Holiday houses in Waukesha

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Top-rated holiday rentals in Waukesha

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Home in Waukesha
4.93 out of 5 average rating, 197 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
The modern farmhouse is viewed from a distance, showcasing its clean white exterior and well-maintained landscaping. A paved driveway leads to the entrance, flanked by neatly trimmed bushes and vibrant green grass, creating an inviting approach to the home.
Home in Delafield
4.99 out of 5 average rating, 161 reviews

Modern Lake Country Farmhouse in Delafield

Just a half mile outside downtown Delafield, this charming, modern farmhouse is clean, updated and well stocked. There's plenty of space to have a peaceful, relaxing stay. Easy access to golf, lakes (like Nagawicka and Upper & Lower Nemahbin), parks (like Lapham Peak State Park), hiking, biking and x-country skiing. Enjoy walking access to restaurants and shops in Delafield. Just minutes off I-94 in Lake Country, conveniently located between Milwaukee and Madison. 30 minutes from Fiserv Forum.

Guest favourite
The exterior of a charming house is showcased, featuring a welcoming front porch adorned with string lights. Lush greenery surrounds the home, with a flower garden displaying purple blooms. A pathway leads to the entrance, enhancing the inviting atmosphere of the property.
Home in Menomonee Falls
4.93 out of 5 average rating, 201 reviews

Exhale, rest

Exhale. The perfect combination. This home is right in the village of Menomonee Falls with great shopping and restaurants within walking distance. Close to the highway, it’s also a mere half an hour to anything Milwaukee so games, museums, festivals are all also at your fingertips. At the end of dead end road with views of the river, access to trails, and a secluded deck and fire pit, there is definitely also a rural feel. This location has it all. Go out, live life, come back, exhale and rest.

Top Guest favourite
A two-story home is surrounded by vibrant autumn foliage, featuring large trees displaying rich yellow and orange leaves. A gravel driveway leads up to the house, with fallen leaves carpeting the ground. A garage is visible in the background, adding to the serene neighborhood setting.
Guest suite in Brookfield
5 out of 5 average rating, 272 reviews

In the Canopy (beautiful Brookfield/Milwaukee)

Relax “in the Canopy” of beautiful maples! If you’re looking for party central…this isn’t it. But if you want a comfortable place in a tree-filled neighborhood, just a few minutes from all the best Milwaukee has to offer, you’re in luck! Perfect location for quick access to the city—or to Lake Country to the west. Quiet, comfortable, safe, surrounded by beautiful gardens. We’re in a perfect launching spot to visit Summerfest, Brewers/Bucks games, or Milwaukee's western suburbs. Bring the kids!

Top Guest favourite
An A-frame structure is nestled among lush green trees, showcasing large glass windows that allow for ample natural light. The contrasting wood siding complements the surrounding foliage, creating a harmonious blend with nature. A raised deck leads to the entrance, enhancing accessibility to the home.
Cabin in Fontana-on-Geneva Lake
4.93 out of 5 average rating, 182 reviews

Exquisite Modern A-frame all WithInnReach

An amazing space that truly caters to the guest experience. We've built this art piece to have our guests immerse themselves in all the amenities, from heated floors to in-ceiling speakers - all whilst losing yourself in the wood burning fireplace. At WithInnReach the attention to detail was paramount - with an emphasis of what we enjoy...amazing food through a well balanced kitchen, beautiful sound through Klipsch speakers and relaxation with floor to ceiling showers...enjoy to the fullest.

Guest favourite
A spacious living area features a blue sectional sofa and a yellow accent chair, offering an inviting seating arrangement. A brown coffee table sits on a patterned rug, while large windows allow for natural light. A desk with a chair is positioned nearby for work or leisure.
Home in West Allis
4.87 out of 5 average rating, 123 reviews

West Allis Oasis

Welcome to our cozy 2-bedroom, 1-bathroom home on a quiet street in a fantastic neighborhood. Dog-friendly and perfect for families or solo travelers, enjoy easy access to I-94 and the State Fair Park just a few blocks away. Our home offers a peaceful retreat with comfortable furnishings, a fully equipped kitchen, cozy bedrooms, and large fenced in yard. Relax and unwind in a tranquil environment after a day of exploring. Book your stay today for the perfect blend of comfort and convenience!

Top Guest favourite
A spacious outdoor deck is featured, overlooking a lush green backyard. Visible are various plants and garden elements, along with a patio umbrella. Stairs lead down from the deck to the garden area, providing access to the vibrant surroundings.
Guest suite in Waukesha
4.98 out of 5 average rating, 81 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.

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, 334 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.

Top Guest favourite
A spacious suite is shown with a comfortable bed against the wall, accompanied by a cozy seating area featuring a gray couch. A decorative wall art piece adds character, while natural light filters in through the window, illuminating the warm wood flooring.
Guest suite in Waukesha
4.95 out of 5 average rating, 42 reviews

Inlaw Suite with Downtown Charm

Unbeatable Historic Downtown location. Duplex-like entry to your key-access 300sf downstairs suite, full kitchen/bath, standard queen bed w/ memory foam mattress. Walk a quiet neighborhood, <1 mile to the art hub of downtown - enjoy the summer farmer's market, or walk along Fox River! Minutes from convenience/department stores/more parks, 10 mins to I-94, <20 min to Pewaukee lake, <30 mins to Milwaukee/ airport/Lake Michigan. *NOTE: Ceiling is 6ft 7 inches.* NOTE: No pets allowed.*

