
Holiday houses in Milwaukee
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Top-rated holiday rentals in Milwaukee
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Milwaukee holiday rentals
Other great holiday rentals in Milwaukee
Guest favourite

Private room in Greenfield
4.91 out of 5 average rating, 331 reviewsSpacious Downstairs Suite/private bathroom
Top Guest favourite

Private room in Riverwest
5 out of 5 average rating, 27 reviewsLuxury private room with balcony!
Superhost

Private room in Riverwest
4.86 out of 5 average rating, 69 reviewsThe Native.
Top Guest favourite

Private room in Milwaukee
5 out of 5 average rating, 41 reviewsArtsy Digs, private room in home hosted by Johanna

Private room in Milwaukee
5 out of 5 average rating, 3 reviewsCozy & Modern Retreat
Top Guest favourite

Private room in Milwaukee
4.98 out of 5 average rating, 61 reviewsLannon Stone Beauty
Top Guest favourite

Private room in Brookfield
5 out of 5 average rating, 79 reviewsFrank Lloyd Wright: Spring Green Room

Hotel room in Brookfield
4.67 out of 5 average rating, 202 reviewsFamily Retreat | Museums . Free Shuttle
Quick stats about holiday rentals in Milwaukee
Total rentals
2.5K properties
Total number of reviews
107K reviews
Family-friendly rentals
1.5K properties are a good fit for families
Pet-friendly rentals
780 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
1.4K properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Holiday rentals
- Lake Geneva Holiday rentals
- Madison Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Haven Holiday rentals
- Holland Holiday rentals
- Saugatuck Holiday rentals
- South Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Chicago Holiday rentals
- Rentals with a hot tub Milwaukee
- Waterfront rentals Milwaukee
- Rentals with a patio Milwaukee
- Condo rentals Milwaukee
- Rentals with outdoor seating Milwaukee
- Rentals with an EV charger Milwaukee
- Rentals with a fire pit Milwaukee
- Rentals with a washing machine and dryer Milwaukee
- Rentals with a fireplace Milwaukee
- Apartment rentals Milwaukee
- Kid-friendly rentals Milwaukee
- Pet-friendly rentals Milwaukee
- Rentals with beach access Milwaukee
- Smoking-friendly rentals Milwaukee
- Rentals with pools Milwaukee
- Loft rentals Milwaukee
- Rentals with lake access Milwaukee
- Fitness-friendly rentals Milwaukee
- Rentals with breakfast Milwaukee
- Mansion rentals Milwaukee
- Lakehouse rentals Milwaukee
- House rentals Milwaukee
- Yurt Rentals United States
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- Houseboats United States
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- Holiday Chalets United Kingdom
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- Mansion Rentals United States
- Villa Rentals United Kingdom
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- Holiday Apartments Australia
- Holiday Houses United States
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- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
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- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
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- Beach Houses United Kingdom
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- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Six Flags Great America
- Erin Hills Golf Course
- Alpine Valley Resort
- Kohler-Andrae State Park
- Milwaukee Public Museum
- Geneva National Resort & Club
- Illinois Beach State Park
- Harrington Beach State Park
- Bradford Beach
- Grand Geneva Resort & Spa
- Racine North Beach
- Milwaukee County Zoo
- Richard Bong State Recreation Area
- Wilmot Mountain Ski Resort
- Discovery World
- The Bull at Pinehurst Farms Golf Course
- Milwaukee Country Club
- West Bend Country Club
- Heiliger Huegel Ski Club
- Springs Water Park
- The Mountain Top Ski & Adventure Center at Grand Geneva
- America's Action Territory
- Sunburst
- Blue Mound Golf and Country Club