Search Vacation Homes in Winthrop Harbor

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Vacation Homes in Winthrop Harbor

"We were really looking forward to the stay, and it exceeded our expectations significantly. I appreciate how they turned a small house that could have just been a bit rundown into a very lovely space all around. "

AED 950 total

includes taxes & fees

11 Aug - 12 Aug

"Great experience, lots of cooking materials "

AED 1,128 total

includes taxes & fees

20 Jul - 21 Jul

"The view was spectacular!"

"A small group of friends and I celebrated a birthday for a weekend here, and we loved it! The house is beautifully decorated (great for pictures) and had everything we needed. We loved the record player and backyard space. Thanks Daniel for the great stay!"

"The home was good. We had some problems but nothing major. Will stay again if we happen to go to Chicago again"

"Close to our family and friends. "

"Caleb and family were so welcoming and easy to get a hold of if needed. Location was great for Kenosha and Pleasant Prairie. The apartment was perfect size and with all basic amenities needed. Thanks for a great stay! "

"This was a great experience. Marta was great to work with and responded quickly to my questions before and during the stay. The house was clean and had everything we needed for our stay. The kids enjoyed the games and separate space in the basement. "

AED 2,957 total

includes taxes & fees

29 Jul - 30 Jul

"First of all the place looked just like the pictures which we so appreciate! The property was very clean and had everything you would need! Location was very nice and felt like a very safe neighborhood. I would definitely stay there again as it checked all the boxes. Also, I really appreciated how quickly Karla got back to me every time I had a question. Thanks for a great stay....cheers!"

"Love it. Great place but not for babies or toddlers."

"Enjoyed peaceful time on the lake, house was clean and comfortable. Close to all kinds of food and places we liked to go. Would recommend."

AED 1,798 total

includes taxes & fees

22 Jul - 23 Jul

"Our family gathered to visit our Carthage (Kenosha) student and view a lacrosse game. There was plenty of space for all and the outdoor area was very nice for eating and relaxing. Loved that there were multiple refrigerators, huge islands in the kitchen and a grill. We rented both units and had plenty of space for 12 people."

"Lots of room, great views, and cozy environment! Right across tge street from Lake Michigan!"

"The Best"

"Our family came to visit for our son's Navy Bootcamp Graduation. This house was very comfortable. There were plenty of spaces to relax & visit with each other. The house was well equipped. The host was extremely helpful & friendly. We highly recommend this home!"

"Wonderful and clean home with all that you’ll need for a great getaway! Firepit and outdoor living is on point here!! Would definitely book again!"

"The property was beautiful and had everything we needed to make our stay enjoyable and relaxing. We would stay again if available when we are back in the area for a family gathering "