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, 992 reviews
"Quite the architectural charm and the breakfast was excellent. Thumbs up!"
The price is NZ$337
per night
30 Jun - 1 Jul
The Plaza Hotel
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events Allowed! Read Description
9.8 out of 10, Exceptional, 183 reviews
"Our family had a lot of fun! We stayed four nights and three full days to enjoy all the things the property had to offer. :)"
The price is NZ$1,666
per night
25 Jul - 26 Jul
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events Allowed! Read Description
Unique and Charming Private Quarters
10.0 out of 10, Exceptional, 38 reviews
"Sandie was so kind and accommodating! The place was clean and cute!"
The price is NZ$175
per night
27 Jun - 28 Jun
Unique and Charming Private Quarters
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The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
10.0 out of 10, Exceptional, 222 reviews
"Home was perfect for family get together! It had everything we needed and more. Close to a Simon’s beach and restaurants. A+ house with fire pits , volleyball and basketball hoop. Plenty of room to spread out. Lovely. !"
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Historic House, Frank Lloyd Wright-Designed House In Milwaukee, WI
9.8 out of 10, Exceptional, 221 reviews
"Once in a lifetime opportunity to stay in a historic property designed by one of the world’s greatest architects. Very roomy, several sleeping areas, 2 1/2 bathrooms and a responsive, accessible host. Loved it."
Historic House, Frank Lloyd Wright-Designed House In Milwaukee, WI
MKE Mansion - Both Wings
9.8 out of 10, Exceptional, 6 reviews
"Amazing location! Incredible house! Fantastichost!"
The price is NZ$1,865
per night
7 Jul - 8 Jul
MKE Mansion - Both Wings
Spacious Walkers Point Gem in Central Milwaukee
10.0 out of 10, Exceptional, 3 reviews
"Stylishly decorated, great space for a big group."
Spacious Walkers Point Gem in Central Milwaukee
Walker's Point House Near Downtown Milwaukee
9.8 out of 10, Exceptional, 19 reviews
"The house was spotless with very comfortable furnishings. The location makes it very easy to access all the sights in Milwaukee. Good restaurants nearby for takeout. We were within five blocks of the wedding venue. Quick on and off the interstate. Having two bathrooms and a first floor bedroom was great. Being able to park in the garage, rather than on the street was a definite plus! Questions to the host were answered quickly! Although we didn't use it, there is a nice park right across the...
Walker's Point House Near Downtown Milwaukee
Stunning Lake Michigan Cottage
9.6 out of 10, Exceptional, 21 reviews
"From booking to check out everything was smooth and the house was perfect. Wonderful experience and we hope to stay again! Thanks for a perfect spot to make memories."
Stunning Lake Michigan Cottage
Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms
10.0 out of 10, Exceptional, 13 reviews
"Great place for the entire crew. Beautiful spot across from park, great access to our son’s wedding in Bayview and a great house. Owner Kyle was amazing and very accomodating."
The price is NZ$3,299
per night
6 Jul - 7 Jul
Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms
Your Milwaukee Getaway: Perfect for Families & Groups! 6 Minutes from Downtown!
9.6 out of 10, Exceptional, 19 reviews
"House was as advertised. Host was extremely accommodating and helpful. Great stay!"
The price is NZ$1,002
per night
26 Jun - 27 Jun
Your Milwaukee Getaway: Perfect for Families & Groups! 6 Minutes from Downtown!
New! Surfs Up! Pro Cleaned, Self Check in - Sleeps 14
9.0 out of 10, Wonderful, 11 reviews
"Property was updated and clean. Communication with host was perfect. Good location near the lake and walking paths."
New! Surfs Up! Pro Cleaned, Self Check in - Sleeps 14
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
9.6 out of 10, Exceptional, 74 reviews
"Clean and appreciated the Christian atmosphere!!"
The price is NZ$182
per night
25 Jun - 26 Jun
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Enjoy Beachfront Living With family!
9.8 out of 10, Exceptional, 65 reviews
"When we arrived at the property, we were graded by the property managers son was very helpful in the process explaining what was going on with the city water construction construction that was happening when we arrive. Overall, everything was perfect have no complaints. We really enjoyed staying at the property. The views were spectacular and we plan on coming again, thank you so much."
Enjoy Beachfront Living With family!
Modern Lakeside Villa
10.0 out of 10, Exceptional, 11 reviews
"We (wife and I) spent 2 nights here as a get-away/Christmas gift to each other, and it was beyond expectations! The location is in a quiet area and close to Kenosha for the shops and restaurants. The views are stunning, and we spent most of our time watching the waves and enjoying “unplugged” time. The house is beautifully decorated and spacious for two people."
Modern Lakeside Villa
Lake Michigan Vacation Rental w/ Private Beach!
5.4 out of 10, 3 reviews
"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!
Wisconsin Treehouse Getaway!
9.8 out of 10, Exceptional, 18 reviews
"Thank you for allowing us to stay in another of your incredible properties ... Enjoyed a nice getaway with my wife. Beautiful location with a creek running along the back of the property. Look forward to seeing you soon .. Thank you, Will & Brenda"
The price is NZ$434
per night
1 Jul - 2 Jul
Wisconsin Treehouse Getaway!
Fisherman's Net Beachouse - Steps from the Lake!
9.8 out of 10, Exceptional, 8 reviews
"Abey was wonderful to work with! Will definitely stay again"
Fisherman's Net Beachouse - Steps from the Lake!
Sunny 3 BR Craftsman Bungalow | Bay View
10.0 out of 10, Exceptional, 14 reviews
"We were in town for 3 nights, attending a family wedding. The location was very convenient to the airport and Walkers Point where the event took place. It was also pretty close to the Art Museum and the Harley Museum (both worth checking out). The house was clean and neat. It is in a quiet neighborhood close to a beautiful park and has some good restaurants in walking distance. The two off-street parking spaces were nice to have, too."
Sunny 3 BR Craftsman Bungalow | Bay View
5-Bedroom Sleeps up to 12 + Spacious!
9.2 out of 10, Wonderful, 20 reviews
"My brothers and their families flew into town for our father’s funeral. It was a nice place with plenty of room for all of us to stay and be together, and it has a big backyard for the kids to play in."
5-Bedroom Sleeps up to 12 + Spacious!
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See all available 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.

Other types of properties in Wind Point you may be interested in

The Pfister Hotel
4.5 star property
9.4 out of 10, Exceptional, 1,367 reviews
"A fabulous historic hotel worth the splurge. Staff was outstanding, and the views were fantastic. Highly recommend."
The price is NZ$323
per night
26 Jun - 27 Jun
The Pfister Hotel
Saint Kate - The Arts Hotel
4.0 star property
9.8 out of 10, Exceptional, 1,749 reviews
"Loved it!"
The price is NZ$323
per night
1 Jul - 2 Jul
Saint Kate - The Arts Hotel
Hilton Milwaukee City Center
4.0 star property
8.0 out of 10, Very good, 1,008 reviews
"The old charm of the Hotel is beautiful!! Staff was very friendly and helpful and will stay again!!"
The price is NZ$211
per night
1 Jul - 2 Jul
Hilton Milwaukee City Center
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wind Point holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wind Point. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wind Point. Seeing all the best attractions is bound to make you fall in love with Wind Point. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wind Point short-term rentals, that won’t be hard to do.

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 Allowed! Read Description: 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 Racine Zoological Gardens, 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.

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