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Our top choices for Milwaukee holiday homes

A beach with people walking and swimming, a lifeguard tower, and a clear sky.

1. 2bed 1.5bath House, Lower Eastside, King Bed, Fire Pit, Sleeps 6

Downtown Milwaukee

Kristen M.

includes taxes & fees

9 Nov - 10 Nov

A dining area with a round table, four chairs, a wooden floor, a door, and a lamp.

2. Quiet House

Milwaukee

Steven

includes taxes & fees

30 Nov - 1 Dec

A modern living room with a large flat-screen TV, a round coffee table, a sofa, and a view of a cityscape through large windows.

3. Serene 3-Bedroom Milwaukee Retreat Basketball Court & Fitness Room

Westown

Irvin J.

includes taxes & fees

30 Nov - 1 Dec

A modern kitchen with white cabinets, a stainless steel stove, and a wooden countertop.

4. Remodeled Home - Steps from Brady Street!

Downtown Milwaukee

Kevin M.

includes taxes & fees

9 Nov - 10 Nov

5. The Bentley - Frida's Reign, Heart of Walkers Point w/Garage,Yard

Fifth Ward

Holly B.

includes taxes & fees

8 Nov - 9 Nov

6. The Pink Lady - Stylish Walker’s Point Home

Fifth Ward

syed a.

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with a white refrigerator, wooden cabinets, and a built-in oven.

7. Workspace • Coffee Bar • Modern 4BR • Sleeps 10

Milwaukee

includes taxes & fees

9 Nov - 10 Nov

A room with a wooden floor, a television on a stand, a white door, and a window with a view of buildings outside.

8. Best location in Milwaukee! Upper Duplex Unit

Downtown Milwaukee

Aaron W.

includes taxes & fees

9 Nov - 10 Nov

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.

9. Barclay House in Walker's Point

Fifth Ward

Brianna E.

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

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

Johnson Woods

Dan K.

includes taxes & fees

18 Nov - 19 Nov

A dining area with a table set for two, a coffee maker, and a window with blinds.

11. 1BR Pro Flat + Office; near Hospitals. Garage + Yard

Fair Park

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

12. Three Bedroom Upper

Riverwest

Michelle J.

includes taxes & fees

9 Nov - 10 Nov

A neatly made bed with white bedding, a vase with flowers, a tray with a cup and saucer, and a magazine on the bed.

13. Workspace • Fireplace • Coffee Bar • Sleeps 12

Milwaukee

Chris B.

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a sloped ceiling, a bed with a red blanket, a bedside lamp, and a large mirror.

14. Modern Milwaukee Getaway

Lower East Side

Karson

includes taxes & fees

9 Nov - 10 Nov

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

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

Bay View

Pamela M.

includes taxes & fees

18 Nov - 19 Nov

A living room with a large brown sofa, a dining area with wooden chairs, and a kitchen area with a refrigerator and microwave.

16. Be Relax House, Cozy 2BR Milwaukee Getaway, Sleeps 4

Milwaukee

includes taxes & fees

16 Nov - 17 Nov

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

17. Quiet Bay View Getaway

Town of Lake

Carl B.

includes taxes & fees

30 Nov - 1 Dec

A Victorian-style house with a prominent front staircase, multiple windows, and lush greenery.

18. Classic Victorian with modern amenities in the heart of Downtown Milwaukee

Downtown Milwaukee

Andrew H.

includes taxes & fees

9 Nov - 10 Nov

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

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

Lower East Side

Andrew C.

includes taxes & fees

8 Nov - 9 Nov

A living room with a flat-screen TV, two sofas, a coffee table, and a large window with wooden frames.

20. Sunny & Spacious 4BR East Side Stay ¦ Balcony ¦ Family-Friendly

Upper East Side

Mike G.

includes taxes & fees

18 Nov - 19 Nov

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Milwaukee and related destinations

Explore the Milwaukee Art Museum's wing-like architecture that opens and closes daily over Lake Michigan's shoreline. Brewery tours, summer festivals, and the Harley-Davidson Museum offer perfect ways to experience the city's blend of industrial heritage and lakefront charm.

See all hotels in Milwaukee

A city skyline with modern skyscrapers and a river in the foreground.

Top reviews in Milwaukee

A multi-story hotel with a prominent sign at the top.

Drury Plaza Hotel Milwaukee Downtown

Downtown Milwaukee

10/10 Excellent

Christopher

A grand lobby with ornate columns, a chandelier, and a staircase leading to an upper level.

The Pfister Hotel

Downtown Milwaukee

10/10 Excellent

Nicholas

An outdoor seating area with round tables and chairs, covered by umbrellas, and surrounded by red flowers.

County Clare Irish Hotel & Pub

Downtown Milwaukee

10/10 Excellent

Anonymous traveller

A modern outdoor seating area with a fire feature, overlooking a cityscape with tall buildings and a view of the street.

The Trade, Autograph Collection

Westown

10/10 Excellent

Sukhdeep

An outdoor seating area with tables and chairs, a fire pit, and a covered section with a bench and a sofa.

Home2 Suites By Hilton Milwaukee West

West Allis

10/10 Excellent

John

An outdoor seating area with tables, chairs, and a fire feature.

Hyatt Place Milwaukee/Downtown

Westown

10/10 Excellent

Anne

A building with a 'Inn' sign, large arched windows, and a well-lit entrance.

Kinn Guesthouse Downtown

Downtown Milwaukee

8/10 Good

This property is beautifully styled. My suite was over 35m2 and on a corner. The furnishings are stylish and well curated. The bed was massive and very soft, too soft for me but a great bed none the less. Outside the room is a common area with a stunning high end kitchen with dare cooking and food storage areas. Free nespresso and Rishi tea, free pastries and yogurt and granola. Utterly gorgeous. The hotel works entirely with out a front desk and no keys. Access is all via a key code sent to...

Mark