Guest favourite
A single-story ranch-style home is presented, featuring a well-maintained exterior with a light-colored stone façade. Green grass surrounds the property, complemented by neatly trimmed bushes and a paved walkway leading to the front door. The roof is covered with gray shingles under a partly cloudy sky.
Home in Wauwatosa
4.92 out of 5 average rating, 113 reviews

Relax close to everything in Milwaukee

Ranch Style home in a quiet Neighborhood. You will feel at home and comfortable! The home is well maintained and very clean. In the winters you could cozy up to a nice fire upstairs and relax with a glass of wine. Downstairs is a second fireplace you have going and play a game of pool. In The summer you can enjoy the three seasons room, with looking a cup of coffee and look at the planted flower garden. Close to the Wauwatosa village down town. Even closer to Elm Grove Village.

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, 153 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, 219 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?

Popular amenities for Waukesha holiday rentals

When is the best time to visit Waukesha?

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Frequently Asked Questions

  • What are the best places to stay in Waukesha?

    Stays in downtown Waukesha provide easy access to dining, shops, and cultural sites, while neighborhoods near parks appeal to those seeking more outdoor space. Family travelers often opt for residential areas known for their welcoming atmosphere.

  • What are the best things to do in Waukesha with kids?

    Waukesha has playgrounds, creative spaces in parks, and riverfront trails that families often explore. Frame Park’s playground is frequently suggested, and seasonal events create welcoming activities around the city for younger visitors.

  • What are some of the best things to do in Waukesha?

    Explore downtown’s historic architecture, stroll the riverwalk, or visit local art galleries and markets. Frame Park is frequently suggested for garden walks, while area trails appeal to those looking for outdoor activity.

  • How is the weather in Waukesha?

    Waukesha experiences cold winters, with temperatures from 17°F to 36°F (-8°C to 2°C), and warm summers near 65°F to 82°F (18°C to 28°C). Rain is spread across the year, with spring and summer months often seeing higher precipitation. Bring clothing suitable for seasonal changes.

  • When is the best time to visit Waukesha?

    Late spring through early fall is often recommended for comfortable temperatures, blooming parks, and an uptick in community events. Winter travelers can anticipate colder weather and a quieter atmosphere, with opportunities to experience seasonal traditions.

  • What are the best places to visit in Waukesha?

    Frame Park, the Waukesha County Historical Society and Museum, and the city’s downtown riverwalk are some of the most popular sites. Art spaces and local theaters add cultural variety to your visit.

  • What are some hiking trails in Waukesha?

    Walkers and hikers frequently explore the Glacial Drumlin State Trail and Fox River Trail for scenic views and a peaceful atmosphere. Frame Park’s loop also provides a gentle path along gardens and riverbank.

  • What are some family activities we can do in Waukesha?

    Families often enjoy the hands-on exhibits at the local children’s museum, exploring Frame Park’s play areas, or discovering interactive public art downtown. Outdoor spaces around Waukesha provide room for both relaxation and play.

  • What are some of the best day trip ideas from Waukesha?

    Consider exploring the Milwaukee lakefront for museums and public markets, or discover local nature preserves and neighboring small towns with historic charm. Outdoor enthusiasts might seek out regional parks that are known for hiking and lakeside recreation.

  • Are there any pet friendly accommodations available in Waukesha?

    Waukesha has pet-friendly vacation rentals and stays, particularly in downtown and residential neighborhoods. Local parks and walking trails make outings with your dog convenient and enjoyable.

  • What are some local tips for visiting Waukesha?

    Locals frequently recommend checking out seasonal farmers markets and taking a stroll along the riverwalk for community art and historic views. Keep an eye on event calendars for festivals, especially in warmer months.

  • What is Waukesha known for?

    Waukesha is known for its historic downtown, abundance of local parks, and contributions to music history as the birthplace of Les Paul. Community-focused festivals and public art are also key parts of its local identity.

  • What are the best hidden gems to explore in Waukesha?

    Explore Frame Park for scenic riverfront gardens and tranquil walking paths. The city also has local art studios and historic buildings tucked around downtown, which are frequently suggested for visitors interested in culture and architecture.

  • What are the best foods to try in Waukesha?

    Classic Wisconsin cheese curds, locally crafted sausages, and Friday fish fry are frequently suggested. You will also find locally roasted coffee and a variety of baked goods at independent cafes and markets.

  • What should I bring for a trip to Waukesha?

    Pack layers to stay comfortable through variable temperatures, especially between late fall and early spring when it can be chilly. Include waterproof shoes or boots and a rain jacket, as the area experiences periodic rainfall year-round. Outdoor gear is useful for exploring parks or trails around the city.

  • What is the nightlife in Waukesha like?

    Waukesha has a welcoming downtown with live music venues, local breweries, and casual lounges. Evenings are often centered around community gathering spots and seasonal events, creating a relaxed, locally rooted vibe.

  • What are the most popular events or festivals in Waukesha?

    Waukesha has a summer blues festival, weekly concerts in city parks during warmer months, and downtown art walks several times a year. Labor Day weekend and late summer often bring additional community celebrations and outdoor gatherings.

  • Are there family friendly vacation rentals in Waukesha?

    Many vacation rentals in Waukesha accommodate families, especially in quiet residential areas and near parks. Spacious layouts and child-friendly amenities are often available to make family stays comfortable.

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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