Waukesha Vacation Packages 2026 from $571

Waukesha flight + hotel vacation packages

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

Dubbel Dutch

Downtown Milwaukee

$571

per person

Nov 25 - Nov 28

found 15 hours ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

This hotel features self parking and free WiFi in public areas. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Express check-in, express check-out, and luggage storage are also on offer.

The Iron Horse Hotel

Fifth Ward

$608

per person

Nov 25 - Nov 28

found 15 hours ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

This boutique hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Families will appreciate the arcade/game room and onsite laundry facilities. WiFi in public areas is free.

Kinn Guesthouse Downtown

Downtown Milwaukee

$790

per person

Nov 25 - Nov 28

found 15 hours ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference space. Self parking and express check-out are also offered on site.

Potawatomi Hotel & Casino

Menomonee River Valley

$693

per person

Nov 25 - Nov 28

found 15 hours ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

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.

Saint Kate - The Arts Hotel

Downtown Milwaukee

$697

per person

Nov 25 - Nov 28

found 15 hours ago

Roundtrip flight included

Orlando (MCO) to Milwaukee (MKE)

This smoke-free hotel's 3 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and express check-out are also offered.

Top Waukesha hotels deals

Baymont by Wyndham Waukesha

2111 E Moreland Blvd Waukesha WI

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$85 total

Sep 16 - Sep 17

Total with taxes and fees

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

Pool

Breakfast included

Marriott Milwaukee West

W231n1600 Corporate Ct Waukesha WI

$118 nightly

$134 total

Sep 27 - Sep 28

Total with taxes and fees

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

Pool

Hot Tub

Cobblestone Hotel & Suites - Waukesha/West Milwaukee

704 N Grand Ave Waukesha WI

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$147 total

Oct 13 - Oct 14

Total with taxes and fees

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. Enjoy the free self-serve breakfast each morning.

Pool

Breakfast included

Tru By Hilton Milwaukee Brookfield

20925 Watertown Road Waukesha WI

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$120 total

Sep 18 - Sep 19

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

$216 nightly

$255 total

Sep 27 - Sep 28

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. Relax with a drink at one of the 3 bars/lounges and enjoy the 24-hour gym.

Pool

Spa

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$78 nightly

$90 total

Sep 13 - Sep 14

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

Pool

Breakfast 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 attractions

A red metal bridge over a calm river, surrounded by lush green trees and grass.

Fox River Park

8.4/10 (16 reviews)

Explore the great outdoors at Fox River Park, a lovely green space in Waukesha. Experience the lively festivals or attend a sporting event in this family-friendly area.

See properties

Frequently asked questions

How much are vacation packages to Waukesha?

$571 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.