Waukesha Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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.
Holiday Inn Express Hotel & Suites Milwaukee Airport by IHG
College Heights
Price was CA $1,390, price is now CA $1,123 per person
CA $1,123
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
8/10 Very Good! (975 reviews)
If the dryer is broken and at check in someone asks where the laundry room is at, you should probably mention the dryer is broken! Finding out hours aftet checking in that the dryer is broken is not the time to find out. We wouldve canceled our stay as we needed to wash cloths during our vacation.
Reviewed on Aug. 25, 2025
The Pfister Hotel
Downtown Milwaukee
Price was CA $1,908, price is now CA $1,544 per person
CA $1,544
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.6/10 Exceptional! (1,707 reviews)
Historic, beautiful architecture and stunning interiors in the building. Also food and bar options.
Reviewed on Aug. 30, 2025
Saint Kate - The Arts Hotel
Downtown Milwaukee
Price was CA $1,951, price is now CA $1,580 per person
CA $1,580
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.8/10 Exceptional! (2,397 reviews)
Our first stay at Saint Kate and it will not be our last! Every staff member has been amazing, from chech on to the restaurant and bar. Rooms are lovely, complete with a real record player and ukelele ! Highly recommend this hotel. Best vibes ever!
Reviewed on Aug. 31, 2025
The Iron Horse Hotel
Fifth Ward
Price was CA $1,860, price is now CA $1,519 per person
CA $1,519
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
Always an enjoyable stay @The Ironhorse.. Beds are uber comfortable , love the pillows !
Reviewed on Aug. 27, 2025
Hilton Milwaukee
Westown
Price was CA $1,688, price is now CA $1,387 per person
CA $1,387
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
8.4/10 Very Good! (1,061 reviews)
Our favorite thing about staying there were the adorable pups that greet you! My kids want to go back just for that reason! 😀
Reviewed on Aug. 18, 2025
Waukesha Hotel Deals
Comfort Inn
2510 Plaza Court, Waukesha, WI
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Sep 8 to Sep 9
CA $110
CA $124 total
Sep 8 - Sep 9
includes taxes & fees
Marriott Milwaukee West
W231n1600 Corporate Ct, Waukesha, WI
The price is CA $174 per night from Sep 7 to Sep 8
CA $174
CA $197 total
Sep 7 - Sep 8
includes taxes & fees
The Pfister Hotel
424 E Wisconsin Ave, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $254 per night from Oct 2 to Oct 3
CA $254
CA $300 total
Oct 2 - Oct 3
includes taxes & fees
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.
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.