Book Exclusive Waukesha County Vacation Packages

Choose one or more items to build your trip:

Search vacation packages deals in Waukesha County's top destinations

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

Milwaukee

Vacations
Milwaukee
A calm lake surrounded by autumn-colored trees and a small gazebo.

Hartland

Vacations
Hartland

Waukesha County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Freehand Chicago

Freehand Chicago

4 out of 5
Downtown Chicago
Price was CA $1,288, price is now CA $884 per person
CA $884
per person
Oct 4 - Oct 9
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,129, price is now CA $1,330 per person
CA $1,330
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,563, price is now CA $1,032 per person
CA $1,032
per person
Oct 22 - Oct 25
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,257, price is now CA $1,562 per person
CA $1,562
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $4,074, price is now CA $2,845 per person
CA $2,845
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Top Waukesha County hotels deals

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
The price is CA $142 per night
CA $142
CA $164 total
Aug 6 - Aug 7
includes taxes & fees
Book a stay at this golf hotel in Brookfield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Milwaukee County Zoo and Mayfair Mall are located nearby.
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
The price is CA $112 per night
CA $112
CA $130 total
Aug 3 - Aug 4
includes taxes & fees
Book a stay at this business-friendly hotel in Brookfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Milwaukee County Zoo and Mayfair Mall are located nearby.
Embassy Suites by Hilton Milwaukee Brookfield

Embassy Suites by Hilton Milwaukee Brookfield

3.5 out of 5
1200 S Moorland Rd Brookfield WI
The price is CA $171 per night
CA $171
CA $198 total
Aug 16 - Aug 17
includes taxes & fees
Book a stay at this business-friendly hotel in Brookfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Milwaukee County Zoo and Mayfair Mall are located nearby.
The Ingleside Hotel

The Ingleside Hotel

4 out of 5
2810 Golf Road Pewaukee WI
Free cancellation
Reserve now, pay when you stay
The price is CA $150 per night
CA $150
CA $170 total
Aug 3 - Aug 4
includes taxes & fees
Book a stay at this business-friendly hotel in Pewaukee. Enjoy free WiFi, free parking, and water park access (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Springs Water Park and Pewaukee Golf Club are located nearby.
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
The price is CA $148 per night
CA $148
CA $171 total
Aug 31 - Sep 1
includes taxes & fees
Book a stay at this business-friendly hotel in Brookfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Milwaukee County Zoo and Mayfair Mall are located nearby.
Hilton Garden Inn Milwaukee Brookfield Conference Center, WI

Hilton Garden Inn Milwaukee Brookfield Conference Center, WI

3 out of 5
265 S. Moorland Road Brookfield WI
Free cancellation
Reserve now, pay when you stay
The price is CA $148 per night
CA $148
CA $171 total
Aug 9 - Aug 10
includes taxes & fees
Book a stay at this business-friendly hotel in Brookfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Milwaukee County Zoo and Mayfair Mall are located nearby.
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.

Stay near popular Waukesha County attractions

A plate with ham, scrambled eggs, hash browns, and a slice of bread on a Hollander's branded plate.
Photo by Scott D. Irwin
Open Photo by Scott D. Irwin

The Corners of Brookfield

8.8/10 (131 reviews)
You can browse for the perfect souvenirs at The Corners of Brookfield during your trip to Brookfield. Check out the shops and top-notch restaurants in this family-friendly area.
See properties

Photos of local treasures

Browse Waukesha County vacation photos for more inspiration

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.
A garden with various wildflowers, a wooden bridge, and trees in the background.

Frequently asked questions

How much are vacation packages to Waukesha County?
CA $884 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.