Waukesha County Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Waukesha County Vacation Rentals

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

New Berlin WI
$1,610 nightly
The price is $1,819 total per night
$1,819 total
Dec 24 - Dec 25
Total with taxes and fees
Guests of this vacation home enjoy features like an indoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly vacation home include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
Wooded Hills/Indoor Pool/Hot Tub/Arcade

Wooded Hills/Indoor Pool/Hot Tub/Arcade

Sussex WI
Guests of this vacation home enjoy features like an indoor pool, a hot tub, and laundry facilities. Additional amenities include a garden and barbecue grills.
Pool
Hot Tub
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

Caledonia WI
Guests staying at this vacation home enjoy access to a water park, an outdoor pool, and a hot tub. Other amenities at this beach vacation home include an arcade/game room, laundry facilities, and barbecue grills.
Pool
Hot Tub
ROVE LIVING/KL - Malt House

ROVE LIVING/KL - Malt House

4 out of 5
1009 West Juneau Avenue Milwaukee WI
At ROVE LIVING/KL - Malt House, guests have access to a 24-hour gym, laundry facilities, and a garden. Free parking is available if you drive.
Kitchen
Washer
Kasa Westown Milwaukee

Kasa Westown Milwaukee

4 out of 5
840 West Juneau Avenue Milwaukee WI
$173 nightly
The price is $204 total per night
$204 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Guests staying at Kasa Westown Milwaukee enjoy a gym, a rooftop terrace, and free WiFi in public areas. Self parking is available for USD 13 per night. Additional amenities include a business center, an arcade/game room, and express check-out.
Kitchen
Washer
The Plaza Hotel

The Plaza Hotel

3 out of 5
1007 N Cass Street Milwaukee WI
Free Cancellation
Reserve now, pay when you stay
$147 nightly
The price is $174 total per night
$174 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
Guests of The Plaza Hotel enjoy free WiFi in public areas, meeting rooms, and laundry facilities. Self parking is available for USD 15.00 per night. The 24-hour front desk has staff standing by to help with tours/tickets and luggage storage. This smoke-free aparthotel also has a vending machine.
Kitchen
Pet friendly
ROVE LIVING/KB - Prospect

ROVE LIVING/KB - Prospect

3 out of 5
1927 North Prospect Avenue Milwaukee WI
Stay at this apartment in Milwaukee. Enjoy free WiFi and air conditioning. Popular attractions Fiserv Forum and Harley-Davidson Museum are located nearby.
Kitchen
Free WiFi
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

Burlington WI
Guests of this vacation home have access to an indoor pool, a gym, and a sauna. Additional amenities include laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva

Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva

2 out of 5
Lake Geneva WI
This vacation home features a water park and barbecue grills.
Kitchen
Free WiFi
THE ULTIMATE 6 BEDROOM LAKEHOUSE

THE ULTIMATE 6 BEDROOM LAKEHOUSE

Lake Geneva WI
$1,027 nightly
The price is $1,145 total per night
$1,145 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests of this vacation home enjoy a hot tub, laundry facilities, and local meal delivery service. Transportation is made easy with limo/town car service. Friendly staff can provide concierge services, and also offer advice about sightseeing. This smoke-free vacation home also has barbecue grills.
Hot Tub
Kitchen
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
Free Cancellation
Reserve now, pay when you stay
$194 nightly
The price is $216 total per night
$216 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Timber Ridge Lodge and Waterpark features a golf course, a full-service spa, and a free water park. There's free parking and limo/town car service. The 24-hour front desk has multilingual staff ready to assist with luggage storage, concierge services, and securing valuables. Other amenities at this ski aparthotel include an indoor pool, an outdoor pool, and a lazy river.
Pool
Hot Tub
Williams Bay beach cottage with hot tub on 2-acres

Williams Bay beach cottage with hot tub on 2-acres

Delavan WI
Ski-in/ski-out access, a sauna, and a hot tub are featured at this cottage. Other amenities at this ski cottage include an arcade/game room, laundry facilities, and a garden.
Hot Tub
Kitchen
Private Beach & Pier Lake Front w/ Fireplace on Lake Como - Walk to Mars Resort!

Private Beach & Pier Lake Front w/ Fireplace on Lake Como - Walk to Mars Resort!

