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.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was CA $1,216, price is now CA $861 per person
CA $861
per person
Dec 12 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,841, price is now CA $1,218 per person
CA $1,218
per person
Dec 12 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), 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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,758, price is now CA $1,180 per person
CA $1,180
per person
Dec 12 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $3,404, price is now CA $2,293 per person
CA $2,293
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) 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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,522, price is now CA $1,031 per person
CA $1,031
per person
Dec 12 - Dec 18
found 1 day ago
Roundtrip non-stop 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.

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 $91 per night
CA $91
CA $105 total
Nov 1 - Nov 2
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 Mayfair Mall and Brookfield Square Mall are located nearby.
Pool
Pet-friendly
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 $114 per night
CA $114
CA $132 total
Oct 13 - Oct 14
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 helpful staff and the clean rooms in our reviews. Popular attractions Mayfair Mall and Brookfield Square Mall are located nearby.
Pool
Breakfast included
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 $151 per night
CA $151
CA $174 total
Nov 8 - Nov 9
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 Mayfair Mall and Brookfield Square Mall are located nearby.
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
The price is CA $174 per night
CA $174
CA $201 total
Nov 1 - Nov 2
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 Mayfair Mall and Brookfield Square Mall are located nearby.
Pool
Breakfast included
Wildwood Lodge

Wildwood Lodge

2.5 out of 5
N14 W24121 Tower Place Pewaukee WI
Free cancellation
Reserve now, pay when you stay
The price is CA $112 per night
CA $112
CA $126 total
Oct 26 - Oct 27
includes taxes & fees
Book a stay at this business-friendly hotel in Pewaukee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions K1 Speed and Center Court Sports Complex are located nearby.
Pool
Hot tub
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 $103 per night
CA $103
CA $116 total
Nov 8 - Nov 9
includes taxes & fees
Stay at this hotel in Brookfield. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions Mayfair Mall and The Corners of Brookfield are located nearby.
Pet-friendly
Parking included
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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 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?
CA $861 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.