Wind Point Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Photo by Milestone Travels
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Wind Point Vacation
Come and discover this vibrant city for yourself with a Wind Point vacation package. Consider spending some time in the neighborhood of Historic Downtown Racine, which is great for history and culture, and your time here is bound to be unforgettable. If your trip to Wind Point includes a little sightseeing, drop by popular attractions like Wind Point Lighthouse, North Beach Park and Wingspread. Whoever you're going away with and whatever your budget, your dream Wind Point vacation is just a few clicks away with Expedia.
Top Wind Point Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Kinn Guesthouse Bay View
Bay View
Price was CA $1,298, price is now CA $948 per person
CA $948
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.6/10 Exceptional! (428 reviews)
The room was great, location was perfect. I loved the loft vibe and exposed brick. It would have been a 5 star review if the TV was working. We couldn't get the TV to turn on.
Reviewed on Nov 5, 2025
The Iron Horse Hotel
Fifth Ward
Price was CA $1,721, price is now CA $1,236 per person
CA $1,236
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
Staff was great and helpful, food was delicious and the room was amazing!
Reviewed on Feb 9, 2026
Holiday Inn Express Milwaukee Downtown by IHG
Downtown Milwaukee
Price was CA $1,424, price is now CA $1,038 per person
CA $1,038
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9/10 Wonderful! (1,002 reviews)
Room was good for the price however housecleaning was hit or miss and they did not clean the bathroom floor once in the 5 days we were there and on the days they did clean the room, they would forget to empty out the trash cans or left the bathroom sink dirty. Breakfast was just ok, nothing to rave about. The staff day staff was much more helpful than the night staff but both were friendly. The hotel itself is nice and centrally located. We walked almost everywhere.
Reviewed on Jan 27, 2026
Potawatomi Hotel & Casino
Menomonee River Valley
Price was CA $1,399, price is now CA $1,033 per person
CA $1,033
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9/10 Wonderful! (1,357 reviews)
Room was clean and beautiful!! Front desk staff was helpful and has one of the best selections of slot machines in the casino will definitely be going back!!!
Reviewed on Feb 7, 2026
The Brewhouse Inn & Suites
Westown
Price was CA $1,747, price is now CA $1,315 per person
CA $1,315
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.4/10 Exceptional! (1,001 reviews)
Clean room. Greeted with a free beer!
Reviewed on Feb 8, 2026
Wind Point Hotel Deals
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Mar 2 to Mar 3
CA $176
CA $207 total
Mar 2 - Mar 3
includes taxes & fees
9.4/10 Exceptional! (1,936 reviews)
Yes, the room was spotless. The staff members went out of their way to make us feel welcome.
Reviewed on Feb 6, 2026
Saint Kate - The Arts Hotel
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $182 per night from Feb 22 to Feb 23
CA $182
CA $214 total
Feb 22 - Feb 23
includes taxes & fees
9.6/10 Exceptional! (2,550 reviews)
Everything about our stay deserves 5 Stars....from the moment we walked in to the moment we left and everything in between. The staff people we interacted with were nothing short of pleasant & eager to help, the room was not only comfortable, but fun & unique and the art galleries added a special ...
Reviewed on Feb 6, 2026
Drury Plaza Hotel Milwaukee Downtown
700 N. Water Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Feb 16 to Feb 17
CA $137
CA $161 total
Feb 16 - Feb 17
includes taxes & fees
9.6/10 Exceptional! (2,042 reviews)
GREAT HOTEL. You can tell its family owned. Clean. Luxury. The amenities are above and beyond....for instance the complimentary happy hour and light food bites...more like a meal. Staff was super friendly and knowledgeable. After our stay we looked at their other locations so we can be sure to stay ...
Reviewed on Feb 6, 2026
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.
Discover the most popular places to visit in Wind Point
Wind Point Lighthouse
This historical landmark and fully functioning lighthouse offers a great spot for a summer picnic with views over Lake Michigan.
Regency Mall
You can do some window-shopping at Regency Mall during your trip to Racine. Stroll along the area's lakeside or simply enjoy its bars.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
