Waukesha County Vacation Packages 2026 from $508

Search vacation packages deals in Waukesha County's top destinations

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

Milwaukee

Vacations

A boat on a calm lake with a forested shoreline in the background.

Oconomowoc

Vacations

Waukesha County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$508

per person

Sep 5 - Sep 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

The Pfister Hotel

Downtown Milwaukee

Save 100% on your flight

$1,133

per person

Aug 13 - Aug 17

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Milwaukee (MKE)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Relax with a drink at one of the 3 bars/lounges and enjoy the 24-hour gym.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$557

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$752

per person

Sep 3 - Sep 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$926

per person

Aug 6 - Aug 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Top Waukesha County hotels deals

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$119 total

Jul 5 - Jul 6

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Pet friendly

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$103 total

Jul 2 - Jul 3

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a terrace, and a garden are also offered.

Pool

Pet friendly

The Ingleside Hotel

2810 Golf Road Pewaukee WI

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$134 total

Jul 2 - Jul 3

Total with taxes and fees

A water park and an indoor pool are featured at this traditional hotel. Traveling on business? Take advantage of the 20 conference rooms, free WiFi in public areas, and express check-out. Enjoy the gym and perks like free self parking.

Pool

Pet friendly

Embassy Suites by Hilton Milwaukee Brookfield

1200 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$141 total

Jul 12 - Jul 13

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

Pool

Breakfast included

Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI

1250 S Moorland Rd Brookfield WI

Free Cancellation

$105 nightly

$122 total

Jul 7 - Jul 8

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Studio 6 Extended Stay Milwaukee Brookfield WI

325 N Brookfield Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$86 total

Jul 19 - Jul 20

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A safe deposit box and laundry facilities are also provided.

Pet friendly

Parking included

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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.

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.

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.

See properties

Photos of local treasures

Browse Waukesha County vacation photos for more inspiration

A calm lake with a wooden dock extending into the water, surrounded by trees and a clear sky.

A golf course with a putting green, trees with autumn foliage, and a cloudy sky.

A quarry with a large water body and surrounding greenery.

A mural of a guitar with band members painted on it, mounted on a brick wall with windows in the background.

A garden with various wildflowers, a wooden bridge, and trees in the background.

Frequently asked questions

How much are vacation packages to Waukesha County?

$508 is all you need to spend for an exciting vacation in Waukesha County. Bundle your flights and hotel into a Travelocity package and watch the savings start to pile up. With such good prices, there's never been a better time to travel.

Where can I get the best vacation package deals for Waukesha County?

There are amazing Waukesha County package deals to be scored with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties in all corners of the globe? Keep that in mind when you're ready to cross another destination off your list.

Why should I purchase my Waukesha County vacation bundle with Travelocity?

Whether you're planning an epic vacation or a last-minute trip, we have lots of enticing destinations to choose from at a good price. And on top of that, we provide 24/7 support, superb service and a Price Match Guarantee. Save yourself money and time and reserve your dream vacation now.

Can I save money on my Waukesha County car rental if I combine it with a hotel or flight?

Sure can. And our Waukesha County vacation packages are the perfect way to do it. With just a few clicks you can save cash and time by combining your bookings. Pick up the keys to your rental car then chart your own course. Need to fill your itinerary? Add some activities or experiences to your package and make savings on those too.

Which airport is best for Waukesha County?

General Mitchell Intl. Airport (MKE) and Dane County Regional Airport (MSN) are your top options for jetting to Waukesha County.

What is there to do in Waukesha County?

Waukesha County has hidden surprises around every corner, but make sure you get to Little Muskego Lake and Oconomowoc Arts Center while you're here. These attractions are popular with visitors.