Wind Point Holiday Rentals

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Holiday Rentals in Wind Point

The Plaza Hotel

3.0 star property
8.6 out of 10, Excellent, (1050)
"Cool little hotel! Old style building but clean and well maintained! Really great, quiet stay!!"
The price is AU$290
includes taxes & fees
2 Dec - 3 Dec
The Plaza Hotel

Heated Pool, Hot Tub, Fishing Pond, Game Room, Events!! Fall Discounts! Weddings

9.8 out of 10, Exceptional, (193)
"Me and 9 of my friends rented this space it was very affordable for all the amenities that it came with. Robert was very responsive to messaging before and during our stay. The property is huge and built for all kinds of activities. Can’t wait to book again! "
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events!! Fall Discounts! Weddings

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

10.0 out of 10, Exceptional, (231)
"I booked this property for a reunion with some old friends, with the intention that we would be spending a lot of time hanging out. This property was perfect for that -- lots of beds and bathrooms. A beautiful view of the lake from the main living area and two of the bedrooms. Lots of amenities/activities including a pool table, ping pong, a fire pit, etc. But perhaps the best feature was the openness of the kitchen/dining room/pool table/family room, which meant that you feel connected to...
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

Historic House, Frank Lloyd Wright-Designed House In Milwaukee, WI

9.6 out of 10, Exceptional, (232)
"Communication with the property manager was excellent. Fabulous opportunity to experience a FLW home. The property could be challenging for seniors because there are no handrails associated with the steps in and outside the house."
Historic House, Frank Lloyd Wright-Designed House In Milwaukee, WI

Walker's Point House Near Downtown Milwaukee

9.8 out of 10, Exceptional, (31)
"We were all very pleased with the property and the owner was very helpful. "
Walker's Point House Near Downtown Milwaukee

MKE Mansion - Both Wings

9.8 out of 10, Exceptional, (12)
"The house is exactly as listed. There were some small functional issues with the house that the landlord responded to immediately. All around great stay. "
The price is AU$2,306
includes taxes & fees
22 Dec - 23 Dec
MKE Mansion - Both Wings

Stunning Lake Michigan Cottage

9.6 out of 10, Exceptional, (25)
"Host was extremely responsive and easy to work with"
Stunning Lake Michigan Cottage

Spacious Walkers Point Gem in Central Milwaukee

9.4 out of 10, Exceptional, (13)
"This house was beautiful. It was an old house with modern updates. Old wood floors. Amazing brick. The beds were all comphy. The water pressure was great. Simple check in and check out. Having a parking space was awesome in that area. The only flaw was there was some night time traffic noise. However each room had fans and earplugs. Super thoughtful someprovidesplugs. "
Spacious Walkers Point Gem in Central Milwaukee

Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms

10.0 out of 10, Exceptional, (15)
"Clean, comfortable home - well stocked & modern."
The price is AU$1,935
includes taxes & fees
13 Dec - 14 Dec
Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms

207- Luxury 3rd Ward Condo - w/ parking / exec/ family

9.8 out of 10, Exceptional, (13)
"The condo itself is beautiful and stylish. The bed was comfortable, and the check-in/check-out process totally seamless. This is a unit in a mixed-use building, which is the only source of notes for me. The Orange theory Fitness below is audible, though not by much, after 7 AM on weekends. And there is a h"
The price is AU$533
includes taxes & fees
29 Nov - 30 Nov
207- Luxury 3rd Ward Condo - w/ parking / exec/ family

The Beach Life!— Newly Renovated Beach Home awaits you!

10.0 out of 10, Exceptional, (27)
"Very clean and nicely furnished. Great supplies in kitchen and bath. Very responsive host "
The Beach Life!— Newly Renovated Beach Home awaits you!

Enjoy Beachfront Living With family!

9.8 out of 10, Exceptional, (69)
"Beautiful location and view of the lake. Easy access to visiting the area."
Enjoy Beachfront Living With family!

