Waukesha Vacation Packages

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Your Waukesha Vacation

Say bye-bye to the stress of planning and hello to a Waukesha vacation package. With your travel details organized before you leave, you can focus on discovering this city, starting with Halls Park, which is great for nature, watersports and views. Every trip to Waukesha needs a well-planned itinerary. Fill yours with big-name attractions like Springs Water Park, Pewaukee Lake and Carroll University. Browse Expedia's wide range of travel options and start organizing your ultimate vacation to Waukesha now.

Top Waukesha Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Milwaukee Airport by IHG

Crowne Plaza Milwaukee Airport by IHG

3.5 out of 5
College Heights
Price was CA $1,325, price is now CA $1,109 per person
CA $1,109
per person
Jun 22 - Jun 25
found 15 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
7.8/10 Good! (1,008 reviews)
Clean room easy smooth check in

Reviewed on Apr 3, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $1,784, price is now CA $1,365 per person
CA $1,365
per person
Jun 22 - Jun 25
found 15 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
9.6/10 Exceptional! (2,047 reviews)
Service was perfect! Strongly recommend the top floor bar! Wonderful views!

Reviewed on Apr 9, 2026

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was CA $1,353, price is now CA $1,116 per person
CA $1,116
per person
Jun 22 - Jun 25
found 15 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
9.4/10 Exceptional! (456 reviews)
The room was very spacious and clean. We loved the convenience of the area and the many amenities es provided on site. The team did an amazing job of communicating with rapid speed.

Reviewed on Mar 23, 2026

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Menomonee River Valley
Price was CA $1,392, price is now CA $1,163 per person
CA $1,163
per person
Jun 22 - Jun 25
found 15 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
9.2/10 Wonderful! (1,417 reviews)
Clean room, nice casino

Reviewed on Apr 3, 2026

Hampton Inn & Suites Milwaukee Downtown

Hampton Inn & Suites Milwaukee Downtown

2.5 out of 5
Westown
Price was CA $1,556, price is now CA $1,305 per person
CA $1,305
per person
Jun 23 - Jun 26
found 15 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Milwaukee (MKE)
6.8/10 (1,004 reviews)
This is our go-to hotel in Milwaukee. Great location for shows. We have stayed here a few times. Parking is very convenient. The parking garage is connected to the hotel. The breakfast is great! Never had a problem. And, its really quiet.

Reviewed on Apr 4, 2026

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Waukesha Hotel Deals

Tru By Hilton Milwaukee Brookfield

Tru By Hilton Milwaukee Brookfield

2.5 out of 5
20925 Watertown Road Waukesha WI
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Apr 16 to Apr 17
CA $129
CA $146 total
Apr 16 - Apr 17
includes taxes & fees
9/10 Wonderful! (798 reviews)
Great place to stay. Very clean and modern.

Reviewed on Mar 23, 2026

Tru By Hilton Milwaukee Brookfield
Home2 Suites by Hilton Milwaukee Brookfield

Home2 Suites by Hilton Milwaukee Brookfield

3 out of 5
650 Larry Court Waukesha WI
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Apr 26 to Apr 27
CA $148
CA $167 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (578 reviews)
Breakfast was really good. The beds were comfortable. I have no complaints about this place. I would definitely come back again when I’m in the area. I would 10/10 recommend!

Reviewed on Apr 1, 2026

Home2 Suites by Hilton Milwaukee Brookfield
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $306 per night from Apr 19 to Apr 20
CA $306
CA $361 total
Apr 19 - Apr 20
includes taxes & fees
9.6/10 Exceptional! (2,053 reviews)
Service was perfect! Strongly recommend the top floor bar! Wonderful views!

Reviewed on Apr 9, 2026

The Pfister Hotel
See all 1,400 properties in Waukesha
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.
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Discover the most popular places to visit in Waukesha

Harley-Davidson Museum

Harley-Davidson Museum

5/5(13 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.

Harley-Davidson Museum
Milwaukee Art Museum

Milwaukee Art Museum

5/5(12 reviews)

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

Milwaukee Art Museum

Potawatomi Bingo Casino

Why not roll the dice with a visit to Potawatomi Bingo Casino during your time in Milwaukee? Attend a sporting event or simply enjoy the lively breweries while you're in the area.

Potawatomi Bingo Casino

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.