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.
Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was CA $1,551, price is now CA $1,259 per person
CA $1,259
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
9.4/10 Exceptional! (459 reviews)
Great place! Perfect myself and one child traveling for work.

Reviewed on May 1, 2026

Lake Lawn Resort

Lake Lawn Resort

3.5 out of 5
Price was CA $2,064, price is now CA $1,749 per person
CA $1,749
per person
Jun 24 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
Beautiful resort. Gorgeous setting and rooms. Especially enjoyed 1878 restaurant and bar setting looking out over the lake. Observed outdoor wedding and indoor venues…lovely.

Reviewed on Apr 26, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $2,115, price is now CA $1,496 per person
CA $1,496
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
9.6/10 Exceptional! (2,080 reviews)
I had a wonderful stay at The Pfister Hotel. The hotel itself is beautiful, the accommodations were comfortable, and the overall service was excellent. I also had the opportunity to dine at the steakhouse, which was a great experience — the food and atmosphere were both outstanding. One of the highlights of the stay was the pool, which really stood out as a very nice amenity and added to the overall enjoyment of the weekend. I appreciated the hospitality and would gladly return for another stay.

Reviewed on May 7, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,777, price is now CA $1,365 per person
CA $1,365
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
9.8/10 Exceptional! (2,629 reviews)
Excellent property!

Reviewed on May 7, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,664, price is now CA $1,383 per person
CA $1,383
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
9.2/10 Wonderful! (1,082 reviews)
We loved our stay .. everything was great. The staff was amazing. The bar and food was wonderful. Would go back again and refer to family & friends

Reviewed on May 8, 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 $127 per night from May 24 to May 25
CA $127
CA $143 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (818 reviews)
Tru is tucked away from main roads - that was funky in the dark. It was difficult to figure out how to use the TV & streaming services, but that's often the case in hotels these days. Everything else was great!

Reviewed on Apr 29, 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 $154 per night from May 24 to May 25
CA $154
CA $174 total
May 24 - May 25
includes taxes & fees
8.8/10 Excellent! (585 reviews)
.

Reviewed on May 6, 2026

Home2 Suites by Hilton Milwaukee Brookfield
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from May 11 to May 12
CA $203
CA $239 total
May 11 - May 12
includes taxes & fees
9.2/10 Wonderful! (1,457 reviews)
Great big rooms at a great price. Totally recommended.

Reviewed on May 7, 2026

Potawatomi Hotel & Casino
See all 1,416 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

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

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

What to do in Waukesha

Small Group Kayak Tour of Skyline in Milwaukee

Small Group Kayak Tour of Skyline in Milwaukee

CA $114
per adult
Small Group Kayak Tour of Skyline in Milwaukee
See all activities in Waukesha

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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.