Deals on vacations and trips to Waukesha County

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A modern architectural structure with a curved roof and glass facade.

Milwaukee

Vacations
Milwaukee
A boat on a calm lake with a forested shoreline in the background.

Oconomowoc

Vacations
Oconomowoc

Waukesha County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $454, price is now $336 per person
$336
per person
Jan 21 - Jan 23
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This smoke-free hotel includes 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $705, price is now $490 per person
$490
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
Price was $518, price is now $377 per person
$377
per person
Jan 15 - Jan 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and airport drop-off service. You'll appreciate the area shuttle, free self parking, and terrace.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $1,104, price is now $819 per person
$819
per person
Jan 9 - Jan 13
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Baymont by Wyndham Gurnee

Baymont by Wyndham Gurnee

2.5 out of 5
Price was $452, price is now $340 per person
$340
per person
Jan 15 - Jan 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Top Waukesha County hotels deals

AmericInn by Wyndham Brookfield

AmericInn by Wyndham Brookfield

3 out of 5
16865 W Bluemound Rd Brookfield WI
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $93 total per night
$93 total
Nov 9 - Nov 10
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
375 S Moorland Rd Brookfield WI
Free Cancellation
Reserve now, pay when you stay
$87 nightly
The price is $100 total per night
$100 total
Nov 15 - Nov 16
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI

Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI

3 out of 5
1250 S Moorland Rd Brookfield WI
Free Cancellation
$97 nightly
The price is $112 total per night
$112 total
Nov 17 - Nov 18
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Embassy Suites by Hilton Milwaukee Brookfield

Embassy Suites by Hilton Milwaukee Brookfield

3.5 out of 5
1200 S Moorland Rd Brookfield WI
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $141 total per night
$141 total
Nov 15 - Nov 16
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Studio 6 Extended Stay Milwaukee Brookfield WI

Studio 6 Extended Stay Milwaukee Brookfield WI

3 out of 5
325 N Brookfield Rd Brookfield WI
Free Cancellation
Reserve now, pay when you stay
$90 nightly
The price is $102 total per night
$102 total
Nov 18 - Nov 19
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A safe deposit box and laundry facilities are also provided.
Pet friendly
Parking included
The Ingleside Hotel

The Ingleside Hotel

4 out of 5
2810 Golf Road Pewaukee WI
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $134 total per night
$134 total
Nov 8 - Nov 9
Total with taxes and fees
A water park and an indoor pool are featured at this traditional hotel. Traveling on business? Take advantage of the 20 conference rooms, free WiFi in public areas, and express check-out. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
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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.

Stay near popular Waukesha County attractions

The entrance to Veterans Memorial Park with stone archways and flags.

Lac La Belle

9.6/10 (14 reviews)
Commune with nature and explore the great outdoors at Lac La Belle during your travels in Oconomowoc. Visit the shops or attend a sporting event in this relaxing area.
See properties

Photos of local treasures

Browse Waukesha County vacation photos for more inspiration

A historic building with a clock tower, illuminated windows, and a sign for the 'Night at the Museum' event.
A calm lake with a wooden dock extending into the water, surrounded by trees and a clear sky.
A golf course with a putting green, trees with autumn foliage, and a cloudy sky.
A quarry with a large water body and surrounding greenery.
A mural of a guitar with band members painted on it, mounted on a brick wall with windows in the background.

Frequently asked questions

How much are vacation packages to Waukesha County?
$336 is all you need to spend for an exciting vacation in Waukesha County. Bundle your flights and hotel into a Travelocity package and watch the savings start to pile up. With such good prices, there's never been a better time to travel.
Where can I get the best vacation package deals for Waukesha County?
There are amazing Waukesha County package deals to be scored with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties in all corners of the globe? Keep that in mind when you're ready to cross another destination off your list.
Why should I purchase my Waukesha County vacation bundle with Travelocity?
Whether you're planning an epic vacation or a last-minute trip, we have lots of enticing destinations to choose from at a good price. And on top of that, we provide 24/7 support, superb service and a Price Match Guarantee. Save yourself money and time and reserve your dream vacation now.
Can I save money on my Waukesha County car rental if I combine it with a hotel or flight?
Sure can. And our Waukesha County vacation packages are the perfect way to do it. With just a few clicks you can save cash and time by combining your bookings. Pick up the keys to your rental car then chart your own course. Need to fill your itinerary? Add some activities or experiences to your package and make savings on those too.
Which airport is best for Waukesha County?
General Mitchell Intl. Airport (MKE) and Dane County Regional Airport (MSN) are your top options for jetting to Waukesha County.
What is there to do in Waukesha County?
Waukesha County has hidden surprises around every corner, but make sure you get to Little Muskego Lake and Oconomowoc Arts Center while you're here. These attractions are popular with visitors.

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