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Holiday Rentals in Wind Point

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Our top choices for Wind Point holiday rentals

9.6 out of 10, Exceptional, (87)
"Our room was perfect for our weekend visit with friends who lived nearby. The room had everything we needed and was very close to the lake, which has a lovely walking path. Our hosts were kind and helpful."
United States
Julia H.
The price is €97
includes taxes & fees
29 Dec - 30 Dec
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Aparthotel in Downtown Milwaukee

The Plaza Hotel
3.0 star property
8.8 out of 10, Excellent, (1153)
"From check in to check out excellent stay!"
United States
Heather
The price is €144
includes taxes & fees
18 Jan - 19 Jan 2026
The Plaza Hotel

Apartment in Racine

Welcome To My Loft!
10.0 out of 10, Exceptional, (16)
"Great place to stay!"
United States
kathleen
The price is €98
includes taxes & fees
31 Dec - 1 Jan 2026
Welcome To My Loft!
9.0 out of 10, Wonderful, (16)
"This is a lovely place to stay…it’s cozy, well-stocked and located right near the beach (Lake Michigan). We had a wonderful week here! "
United States
Robert D.
The price is €260
includes taxes & fees
4 Jan - 5 Jan 2026
Beach Lake Michigan King Bed Pet Friendly
9.2 out of 10, Wonderful, (34)
"Great location near the beach, good kitchen, large fenced yard with lots of seating options, good communication with host"
United States
Donald N.
The price is €230
includes taxes & fees
20 Jan - 21 Jan 2026
3-bedroom vacation home just a short walk to Lake Michigan

Apartment in Racine

Wisconsin Treehouse Getaway!
9.6 out of 10, Exceptional, (26)
"We had a wonderful time staying here while visiting the surrounding area!"
United States
Collin C.
The price is €213
includes taxes & fees
29 Dec - 30 Dec
Wisconsin Treehouse Getaway!
10.0 out of 10, Exceptional, (13)
"Awesome house with a fantastic beach! The whole group had a wonderful time "
United States
Nate L.
The price is €554
includes taxes & fees
6 Jan - 7 Jan 2026
Lake Michigan Waterfront Designer Villa
10.0 out of 10, Exceptional, (7)
"Charming apartment, convenient location"
United States
Ashton G.
The price is €172
includes taxes & fees
13 Jan - 14 Jan 2026
KK lower · Funky 2BR in Prime Bay View - w/ Parking
10.0 out of 10, Exceptional, (11)
"was great and close to our daughter"
United States
Nicholas S.
The price is €345
includes taxes & fees
29 Dec - 30 Dec
Whole House in Bay View + Fenced-in Yard + Parking
10.0 out of 10, Exceptional, (2)
"Room was spotless and had great amenities. Great location. "
United States
Philip
The price is €106
includes taxes & fees
4 Jan - 5 Jan 2026
Deer District Studio Apt - One Block from Fiserv and Baird

Apartment in Downtown Milwaukee

Downtown Luxury 2BR Penthouse Apt
2.0 star property
10.0 out of 10, Exceptional, (6)
"What an awesome location, we’ll definitely be back. The place was perfect!"
United States
Justin G.
The price is €138
includes taxes & fees
4 Jan - 5 Jan 2026
Downtown Luxury 2BR Penthouse Apt

Apartment in Fifth Ward

Stylish Apt in Walker's Point
10.0 out of 10, Exceptional, (4)
"I loved my stay here! the location is in a good area near downtown milwaukee with lots of food near by! My stay here was great and the host was very responsive and helpful and provided lots of information. Very cute and aesthetic decor, felt very homey! "
United States
Anthony R.
The price is €214
includes taxes & fees
29 Dec - 30 Dec
Stylish Apt in Walker's Point
9.4 out of 10, Exceptional, (15)
"The property is extraordinarily charming and was perfect for a short family visit in mid/late September. It's close to Bayview and is generally a good location for having fun in Milwaukee.I'm bookmarking this place for future visits with family and friends."
United States
Alexander H.
The price is €198
includes taxes & fees
12 Jan - 13 Jan 2026
Potter Lower · Funky 2.5BR in the Heart of Bay View - w/ Parking
10.0 out of 10, Exceptional, (27)
"Very comfortable and convenient to everything downtown."
United States
Reddemann R.
The price is €364
includes taxes & fees
29 Dec - 30 Dec
Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer
2.0 star property
10.0 out of 10, Exceptional, (1)
"Five stars all the way!"
United States
Rob K.
The price is €254
includes taxes & fees
29 Dec - 30 Dec
Historic Walker’s Point Home, Garage & Yard

Holiday Home in Fifth Ward

Whole House in Walker's Point
10.0 out of 10, Exceptional, (1)
Whole House in Walker's Point
9.8 out of 10, Exceptional, (20)
"Great spacious unit in fun and accessible area of the city. We look forward to coming back!"
United States
Chadd
The price is €272
includes taxes & fees
9 Jan - 10 Jan 2026
Unit B- Large Condo w/Patio/ Old World 3rd+Fiserv

Holiday Home in Downtown Milwaukee

Remodeled Home - Steps from Brady Street!
10.0 out of 10, Exceptional, (5)
"Enjoyed stay at this nice home "
United States
Eduardo P.
The price is €230
includes taxes & fees
29 Dec - 30 Dec
Remodeled Home - Steps from Brady Street!
9.8 out of 10, Exceptional, (8)
"Great place to stay"
United States
Jaclyn S.
The price is €278
includes taxes & fees
10 Jan - 11 Jan 2026
301- Condo for 10 by Old World 3rd St/Fiserv Forum
10.0 out of 10, Exceptional, (1)
"Studio was excellent! Absolutely was in a perfect location and equipped with so many nice features such as; coffee, creamer, lint roller, laundry detergent, shampoo/conditioner and much more! The laundry unit was nice to have. Tyler was extremely responsive prior to the trip and during. Thank you!!"
United States
Shannon R.
The price is €202
includes taxes & fees
4 Jan - 5 Jan 2026
Stylish Modern Studio in Vibrant Walker's 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.
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Top Wind Point Hotel Reviews

Find out more about Wind Point

Everything you need to know about Wind Point holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wind Point holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wind Point holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wind Point holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wind Point. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wind Point holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wind Point holiday rentals we have selected for you start as low as €97 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wind Point rentals

At Expedia, we put the best Wind Point holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wind Point rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wind Point holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wind Point. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Wind Point?

Yes, there are holiday rentals close to the most popular sights in Wind Point, or you can select a more secluded option if you're looking for a relaxing stay. Wind Point is known for its monuments.

What are some of the best holiday rentals that Wind Point has to offer?

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft: This holiday home rental outside of Wind Point is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a pool table and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Wind Point?

While exploring the area, visit family-friendly sights like Kenosha Public Museum, or get outside and enjoy nature at Lake Michigan. Wind Point Lighthouse and Wingspread are other places to visit while you're in town.

What’s a holiday rental in Wind Point like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wind Point. Holiday rentals provide amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for family trips or small group gatherings.