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.
Holiday Inn Express Hotel & Suites Pleasant Prairie-Kenosha by IHG

Holiday Inn Express Hotel & Suites Pleasant Prairie-Kenosha by IHG

2.5 out of 5
Price was CA $654, price is now CA $647 per person
CA $647
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
8.8/10 Excellent! (536 reviews)
Rooms were spacious and clean. Only downside is parking in front is minimal if you park in back and use the entrances available had a hard time using key card and if you went around to the back of hotel you had to exit property and go back around

Reviewed on Jan 16, 2026

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Wind Point Hotel Deals

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 $172 per night from Mar 1 to Mar 2
CA $172
CA $203 total
Mar 1 - Mar 2
includes taxes & fees
9.4/10 Exceptional! (1,927 reviews)
We felt like royalty!

Reviewed on Feb 1, 2026

The Pfister Hotel
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave Milwaukee WI
The price is CA $176 per night from Feb 16 to Feb 17
CA $176
CA $207 total
Feb 16 - Feb 17
includes taxes & fees
9.6/10 Exceptional! (2,542 reviews)
The entire hotel experience felt unique and elevated - amenities, lounge area, check in, decor, etc. While we did enjoy a few Milwaukee attractions outside the hotel, there also wasn’t a need to leave due to a lively bar with entertainment, restaurant, art exhibit, decent coffee station etc.

Reviewed on Jan 29, 2026

Saint Kate - The Arts Hotel
Hilton Milwaukee

Hilton Milwaukee

4 out of 5
509 W Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Feb 12 to Feb 13
CA $144
CA $170 total
Feb 12 - Feb 13
includes taxes & fees
8.4/10 Very Good! (1,111 reviews)
Room was clean but had a musty odor when you first entered

Reviewed on Feb 5, 2026

Hilton Milwaukee
See all 548 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

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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.