Book Exclusive Waukesha County Vacation Packages

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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.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,078, price is now CA $774 per person
CA $774
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was CA $3,926, price is now CA $2,363 per person
CA $2,363
per person
Sep 20 - Sep 23
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. 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 $8,482, price is now CA $5,353 per person
CA $5,353
per person
Sep 16 - Sep 22
found 24 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,153, price is now CA $1,484 per person
CA $1,484
per person
Sep 20 - Sep 23
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,607, price is now CA $1,824 per person
CA $1,824
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. 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 $146 per night
CA $146
CA $169 total
Jul 19 - Jul 20
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.
Pool
Pet-friendly
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 $152 per night
CA $152
CA $172 total
Jul 9 - Jul 10
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.
Pool
Pet-friendly
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
The price is CA $174 per night
CA $174
CA $200 total
Jul 26 - Jul 27
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 Brookfield Square Mall are located nearby.
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
The price is CA $109 per night
CA $109
CA $123 total
Jul 20 - Jul 21
includes taxes & fees
Stay at this hotel in Brookfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Milwaukee County Zoo and The Corners of Brookfield are located nearby.
Pet-friendly
Parking included
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 $150 per night
CA $150
CA $173 total
Jul 26 - Jul 27
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 Brookfield Square Mall are located nearby.
Pool
Pet-friendly
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street Milwaukee WI
Free cancellation
Reserve now, pay when you stay
The price is CA $220 per night
CA $220
CA $259 total
Jul 9 - Jul 10
includes taxes & fees
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, free parking, and 7 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions American Family Field and Potawatomi Bingo Casino are located nearby.
Parking included
Free WiFi
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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

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 $774 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.