Waukesha County Vacations & Trips from ￥290,705
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Top destinations in Waukesha County
Milwaukee
The Latest Waukesha County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
￥294,278
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
A word of warning to others looking to book this hotel. My family and I booked the Old Town location for 3 nights, specifically because of plans we had in that neighborhood and its proximity to the Red/Purple lines for other plans on the far Northside and Evanston. We had opted not to rent a car because of this.
On the MORNING of check-in (as we were boarding our flight to Chicago) I got an email that they could no longer honor our reservation, and they had rebooked us at the Fulton Market location. While they offered to upgrade our suite and refund a small amt of the nightly rate to help with Uber costs, the new location was a huge inconvenience. We couldn't use the CTA as planned and ended up spending quite a bit more $ on Uber than we were compensated for. We also lost a lot of time in transit that we could have spent enjoying our limited time in the city.
While the suite and building amenities are nice, the whole situation was extremely frustrating and disappointing. We would have cancelled the reservation and booked another hotel in a more convenient location if they had given us any advance notice.
A couple of other notes of warning - there was no housekeeping for the 3 days we were there. There was also a Nespresso maker with 4 pods when we arrived, but when we asked for more the next day, they said we had to pay for them. Given how high the nightly rates are for this hotel it's surprising that no daily housekeeping nor coffee is provided.
Reviewed on Sep 16, 2026
Waukesha County Hotel Deals
AmericInn by Wyndham Brookfield
16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
￥12,146
￥14,028 total
Sep 20 - Sep 21
includes taxes & fees
8/10 Very Good! (1,597 reviews)
"I stay at this hotel a couple of times a month and the rooms need an upgrade - - mainly the bathroom. There have been a few hairs on the walls of the tub/shower."
Reviewed on Sep 16, 2026
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
￥13,476
￥15,564 total
Sep 20 - Sep 21
includes taxes & fees
8.4/10 Very Good! (1,181 reviews)
"Property was dirty and didn’t feel very safe. The back door had tape so it wouldn’t lock. The shower filled the bathtub and it didn’t drain well."
Reviewed on Sep 16, 2026
Embassy Suites by Hilton Milwaukee Brookfield
1200 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
￥18,954
￥21,892 total
Sep 27 - Sep 28
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 ￥290,705. 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.
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.
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.
What to do in Waukesha County
Skip the Line: Museum Admission Ticket - Grohmann Museum
￥800
per adult
Milwaukee Brewers Baseball Game at American Family Field
￥9,634
per adult
Milwaukee Food Tour with 5 Local Favorites Tastings & Secret Dish
￥16,328
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
