Waukesha County Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Level Chicago Fulton Market
Downtown Chicago
CA $1,257
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
Great stay in an elegant mostly residential building. Smooth check in, but had to fill out a few forms. Very nice staff. Young building with lots of dogs yay!
Reviewed on Sep 24, 2026
Waukesha County Hotel Deals
AmericInn by Wyndham Brookfield
16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
CA $113
CA $130 total
Sep 27 - Sep 28
includes taxes & fees
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
CA $106
CA $122 total
Oct 18 - Oct 19
includes taxes & fees
The Ingleside Hotel
2810 Golf Road Pewaukee WI
CA $151
CA $170 total
Sep 27 - Sep 28
includes taxes & fees
8.6/10 Excellent! (952 reviews)
"Great hotel."
Reviewed on Sep 24, 2026
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 $1,137. 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
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.
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.
Pewaukee Lake Beach
8.2/10 (36 reviews)
If a restful vacation is part of your travel plans, Pewaukee Lake Beach might be the perfect place to seek out during your trip to Pewaukee.
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.
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.
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.
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.
What to do in Waukesha County
Milwaukee Food Tour with 5 Local Favorites Tastings & Secret Dish
CA $141
per adult
Milwaukee Historic Downtown Self Guided Walking Tour
CA $14
per adult
Small Group Kayak Tour of Skyline in Milwaukee
CA $115
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
