Waukesha County Vacation Packages
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Your Waukesha County Vacation
Make organizing your next big adventure quick and easy with a Waukesha County vacation package. Whether it's history, nature or something else that lures you to this destination, our packages will help you discover it all. Two of the top cities to check out during your trip to Waukesha County are Oconomowoc and Mukwonago. When you're ready to stop dreaming and start discovering, Expedia will help turn your Waukesha County vacation into a reality.
Top Waukesha County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG
CA $1,063
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,097 reviews)
This hotel isn't within walking distance of a metro or many convenience stores/restaurants. If that is a prerequisite, then this isn't the hotel for you. However, they do have a restaurant and a decent coffee bar.
It's a short rideshare trip to the closest metro (within 10 minutes). If all you need is proximity to the airport and metro, then it's ideal.
Reviewed on Aug 9, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,534
per person
Oct 20 - Oct 24
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Perfect location, Michigan/Ontario. Room was clean and spacious for my family of three. The lobby and rooftop
Reviewed on Aug 9, 2026
Waukesha County Hotel Deals
AmericInn by Wyndham Brookfield
16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
CA $110
CA $127 total
Aug 16 - Aug 17
includes taxes & fees
8/10 Very good! (1,479 reviews)
"Air conditioning leaked, floor was wet. TV guide was not synced correctly."
Reviewed on Aug 9, 2026
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
CA $155
CA $179 total
Aug 16 - Aug 17
includes taxes & fees
8.4/10 Very good! (1,078 reviews)
"Second time staying here and no resolutions were offered from the 1st stay when I brought to the attention of front desk and corporate that Housekeepers were stealing the hotel robes and slippers out of the closet, room was not properly cleaned, mold in bathrooms,had to go down to front desk each ..."
Reviewed on Aug 9, 2026
Embassy Suites by Hilton Milwaukee Brookfield
1200 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
CA $170
CA $197 total
Aug 16 - Aug 17
includes taxes & fees
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.
Frequently asked questions
How much does a Waukesha County vacation package cost?
Discover the best of Waukesha County from as low as CA $1,063. We offer a wonderful selection of hotels, flights and rental cars to suit your travel style. You can score even better deals when you add a couple of tours or activities to your vacation package.
How do I get a cheap travel package to Waukesha County?
Combine your flight and hotel bookings, add extras such as activities, and save with a Waukesha County vacation package. You won't just pick up awesome discounts on your escape — you'll have plenty of choice too. When you book with Expedia, you can select from more than 550 airlines and 1,000,000 properties throughout the world. Your next big adventure begins right here, right now!
What are the top hotels in Waukesha County?
For properties in Oconomowoc with comfy beds and friendly service, look up Mt. Olympus Water & Theme Park Resort and The Madison Concourse Hotel and Governors Club. If you plan to visit Mukwonago as well, you can look forward to a wonderful night's sleep at Embassy Suites by Hilton Milwaukee Brookfield or La Quinta Inn & Suites by Wyndham Milwaukee SW New Berlin.
How far in advance should I book my Waukesha County vacation?
It depends on the airline, but it's usually possible to browse through international airfares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky travelers will occasionally score a cheaper ticket just weeks before the date of departure.
What does an Expedia Waukesha County travel package include?
That mostly depends on you. You can choose from a range of Waukesha County packages, such as a flight, hotel and rental car. You can also book a flight and a hotel, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like activities and tours. Whatever your ideal Waukesha County vacation looks like, you'll save!
What should I know before booking a Waukesha County travel package?
You'll enjoy amazing savings when you combine your hotels, flights and rental cars into a package. Not just that, booking everything in one place makes trip planning easier. So why waste your money or time? Whether you're putting together a fancy romantic getaway or a low-cost family road trip, browse our vacation packages today.
Can I choose my airline with a Waukesha County Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You can pick and choose your flights, hotels and more. We have access to more than 550 partner airlines all over the world, so you have options galore when arranging your Waukesha County adventure.
If I'm not able to travel, can I cancel my Waukesha County vacation package?
Don't worry if you're rethinking your Waukesha County vacation package — you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We know life can sometimes throw you a curveball, so look up our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.
Stay near popular Waukesha County attractions
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.
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 family-friendly area.
Brookfield Square Mall
8.4/10 (559 reviews)
You can find the perfect gifts to bring home at Brookfield Square Mall during your trip to Brookfield. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Carroll University
8.2/10 (36 reviews)
Enjoy the collegiate vibe when you visit Carroll University, during your trip to Waukesha. Experience the lively festivals or attend a sporting event in this family-friendly area.
Waukesha County Expo Center
8.4/10 (29 reviews)
After visiting Waukesha County Expo Center, make a plan to see the other sights and activities in Waukesha. Experience the lively festivals or attend a sporting event in this family-friendly area.
Harley Davidson Powertrain Operations
7.4/10 (18 reviews)
Harley Davidson Powertrain Operations is just one of the places to see in Menomonee Falls, so why not enjoy the other things to explore during your travels? Experience the lively festivals or attend a sporting event in this family-friendly area.
Old World Wisconsin
9.0/10 (6 reviews)
You can spend time studying the exhibits at Old World Wisconsin during your trip to Eagle. While you're in the area, stroll along the lakeside.
Pewaukee Lake
7.8/10 (25 reviews)
Commune with nature and explore the great outdoors at Pewaukee Lake during your travels in Pewaukee. While in this family-friendly area, you can savor the top-notch restaurants.
What to do in Waukesha County
Milwaukee Food Tour with 5 Local Favorites Tastings & Secret Dish
CA $143
per adult
Milwaukee Historic Downtown Self Guided Walking Tour
CA $14
per adult
Small Group Kayak Tour of Skyline in Milwaukee
CA $117
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
