Wind Point Vacation Packages

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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.
DoubleTree by Hilton Milwaukee - Brookfield

DoubleTree by Hilton Milwaukee - Brookfield

4 out of 5
Price was CA $1,054, price is now CA $948 per person
CA $948
per person
Oct 3 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
8.4/10 Very Good! (1,001 reviews)
It was a wonderful experience. The staff was super friendly and kind. We found it kid friendly and felt safe.

Reviewed on Aug. 15, 2025

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
Price was CA $1,414, price is now CA $1,218 per person
CA $1,218
per person
Oct 3 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.4/10 Exceptional! (1,012 reviews)
Clean room and Friendly staff

Reviewed on Aug. 28, 2025

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,298, price is now CA $1,160 per person
CA $1,160
per person
Oct 3 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.8/10 Exceptional! (2,397 reviews)
The hotel itself is unique and still the perfect room for comfort and cleanliness. Easy checkin with a glass of champagne. Loved the lobby bar with great bartenders. Great overall hotel close to many arts opportunities, but especially convenient when attending a show at Pabst Theater. Great experience!

Reviewed on Aug. 26, 2025

Kasa Relax in Your Spacious 1BD Pet Friendly Milwaukee

Kasa Relax in Your Spacious 1BD Pet Friendly Milwaukee

2 out of 5
Westown
Price was CA $1,678, price is now CA $1,523 per person
CA $1,523
per person
Oct 3 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
No reviews
Kasa Pet Friendly Nearby Local Eateries Milwaukee

Kasa Pet Friendly Nearby Local Eateries Milwaukee

2 out of 5
Westown
Price was CA $1,678, price is now CA $1,523 per person
CA $1,523
per person
Oct 3 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
No reviews

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Wind Point Hotel Deals

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 $202 per night from Sep 8 to Sep 9
CA $202
CA $239 total
Sep 8 - Sep 9
includes taxes & fees
Potawatomi Hotel & Casino
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

3 out of 5
700 N. Water Street, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Sep 3 to Sep 4
CA $175
CA $207 total
Sep 3 - Sep 4
includes taxes & fees
Drury Plaza Hotel Milwaukee Downtown
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 $254 per night from Sep 21 to Sep 22
CA $254
CA $300 total
Sep 21 - Sep 22
includes taxes & fees
The Pfister Hotel
See all 547 properties in Wind Point
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Wind Point

Wind Point Lighthouse featuring a lighthouse, flowers and heritage architecture

Wind Point Lighthouse

This historical landmark and fully functioning lighthouse offers a great spot for a summer picnic with views over Lake Michigan.

Wind Point Lighthouse

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.

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