Wind Point Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
Price was CA $1,275, price is now CA $989 per person
CA $989
per person
Aug 25 - Aug 29
found 23 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
8.4/10 Very good! (925 reviews)
Room was clean and beds were comfortable Very convenient area with good restaurants nearby Staff very helpful

Reviewed on Jul 10, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $2,231, price is now CA $1,341 per person
CA $1,341
per person
Sep 11 - Sep 14
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.6/10 Exceptional! (2,139 reviews)
Beautiful property. Every staff member--from front desk, bar, restaurant, housekeeping, concierge,to bellhops, were pleasant, professional & helpful. Our room was comfortable, clean & quiet. The location was perfect, just a short walk from the art museum. Would certainly stay here again.

Reviewed on Jul 9, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,330, price is now CA $1,060 per person
CA $1,060
per person
Sep 11 - Sep 14
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.8/10 Exceptional! (2,652 reviews)
Nice clean room. Fun hotel with great food and next to the theatre!

Reviewed on Jul 9, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,293, price is now CA $1,040 per person
CA $1,040
per person
Sep 11 - Sep 14
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.2/10 Wonderful! (1,192 reviews)
No laundry facilities

Reviewed on Jul 10, 2026

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was CA $1,450, price is now CA $1,204 per person
CA $1,204
per person
Sep 11 - Sep 14
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.4/10 Exceptional! (481 reviews)
Great place! Loved that bar and restaurant on site too.

Reviewed on Jul 3, 2026

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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
The price is CA $223 per night from Jul 13 to Jul 14
CA $223
CA $263 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (1,642 reviews)
"The place was a little hard to get to. The staff were very friendly and the room was great."

Reviewed on Jul 10, 2026

Potawatomi Hotel & Casino
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 $313 per night from Jul 26 to Jul 27
CA $313
CA $369 total
Jul 26 - Jul 27
includes taxes & fees
9.6/10 Exceptional! (2,166 reviews)
"Beautiful property. Every staff member--from front desk, bar, restaurant, housekeeping, concierge,to bellhops, were pleasant, professional & helpful. Our room was comfortable, clean & quiet. The location was perfect, just a short walk from the art museum. Would certainly stay here again."

Reviewed on Jul 9, 2026

The Pfister Hotel
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

4 out of 5
700 N. Water Street Milwaukee WI
The price is CA $181 per night from Aug 9 to Aug 10
CA $181
CA $214 total
Aug 9 - Aug 10
includes taxes & fees
9.6/10 Exceptional! (2,307 reviews)
"The reception staff were friendly, professional, and helpful. Our stay was quick but nice. Room was clean, breakfast was good (a lot of options), and parking was easy. The interior of the hotel is beautiful and well preserved. We very much enjoyed our stay and would definitely consider returning ..."

Reviewed on Jul 10, 2026

Drury Plaza Hotel Milwaukee Downtown
See all 605 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
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Stay near popular Wind Point attractions

A white lighthouse with an American flag, surrounded by purple flowers and trees.

Wind Point Lighthouse

8.8/10 (76 reviews)
This historical landmark and fully functioning lighthouse offers a great spot for a summer picnic with views over Lake Michigan.
See properties

Frequently asked questions

How much does a Wind Point vacation package cost?
You can pick up a vacation package to this destination from CA $989 on Expedia. But how much your vacation to Wind Point costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Wind Point?
You can generally find reduced prices and greater availability in January, February and November. Take a look at our cheap Wind Point vacation packages and you could score some great off-season deals.
How many days is enough for Wind Point?
You can see all the top attractions in Wind Point in a few days, including the popular Johnson Wax Headquarters. If you want an extended Wind Point vacation, look at which kind of activities and day tours are available nearby.
Is it worth booking a vacation package to Wind Point?
Wind Point has everything you need for an unforgettable trip. Get your Wind Point vacation off to a flying start by visiting major attractions like Wind Point Lighthouse.
How to find the best Wind Point package deals?
Use Expedia's filter tool to help you find some unbeatable Wind Point package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Wind Point package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Wind Point vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and stays separately. Better still, you can customize your Wind Point escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Wind Point?
If you have your Wind Point vacation dates finalized, book as early as you can to grab some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Wind Point?

  1. Choose your dates: The things you'd like to do in Wind Point and your favourite season will help you decide when to get away.
  2. Budget wisely: On top of the cost of your stay, you should factor in other expenses too. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Wind Point.
  3. Set the duration of your trip: Start by compiling a list of the attractions and activities you want to get to in Wind Point. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick a Wind Point vacation package that brings all your bookings together.

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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.