Waukesha Vacation Packages 2026 from $486

Waukesha flight + hotel vacation packages

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

The Ingleside Hotel

$486

per person

Jan 22 - Jan 24

found 18 hours ago

Roundtrip non-stop flight included

New York (JFK) 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 Iron Horse Hotel

Fifth Ward

$662

per person

Jan 22 - Jan 24

found 18 hours ago

Roundtrip non-stop flight included

New York (JFK) 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.

The Pfister Hotel

Downtown Milwaukee

$598

per person

Jan 22 - Jan 24

found 18 hours ago

Roundtrip non-stop flight included

New York (JFK) 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.

Kinn Guesthouse Bay View

Bay View

$568

per person

Jan 22 - Jan 24

found 18 hours ago

Roundtrip non-stop flight included

New York (JFK) to Milwaukee (MKE)

A restaurant and a bar/lounge are featured at this hotel. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a terrace, and a lobby fireplace are also offered.

County Clare Irish Hotel & Pub

Downtown Milwaukee

$513

per person

Jan 22 - Jan 24

found 18 hours ago

Roundtrip non-stop flight included

New York (JFK) to Milwaukee (MKE)

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free breakfast, free WiFi, and free self parking. Dry cleaning and luggage storage are also provided.

Top Waukesha hotels deals

Baymont by Wyndham Waukesha

2111 E Moreland Blvd Waukesha WI

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$87 total

Nov 13 - Nov 14

Total with taxes and fees

This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Tru By Hilton Milwaukee Brookfield

20925 Watertown Road Waukesha WI

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$101 total

Nov 19 - Nov 20

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

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$99 total

Nov 9 - Nov 10

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 a snack bar/deli are also offered.

Pet friendly

Free WiFi

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$100 total

Nov 8 - Nov 9

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

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$137 total

Nov 15 - Nov 16

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

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$199 nightly

$234 total

Nov 15 - Nov 16

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.

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?

$486 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.