Lake Michigan Vacation Rental w/ Private Beach!

5.4 out of 10, (3)
"Our family of 8 stayed over the weekend at this property. The house is bigger than it looks. There is many different spaces in this home. Not everything is perfect but that is the charm of this old farm house. If you plan to use the yard make sure that it is taken care of before you stay at the property. There are several great places to go less than 20 mins away. We enjoyed the say and this a great place for a large group."
Lake Michigan Vacation Rental w/ Private Beach!

Lake Michigan Waterfront Designer Villa

10.0 out of 10, Exceptional, (2)
"5 star place .. Beautiful views ... Great communication with owner .. Got to meet him and his family. Highly recommend. Loved so much that we are coming back in a few weeks with the whole family .. : )"
The price is AU$926
includes taxes & fees
2 Dec - 3 Dec
Lake Michigan Waterfront Designer Villa

New! Surfs Up! Pro Cleaned, Self Check in - Sleeps 14

9.4 out of 10, Exceptional, (16)
"This property worked great for us! Everything was as-advertised, and Chris was really accommodating of our needs. Thanks so much."
New! Surfs Up! Pro Cleaned, Self Check in - Sleeps 14

Sunny 3 BR Craftsman Bungalow | Bay View

10.0 out of 10, Exceptional, (24)
"Perfect location for MKE and the shops and restaurants in Bay View. Beautiful walkable neighborhood with so many restaurants and coffee shops to discover. House was well appointed and had a terrific backyard set-up. "
Sunny 3 BR Craftsman Bungalow | Bay View

5-Bedroom Sleeps up to 12 + Spacious!

9.4 out of 10, Exceptional, (21)
"Overall, the property was close to the locations that we needed, the property manager was very responsive and responded quickly to the questions that we had. The property was clean and accurate as listed. The backyard was large and the kids enjoyed playing there. If I had to give a couple areas of improvement/feedback, I would say larger beds and more comfortable mattresses would have made a great stay even better. Overall, very satisfied!"
5-Bedroom Sleeps up to 12 + Spacious!

Stylish Residence: 5 Min to Downtown + Pet Friendly

9.6 out of 10, Exceptional, (5)
"Perfect little place for a girls getaway. Had great space and conveniently located. Host was very responsive!"
Stylish Residence: 5 Min to Downtown + Pet Friendly

Modern Lakeside Villa

10.0 out of 10, Exceptional, (15)
"Great home and beautiful location. Thank you!"
Modern Lakeside Villa

Nautical Splash Pad

10.0 out of 10, Exceptional, (2)
"Home was cute and clean. Comfy beds. But the pool steals the show. We will be back!"
Nautical Splash Pad
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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Other types of properties in Wind Point you may be interested in

Hilton Milwaukee

4.0 star property
8.2 out of 10, Very good, (1037)
"Was very convenient to be a vendor at the convention center."
The price is AU$168
includes taxes & fees
22 Dec - 23 Dec
Hilton Milwaukee

Saint Kate - The Arts Hotel

4.0 star property
9.8 out of 10, Exceptional, (1974)
"The art and ambiance are unlike any hotel I've stayed at. Loved the record player, the colored pencils/butcher paper, all of it. Fantastic staff as well."
The price is AU$234
includes taxes & fees
16 Dec - 17 Dec
Saint Kate - The Arts Hotel

The Pfister Hotel

4.5 star property
9.4 out of 10, Exceptional, (1540)
"The Pfister never disappoints. Hotel is managed well as you always see the same friendly faces year after year. Special shout out to Dimorco, Dragonica, and Vlad. Super comfortable beds, quiet, and clean!"
The price is AU$243
includes taxes & fees
5 Dec - 6 Dec
The Pfister Hotel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Heated Pool, Hot Tub, Fishing Pond, Game Room, Events!! Fall Discounts! Weddings: This holiday home rental outside of Wind Point is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 3 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 balcony, a garden and a selection of games 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. Wingspread and Wind Point Lighthouse 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.