
Holiday rentals in Waukesha
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Top-rated holiday rentals in Waukesha
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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.

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

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!

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.

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!

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.

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

Lake Country Retreat- Bring Your Boat and Kayaks!
Just steps from the shores of Lake Nagawicka, this cozy home offers the perfect blend of relaxation and adventure. Enjoy a shared pier for kayaking, paddleboarding, or lakeside lounging. Minutes from downtown Delafield and endless activities. Rent from our preferred boat partner or bring your own, boat slip available for minimal cost. Ideal for couples or small families. Whether you’re looking to unwind, explore, or make lasting memories by the water, this inviting getaway has it all.

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.

KING BED/Amazing Location/Free parking/Wi-Fi
Enjoy a fun and relaxing stay with family or friends in this stylish, cozy, and comfortable lower unit, which features: 2 bedrooms (1 king, 1 queen ) 1 bathroom Fully equipped kitchen with dining table and designated coffee bar Living room with a 65” smart TV (Netflix included) Home office space Free parking spot Located just a short drive (4 min) from I94, this home offers easy access to all the city's major attractions * the ideal base for exploring the best of Milwaukee

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.

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.
Popular amenities for Waukesha holiday rentals
Stay near Waukesha's top sights
Other great holiday rentals in Waukesha

3 BR-2Q 2T Beds, 1 bath home walk to State Fair

* NEW* *Black Sheep Cottage*

Next to St Camillus, Froedtert, MCW & Childrens

Peaceful 3 Bedroom Home in Sussex, WI

Beautiful safe quiet home in great location

Cheerful, open space, and relaxing 1 bedroom home.

Lake Country Guest Cottage & Sauna

Brand New Studio w. Private Entry + Garden Patio
When is the best time to visit Waukesha?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $179 SGD | $179 SGD | $179 SGD | $179 SGD | $179 SGD | $179 SGD | $179 SGD | $179 SGD | $179 SGD | $179 SGD | $179 SGD | $179 SGD |
| Avg. temp | -4°C | -3°C | 3°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 12°C | 5°C | -1°C |
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 $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there house rentals with a dedicated workspace in Waukesha?
Yes! Work meets play with ease at over 10 house 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 house rentals in Waukesha?
Waukesha has more than 10 family-friendly house rentals. 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 10 vacation rentals for guests traveling with pets.
Do house rentals in Waukesha have air conditioning?
Absolutely! We offer over 20 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 20 homes with wifi, over 20 homes with air conditioning, 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 $26 SGD per night before taxes and fees

Verified guest reviews
Over 1,480 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
40 of Waukesha holiday rentals include wifi 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
Destinations to explore
- Chicago Holiday rentals
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- Six Flags Great America
- Alpine Valley Resort
- Wilmot Mountain Ski Resort
- Erin Hills Golf Course
- Illinois Beach State Park
- Milwaukee County Zoo
- Milwaukee Public Museum
- Baird Center
- Bradford Beach
- Sunburst
- Discovery World
- Riverside Theater
- Marquette University
- American Family Field
- Fiserv Forum
- Lake Park
- Lake Geneva Cruise Line
- Holy Hill National Shrine of Mary
- Little Switzerland Ski Area
- Lake Geneva Public Library
- Gurnee Mills
- South Shore Park
- Betty Brinn Children's Museum
- Kettle Moraine State Forest - Northern Unit




