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

A modern architectural structure with a curved roof and glass facade.
FlightsFlightsHotelsHotels

Milwaukee

Milwaukee

Top Waukesha County Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was £1,477, price is now £1,001 per person
£1,001
per person
21 Sept - 28 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
I love the pool and exercise room access, breakfast was amazing

Reviewed on 1 Jul 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was £1,522, price is now £1,125 per person
£1,125
per person
21 Sept - 28 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
Everything was lovely, but for reference the rooms with views on the first 5-6 floors are extremely noisy at night due to traffic etc.. Not the properties fault, although I would have thought there might be noise canceling glass or something like other hotels I've stayed at.

Reviewed on 30 Jun 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,637, price is now £1,236 per person
£1,236
per person
21 Sept - 28 Sept
found 24 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.4/10 Very good! (2,006 reviews)
It was so amazing awesome.

Reviewed on 3 Jul 2026

Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Downtown Chicago
Price was £1,670, price is now £1,295 per person
£1,295
per person
14 Aug - 18 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (873 reviews)
The staff was friendly and helpful. They let us check in early, and I got an upgraded room. Very nice property, I would stay here again.

Reviewed on 2 Jul 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was £2,143, price is now £1,670 per person
£1,670
per person
22 Aug - 29 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.

Reviewed on 2 Jul 2026

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
Fully refundableReserve now, pay when you stay
The price is £81 per night from 5 Jul to 6 Jul
£81
5 Jul - 6 Jul
includes taxes & fees
8.4/10 Very good! (930 reviews)
"Good"

Reviewed on 3 Jul 2026

Sheraton Milwaukee Brookfield Hotel
AmericInn by Wyndham Brookfield

AmericInn by Wyndham Brookfield

3 out of 5
16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is £77 per night from 9 Jul to 10 Jul
£77
9 Jul - 10 Jul
includes taxes & fees
8/10 Very good! (1,375 reviews)
"Convenient location"

Reviewed on 3 Jul 2026

AmericInn by Wyndham Brookfield
The Ingleside Hotel

The Ingleside Hotel

4 out of 5
2810 Golf Road Pewaukee WI
Fully refundableReserve now, pay when you stay
The price is £91 per night from 12 Jul to 13 Jul
£91
12 Jul - 13 Jul
includes taxes & fees
8.6/10 Excellent! (858 reviews)
"Friendly staff and nice hotel."

Reviewed on 2 Jul 2026

The Ingleside Hotel
See all 2,214 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.
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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 £1,001. 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.

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 enjoy retail therapy at The Corners of Brookfield during your stay in Brookfield. Visit the shops and top-notch restaurants in this family-friendly area.
See properties

What to do in Waukesha County

Skip the Line: Museum Admission Ticket - Grohmann Museum

Skip the Line: Museum Admission Ticket - Grohmann Museum

£4
per adult
Skip the Line: Museum Admission Ticket - Grohmann Museum
Milwaukee Morbid Mirrorlight Ghost Tours

Milwaukee Morbid Mirrorlight Ghost Tours

£19
per adult
Milwaukee Morbid Mirrorlight Ghost Tours
Whorin' 20s Walking Tour

Whorin' 20s Walking Tour

£41
per adult
Whorin' 20s Walking Tour
See all activities in Waukesha County

* 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.