Holiday houses in Waukesha

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Top-rated holiday rentals in Waukesha

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Guest favourite
Home in Waukesha
4.93 out of 5 average rating, 190 reviews

Pet-Friendly Retreat•Sleeps 8•Huge Yard•Fire pit

Wake up to sunrise over a peaceful backyard and enjoy your morning coffee on the private balcony. Evenings are perfect by the fire pit under a starry sky. Just a 5 minute drive from Pewaukee Lake Pet-friendly home with a large yard and fire pit - ideal for relaxing and spending time together. Open-concept living, kitchen, and dining area creates a warm, inviting space to gather. Sleeps up to 8 and is best suited for small families or close-knit groups who prefer a more cozy, intimate layout.

Top Guest favourite
Guesthouse in Delafield
5 out of 5 average rating, 15 reviews

Private Guest Apt - .4 miles to Downtown Delafield

Welcome to your peaceful retreat in Delafield! This new-construction, 600 sq ft private apartment offers a perfect balance of comfort, privacy, and convenience. Although attached to our single-family home, the apartment is completely separate with its own private entrance, dedicated parking spot, & quiet setting just steps from the lake. Located within walking distance to downtown Delafield, you’re close to fantastic restaurants, boutique shops, coffee spots, and scenic walking & biking paths.

Top Guest favourite
A historic home features a multi-gabled roof and intricate architectural details. The exterior showcases a blend of light and dark hues, complemented by well-maintained landscaping and a spacious lawn. A charming porch wraps around the front, providing an inviting entrance with rocking chairs nestled on one side.
Home in Wales
4.95 out of 5 average rating, 200 reviews

Beautifully Restored Historic Victorian

Whether this is for a single, couple, or small group, your stay at this historic home will truly be memorable. You’ll love the MBR suite featuring a gas fireplace, whirlpool tub, and double walk-in custom tile shower. There is an additional very nice full bath/shower on the main floor. The finished lower level has two separate rooms, each with a quality double futon with bedding available for your guests. For this attractive price, the upper 4 bedrooms are locked but may be opened for more

Top Guest favourite
A paved driveway winds through a lush wooded area, bordered by greenery and tall trees. The home can be seen nestled in the distance, blending harmoniously with the natural surroundings.
Home in Muskego
4.89 out of 5 average rating, 141 reviews

Muskego Hideaway on 2 Acre Lot

Forget your worries in this beautifully updated 4 bedroom, 2 bath home on a 2 acre wooded hillside. Convenient location with easy access to the Milwaukee airport. Only a minute's drive to Little Muskego Lake and the sandy beach at Idle Isle Park. Easy drives to Alpine Valley, Lake Geneva, and The Rock Sports Complex. Only 2 minutes from I43 for easy access to Milwaukee for Brewers, Bucks, and the many festivals. Relax on the deck or patio and watch the deer and other wildlife in the backyard.

Top Guest favourite
Guest suite in Waukesha
4.97 out of 5 average rating, 71 reviews

Tucked Away

For those in need of a "home away from home" while on the road working or just passing though on your travels. This private, quaint backyard parking/entrance mini apartment located in Waukesha's "Historic District" is for you. Enjoy large outer deck as weather permits. Stairs are required outside to enter unit. Walking distance to downtown area. Easy access from this location to Madison (65 miles) and Milwaukee (12 miles). Located near Carroll University and Waukesha Memorial Hospital.

Guest favourite
A dining area features a round table surrounded by black chairs with plush white cushions. Sunlight filters through large windows, highlighting the vintage sideboard and plant. An inviting living space is visible through an archway, showcasing a blend of decor and natural light.
Bungalow in West Milwaukee
4.97 out of 5 average rating, 195 reviews

Adorn Abode

Charming upper level hygge bungalow (2 unit home total). Ten minutes from anywhere. Tucked away in the quiet village of West Milwaukee. Full of natural light and curated vintage decor. Walking distance to a few restaurants and bars, as well as the American Family Field. Enjoy a cocktail on the front balcony and watch the sunset while indulging in a classic vinyl collection. Small balcony off of the kitchen to watch the sunrise and enjoy a cup of coffee. Perfect for adventuring or relaxing.

Top Guest favourite
A cozy sleeping area features a wrought iron bed with white linens and several pillows. Two nightstands with lamps are placed on either side. A fan is mounted on the ceiling, while emerald green curtains frame a window beside a floral wall art piece.
Apartment in West Allis
4.97 out of 5 average rating, 118 reviews

Nice 1 BR Apt, WIFI & Office, Near State Fair

This beautifully furnished upper duplex offers a cozy and comfortable living space in a safe and peaceful neighborhood. The kitchen comes fully equipped with all the necessary supplies for cooking and dining, and the garage and driveway provide convenient parking options. Stay connected with the included WIFI and watch YouTube TV. Nice Office space. Conveniently located near major freeways, downtown, hospitals, and the State Fair Grounds. Book now for a stress-free and enjoyable stay

Top Guest favourite
A historic stone home is presented, featuring multiple windows that enhance its classic appeal. A well-maintained garden with colorful flowers surrounds the exterior, creating a welcoming entrance to the Butler Place. A sign displaying the property's name is held by two guests in front of the house.
Guest suite in Sussex
4.96 out of 5 average rating, 331 reviews

The Loft @ The Butler Place. 1846 homestead.

