Waukesha County Holidays

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Your Waukesha County Holiday

Make organising your next big adventure quick and easy with a Waukesha County holiday 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 holiday into a reality.

Top destinations in Waukesha County

Milwaukee Art Museum showing modern architecture and art
FlightsFlightsHotelsHotels

Milwaukee

Milwaukee

Top Waukesha County Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
2 Oct - 9 Oct
found 24 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 Jul 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
1 Oct - 11 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Bed was comfortable, everyone on the front desk team that i interacted with were great. I hope to be back someday.

Reviewed on 13 Aug 2025

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
1 Oct - 11 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (1,156 reviews)
Loved staying at this hotel! This was our second time and we enjoyed it. Super easy to get everywhere and can walk downtown. Would definitely stay here again

Reviewed on 13 Aug 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
1 Oct - 11 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
I think that 67 dollars is a lot for a day of parking, but I guess it’s city’s fault.

Reviewed on 12 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
17 Sept - 22 Sept
found 12 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Waukesha County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
General Mitchell Intl. Airport (MKE)
Top Sights
Kettle Moraine Ranch, Fowler Lake Park and Little Muskego Lake

Top hotels in Waukesha County

Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
375 S Moorland Rd, Brookfield, WI
The price is £74 per night from 24 Aug to 25 Aug
£74
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very Good! (387 reviews)
"Comfortable beds and clean hotel"

Reviewed on 13 Aug 2025

Sheraton Milwaukee Brookfield Hotel
Sonesta Select Milwaukee Brookfield

Sonesta Select Milwaukee Brookfield

3 out of 5
16865 W Bluemound Rd, Brookfield, WI
The price is £74 per night from 19 Aug to 20 Aug
£74
19 Aug - 20 Aug
includes taxes & fees
8/10 Very Good! (1,247 reviews)
"The hotel was great. The only issue was checkin. System was down and it didn’t come back up. One staff member said he couldn’t do anything until system was back up - which it still was not up 8 hours later. One staff member did allow us to check in manually thankfo."

Reviewed on 11 Aug 2025

Sonesta Select Milwaukee Brookfield
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
The price is £87 per night from 1 Sept to 2 Sept
£87
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,070 reviews)
"Briann at the front desk was amazing!"

Reviewed on 10 Aug 2025

Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI
See all 2,292 properties in Waukesha County
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Waukesha County travel package cost?
Say yes to new adventures with our Waukesha County travel packages, which start from a low £1,074. Choose the hotels and flights that suit your plans. Then, add on a couple of enriching experiences for a one-of-a-kind adventure.
If I'm not able to travel, can I cancel my Waukesha County travel package?
Don't worry if you're rethinking your Waukesha County travel package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We totally understand your circumstances can change suddenly, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.
How do I get a cheap travel package to Waukesha County?
Combine your flights and hotels, toss in extras such as activities, and save with a Waukesha County travel package. You won't just walk away with impressive discounts on your getaway — you'll have plenty of choice within your reach too. When you book with Expedia, you'll have your pick of over 550 airlines and 1,000,000 properties around the globe. Your unforgettable holiday begins right here, right now!
Does Expedia offer Book Now, Pay Later Waukesha County holidays?
We certainly do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in instalments. Simply choose the payment plan that suits best during checkout and take away the stress of budgeting for your trip. Remember to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your travel buck. Browse our flexible payment options below:

  • Pay monthly holidays: Klarna has manageable monthly payment plans that suit all budgets, so you can lock in that well-earned holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay for your trip in multiple transactions.
  • Low deposit holidays: When you want to grab an awesome deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock it in.

What are the top hotels in Waukesha County?
For hotels in Oconomowoc with friendly service and cosy beds, you can't beat Brookfield Milwaukee Hotel and Best Western Waukesha Grand. If you're stopping by Mukwonago as well, you can look forward to a relaxing night's sleep at Brookfield Milwaukee Hotel or Best Western Waukesha Grand.
How far in advance should I book my Waukesha County holiday?
While prices fluctuate, we generally advise reserving your seat as soon as possible. Most international fares can be compared on Expedia up to 12 months in advance. If you're booking late, you may still get lucky. Discount prices to Waukesha County sometimes appear just weeks before departure.
What does an Expedia Waukesha County travel package include?
Hotels, rental cars and flights, or any combination of the three — the choice is all yours! Whether you're exploring Waukesha County on a family road trip or travelling with your friends, there's a package to match every style and budget. Once you've made your booking, why not add on some activities?
What should I know before booking a Waukesha County travel package?
You'll score big savings when you bundle your hotels, flights and rental cars into a travel package. Plus, booking everything in one place makes trip planning much easier. So why waste time or money? Whether you're putting together a ritzy romantic getaway or a low-cost family road trip, take a look at our travel packages today.
Can I choose my airline with a Waukesha County Expedia travel package?
With a travel package, you're the one in charge. Whether you'd like to fly to Waukesha County in coach or first class, simply choose from the available airline options. Expedia has access to over 550 airline partners throughout the world.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.