Waukesha Vacation Packages 2025/2026 from $232

Waukesha flight + hotel vacation packages

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

DoubleTree by Hilton Milwaukee - Brookfield

$232

per person

Feb 13 - Feb 15

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

This hotel features an indoor pool, a gym, and a restaurant. 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 perks like free self parking.

Holiday Inn Express Milwaukee West Allis by IHG

West Allis

$350

per person

Dec 23 - Dec 29

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

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. Guests will appreciate freebies like buffet breakfast and free self parking.

Holiday Inn Express Milwaukee Downtown by IHG

Downtown Milwaukee

$306

per person

Feb 13 - Feb 15

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Traveling on business? Take advantage of the 24-hour business center and valet parking. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Kimpton Journeyman Hotel by IHG

Downtown Milwaukee

$379

per person

Feb 13 - Feb 15

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

The hotel's gym, a rooftop terrace, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A restaurant, concierge services, and free newspapers are also provided.

Holiday Inn Express Milwaukee-West Medical Center by IHG

Wauwatosa

$391

per person

Dec 23 - Dec 29

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Traveling for business? Take advantage of the business center, laundry service, and conference space. There's a 24-hour gym on site, and a 24-hour front desk and a snack bar/deli are also provided.

Top Waukesha hotels deals

Tru By Hilton Milwaukee Brookfield

20925 Watertown Road Waukesha WI

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$92 total

Nov 24 - Nov 25

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a convenience store are also provided.

Breakfast included

Pet friendly

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$199 total

Dec 8 - Dec 9

Total with taxes and fees

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. Enjoy the 24-hour gym and visit the 3 bars/lounges and poolside bar for drinks.

Pool

Spa

Hilton Milwaukee

509 W Wisconsin Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$105 total

Nov 30 - Dec 1

Total with taxes and fees

This luxury hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a garden are also offered.

Pet friendly

Free WiFi

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$109 nightly

$129 total

Nov 18 - Nov 19

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.

Pet friendly

Free WiFi

Potawatomi Hotel & Casino

1611 West Canal Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$145 nightly

$171 total

Dec 8 - Dec 9

Total with taxes and fees

A casino, 7 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free valet parking. Free self parking, a 24-hour business center, and a coffee shop are also offered.

Parking included

Free WiFi

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

$110 nightly

$130 total

Nov 26 - Nov 27

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 buffet breakfast each morning.

Pool

Hot Tub

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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.

Popular places to visit

Harley-Davidson Museum

4.5/5(337 reviews)

Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.

Milwaukee County Zoo

4.5/5(217 reviews)

This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.

Milwaukee Art Museum

4.5/5(400 reviews)

Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.

Frequently asked questions

How much are vacation packages to Waukesha?

$232 is all you'll need for an unforgettable vacation in Waukesha. Bundle your hotel and flights into a vacation package with Travelocity and see your savings start to pile up. With prices this good, it's never been easier to travel!

How long should my Waukesha vacation be?

If you're looking for some guidance, most visitors spend around 2 nights in Waukesha. But to uncover the true essence of this place, stay a few extra days. You'll be able to get to more attractions and really experience the local vibe.

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

Head straight to Travelocity. With access to 400 air carriers and 1,000,000 worldwide properties, selecting the perfect Waukesha package deal couldn't be simpler.

Why should I book my Waukesha vacation package via Travelocity?

Whether you're on the hunt for the ultimate unplugged vacation or you crave the fun and excitement that only a big city can provide, booking everything with Travelocity saves you time, hassle and money. No need to sift through hundreds of different websites to find the best deal — our Price Match Guarantee ensures you'll always score the lowest possible price, and our team of customer service experts are available 24/7 should you need them.

Will I save money on my Waukesha car rental if I book it with a hotel or flight?

Certainly — combine your car, hotel and flight into a Waukesha vacation package and you can save tons. With so much to discover in Waukesha, that set of wheels will more than come in handy. Once you're in the driver's seat, turn up the stereo and cruise toward Wrigley Field, a top sight about 80 mi from Waukesha.

Which airport is best for Waukesha?

General Mitchell Intl. Airport (MKE), 17 mi east of the city center, is where many people begin their Waukesha adventures. But it's possible that Dane County Regional Airport (MSN) (55 mi away from central Waukesha) could suit you better.

What is there to do in Waukesha?

Waukesha is teeming with places to explore, including Center Court Sports Complex and Infinity Fields Baseball Park. These well-known attractions top most travelers' travel itineraries.

Where should I stay when visiting Waukesha?

Many people choose to check in to the Tru By Hilton Milwaukee Brookfield. It's sure to be a great base for your Waukesha escape.