Lake Geneva WI
Guests of this vacation home enjoy access to a water park, laundry facilities, and barbecue grills. This beach vacation home also has a garden.
Kitchen
Washer
Mill Creek Hotel

Mill Creek Hotel

2.5 out of 5
123 Center Street Lake Geneva WI
$157 nightly
The price is $178 total per night
$178 total
Dec 25 - Dec 26
Total with taxes and fees
At Mill Creek Hotel, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. Free parking is available if you drive. Front-desk staff can answer questions 24/7, and assist with tours or tickets, dry cleaning/laundry, and securing valuables. Additional amenities include a hot tub, express check-out, and free newspapers.
Pool
Hot Tub
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage

Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage

Lake Geneva WI
Guests staying at this vacation home have access to a garden and barbecue grills.
Kitchen
Air conditioning
Lakeside Loft! Updated 2 BR condo/Close to Lodge & GN/Outdoor Pool/Free Parking

Lakeside Loft! Updated 2 BR condo/Close to Lodge & GN/Outdoor Pool/Free Parking

Lake Geneva WI
$312 nightly
The price is $347 total per night
$347 total
Dec 26 - Dec 27
Total with taxes and fees
Guests staying at this condo enjoy features like an outdoor pool.
Pool
Kitchen
Quaint, quiet condo minutes from Lake Geneva

Quaint, quiet condo minutes from Lake Geneva

Lake Geneva WI
$287 nightly
The price is $320 total per night
$320 total
Dec 24 - Dec 25
Total with taxes and fees
Guests staying at this condo enjoy features like a water park, an outdoor pool, and a garden.
Pool
Kitchen
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

Kenosha WI
Guests staying at this vacation home enjoy access to a water park, a gym, and a hot tub. Additional amenities include laundry facilities, a garden, and barbecue grills.
Hot Tub
Kitchen
Don't see what you're looking for?
See all available properties in Waukesha County
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Waukesha County

    Embassy Suites by Hilton Milwaukee Brookfield

    Embassy Suites by Hilton Milwaukee Brookfield

    1200 S Moorland Rd Brookfield WI
    $102 nightly
    The price is $117 total per night from Dec 28 to Dec 29
    $117 total
    Dec 28 - Dec 29
    Total with taxes and fees
    8.8/10 Excellent! (1,031 reviews)
    The Ingleside Hotel

    The Ingleside Hotel

    2810 Golf Road Pewaukee WI
    $119 nightly
    The price is $134 total per night from Jan 5 to Jan 6
    $134 total
    Jan 5 - Jan 6, 2026
    Total with taxes and fees
    8.4/10 Very Good! (759 reviews)
    Sonesta Select Milwaukee Brookfield

    Sonesta Select Milwaukee Brookfield

    16865 W Bluemound Rd Brookfield WI
    $74 nightly
    The price is $85 total per night from Dec 28 to Dec 29
    $85 total
    Dec 28 - Dec 29
    Total with taxes and fees
    8/10 Very Good! (1,367 reviews)

Orbitz makes it easy to find vacation rentals in Waukesha County 

🏠 What is the best price for a Waukesha County vacation rental?


Waukesha County rentals range between $85 and $1,819 per night. At Orbitz, we have a vacation rental for every budget.


🏠 What types of vacation rentals in Waukesha County can I rent?


Choose from apartments to beautifully decorated vacation homes, condo resorts or even B&Bs or motels for your next Waukesha County getaway. Orbitz filters your search results so you can find the best Waukesha County vacation rental for you. We have tons of options.


🏠 Are cancellations free on Waukesha County vacation rentals with Orbitz?


You may be able to cancel or amend your Waukesha County vacation rental booking free of charge before a pre-agreed deadline. Make sure to check the terms of cancellation before you book—so you know exactly where you stand. 


🏠 How do I find the best vacation rental deals in Waukesha County?


Enter your travel dates, and we’ll do the rest. You can then browse our exciting deals and all the tempting vacation rentals we have on offer in Waukesha County by filtering your search by amenities, prices, and property types and look at customers ratings to help you pick.


🏠 How do I cancel my vacation rental booking through Orbitz


Vacation rentals have slightly different rules to other bookings on Orbitz. Usually, you need to contact your property manager, you may be able to get a full refund before the cancellation date. Click My TripsOpens in a new window on your Orbitz account page to find the right information contact. If you need more help, visit our Customer ServiceOpens in a new window page. 


🏠 What are the advantages of booking a vacation rental in Waukesha County?


When you book a Waukesha County vacation rental, you have the privacy of home and can add on those luxury amenities of a hotel. Filter your vacation rental results to find a place with a hot tub or pool, games rooms or large patio with a barbecue. With so much choice on offer, it’s easy to plan the perfect trip with Orbitz. 


🏠 Where can I find vacation rentals in Waukesha County?


Escape back to nature and check out some of the smaller towns. You’ll find great vacation rentals right across Waukesha County—with plenty of hidden gems. We also have plenty of inventory in Waukesha County main cities and near popular attraction spots.


🏠 Why should I book my Waukesha County vacation rental with Orbitz?


At Orbitz, we search the market for the best accommodation, flights, and car rental deals, so you don’t have to. We’ll help you build your dream Waukesha County vacation. With plenty of vacation rentals on offer, you can be sure to find the one that’s right for you in just a few clicks. 


More to Explore