The Loft at the Butler Place is a beautiful, quiet retreat set in the rural suburb of Sussex, just 30 minutes west of Milwaukee. The home is the 1846 homestead of the William Butler family, making the home older than the State of Wisconsin! The 2019 remodel of the Loft is in sophisticated farmhouse style and pays tribute to the history of the home in its furnishings, up cycled pieces, and beautiful setting. "Broken becomes blessed" both tells and compells as an invitation to all.

Superhost
A cozy living area features a spacious sofa against a vibrant, textured wall. A colorful area rug adds warmth to the hardwood floor, while framed artwork decorates the surrounding walls. Access to the kitchen and stairway is visible in the background.
Home in McCarty Park
4.82 out of 5 average rating, 188 reviews

Designer Cottage-Parking, Patio, & New Kitchen

LOCATION, LOCATION! • Fast Fiber Internet TIME (MIN) 5-10 McCarty Park (Water Park, Trails, B-Ball Court) STATE FAIR TOSA 10-15 Brewers, Bucks Harley, 3rd Ward Breweries, Zoo ATTN MEDICAL Near All Hospitals PRIVATE PATIO & FENCED-BACKYARD • Seating for 4 w/ table • 🐶 can roam • Safe & secure kids play • Space for games & bags SAFE PARKING • Allows 2-4 vehicles inc. trucks & boats • 100FT off street • driveway widens LAUNDRY • W&D • Pods & D-Sheets • Util. Sink • Iron+Board

Top Guest favourite
Tall sunflowers bloom vibrantly in a garden, displaying bright yellow and orange petals. A wooden gazebo with hanging lights stands in the background, surrounded by lush greenery. Soft sunlight filters through the trees, enhancing the serene outdoor setting.
Guest suite in Sussex
4.99 out of 5 average rating, 150 reviews

Garden Retreat in law Suite

Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

Top Guest favourite
A welcoming living area features a dark leather sofa and loveseat, complemented by a wood coffee table atop a plush area rug. Natural light enters through two windows, enhancing the space's warmth. Artwork is displayed on the wall, adding a touch of character.
Apartment in West Allis
4.96 out of 5 average rating, 216 reviews

Clean 2 bedroom/1 bath close to everything!

Charming, recently and tastefully furnished 2 bedroom 1 bathroom apartment with private entrance and parking. Close to downtown, shopping malls, zoo, hospital, airport, and main freeways. Full kitchen with stove, microwave, coffee pot, toaster, and kitchenware. Unit has TVs and WiFi. Coin operated laundry is accessible in building. Why stay at a hotel when you can feel at home in this lovely unit?

Guest favourite
A charming two-story family home is seen through vibrant autumn foliage, showcasing yellow and orange leaves. A white wooden fence borders the property, with fallen leaves scattered across the lawn. The house features an upper balcony and large windows welcoming natural light.
Home in Oconomowoc
4.82 out of 5 average rating, 171 reviews

Quiet Lake Country Retreat

Charming single family home located in the Village of Oconomowoc Lake. Well appointed for longs stays or perfect for a weekend retreat. Easy access to I94 and Hwy. 16. Minutes away from Olympia Resort, stores, restaurants, downtown Oconomowoc. 10 minute drive to Delafield. 20 minute drive to Erin Hills, site of the 2017 US Open. 35 minutes to downtown Milwaukee. 45 minutes to Madison.

Popular amenities for Waukesha holiday rentals

When is the best time to visit Waukesha?

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Frequently Asked Questions

  • How much does it cost to stay in house rentals in Waukesha?

    Experience the best of Waukesha with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Waukesha?

    Yes! Work meets play with ease at over 30 vacation rentals in Waukesha featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Waukesha?

    Make yourself at home in Waukesha by choosing from our most frequently booked neighborhoods. We have over 30 vacation rentals in Meadowbrook Heights, over 60 vacation rentals in Thielemans Heights, and over 10 vacation rentals in Springbrook.

  • Are there family-friendly vacation rentals in Waukesha?

    Waukesha has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Waukesha?

    Four-legged friends are welcome in Waukesha. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Do house rentals in Waukesha have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Waukesha. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Waukesha have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Waukesha. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Waukesha?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Waukesha

  • Total holiday rentals

    Explore 50 holiday rentals in Waukesha

  • Nightly prices starting at

    Waukesha holiday rentals start at $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,600 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Waukesha holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Waukesha rentals

  • 4.7 Average rating

    Waukesha stays receive an average rating of 4.7 out of 5 from guests

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