Waukesha County Vacation Packages 2026 from $145

Search vacation packages deals in Waukesha County's top destinations

Milwaukee

Vacations

Waukesha County flight + hotel vacation packages

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

Red Roof Inn PLUS+ Chicago - Willowbrook

$145

per person

Apr 24 - Apr 27

found 10 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A safe deposit box is also provided.

JW Marriott Chicago

Downtown Chicago

Save 100% on your flight

$466

per person

Apr 30 - May 3

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

La Banque Hotel

$395

per person

Apr 23 - Apr 27

found 18 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$580

per person

May 11 - May 14

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Holiday Inn Chicago SW-Countryside ConfCtr by IHG

Save 100% on your flight

$280

per person

Apr 18 - Apr 22

found 7 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking, a garden, and a computer station are also offered.

Top Waukesha County hotels deals

Sonesta Select Milwaukee Brookfield

16865 W Bluemound Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$85 total

Feb 16 - Feb 17

Total with taxes and fees

This hotel features an indoor pool and a 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 lobby fireplace are also offered.

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$85 total

Feb 22 - Feb 23

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, free WiFi in public areas, and free airport shuttle. Enjoy the gym and perks like free self parking.

Wooded Hills/Indoor Pool/Hot Tub/Arcade

Sussex WI

Get rates

This vacation home features an indoor pool and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.

Wildwood Lodge

N14 W24121 Tower Place Pewaukee WI

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$95 total

Feb 16 - Feb 17

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

Embassy Suites by Hilton Milwaukee Brookfield

1200 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$127 total

Mar 12 - Mar 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.

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

1250 S Moorland Rd Brookfield WI

Free Cancellation

$93 nightly

$107 total

Feb 22 - Feb 23

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.

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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.

Photos of local treasures

Browse Waukesha County vacation photos for more inspiration

Looking at the boat launch on Genesee Lake in Waukesha County, Wisconsin. Lazy cumulus clouds are reflected in the calm lake waters.

A meticulously maintained putting green with the flagstick and pin visible, surrounded by lush grass and autumn trees in Waukesha County.

Take the Bugline Trail to see the Lannon Quarry.

These landmarks are throughout town, celebrating the birthplace and burial place of the amazing guitarist/inventor, Les Paul.

Frequently asked questions

How much are vacation packages to Waukesha County?

$145 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.