Waukesha Vacation Packages 2026 from $267

Waukesha flight + hotel vacation packages

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

The Ingleside Hotel

$267

per person

Jul 26 - Jul 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Milwaukee (MKE)

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.

The Pfister Hotel

Downtown Milwaukee

Save 100% on your flight

$415

per person

Jul 26 - Jul 29

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Saint Kate - The Arts Hotel

Downtown Milwaukee

Save 100% on your flight

$374

per person

Jul 26 - Jul 29

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

The Iron Horse Hotel

Fifth Ward

Save 100% on your flight

$471

per person

Jul 26 - Jul 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Milwaukee (MKE)

This boutique hotel features 3 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.

Sheraton Milwaukee Brookfield Hotel

$288

per person

Jul 26 - Jul 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Milwaukee (MKE)

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.

Top Waukesha hotels deals

Marriott Milwaukee West

W231n1600 Corporate Ct Waukesha WI

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$126 total

Jun 28 - Jun 29

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

Baymont by Wyndham Waukesha

2111 E Moreland Blvd Waukesha WI

Free Cancellation

Reserve now, pay when you stay

$95 nightly

$107 total

Jul 5 - Jul 6

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

Tru By Hilton Milwaukee Brookfield

20925 Watertown Road Waukesha WI

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$129 total

Jun 28 - Jun 29

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

Home2 Suites by Hilton Milwaukee Brookfield

650 Larry Court Waukesha WI

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$135 total

Jul 5 - Jul 6

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 on-the-go breakfast and free self parking.

Pool

Breakfast included

Cobblestone Hotel & Suites - Waukesha/West Milwaukee

704 N Grand Ave Waukesha WI

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$138 total

Jun 21 - Jun 22

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

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$174 nightly

$205 total

Jul 8 - Jul 9

Total with taxes and fees

Pool

Spa

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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

American Family Field

4.5/5(777 reviews)

Catch an event at American Family Field during your trip to Milwaukee. Attend a baseball game or simply enjoy the lively breweries while you're in the area.

Harley-Davidson Museum

4.5/5(342 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(226 reviews)

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

Frequently asked questions

How much are vacation packages to Waukesha?

$267 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.