
Cottage holiday rentals in Wind Point
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Top-rated cottage rentals in Wind Point
Guests agree: these cottages are highly rated for location, cleanliness and more.
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Popular amenities for cottage rentals in Wind Point
Cottage rentals with a hot tub

The Coral Cottage
I loved the home , our stay was very nice and peaceful experience being. The host was very kind and flexible with our needs ! Very happy with our stay !

The Yellow Cottage @ Cottages on Petite Lake
great place and I loved being able to bring our dogs. they loved the gated yard to run around in while we chilled in the hot tub. we'd love to visit sometime in the summer to check out more of the lake activities.

#4 Adorable Lake Cottage-Cypress Resort & Marine
This was our second visit to Amanda’s and just like the first time, it left my boys with fun memories. We will be back next summer.

Lakeside Pewaukee Cottage
We were impressed by the cleanliness and open feeling of the place. It was a little smaller than we expected and had very limited seating but fit our group of 3 ok. I can’t imagine it being comfortable for a larger group though unless you’re only using the place to sleep! Overall it was a pleasant experience, beds were comfortable, kitchen well-appointed and the hot tub was nice, but we did feel that the price, once the cleaning fee was added on, was a little steep.

#8 Hillside Cottage at Cypress Resort & Marine
This was my second time staying at this lakehouse, and it was just as great as I remembered. I absolutely love the peaceful surrounding area—it's a perfect spot to relax and enjoy nature. The hosts were very responsive and helpful, answering any questions I had right away. Everything in the listing was exactly as described, and the check-in instructions were clear and easy to follow. The house was clean, comfortable, and had everything I needed. I’m already looking forward to coming back again!

The Blue Roof Cottage @ Cottages on Petite Lake
David was great, cabin lovely, peaceful surroundings. We will definitely be back!

#4 The Cozy Cottage
The place was beautiful. The house is a bit old but we didn’t mind it, it made it feel homey in a way. My friends and I loved the hot tub, would love to come back again.

#3 The Little Blue Cottage @ The Cottages on Petit
Love the rustic feel of the place, easily accessible amenities. Small and intimate, but also enough room for a couple.
Pet-friendly cottage rentals

The Butterfly Cottage
We took our family on a long weekend vacation to explore Lake Geneva and this was such a perfect lake side cottage that was only 20 mins from Lake Geneva. It was so nice to come home to a quiet spot to fish and relax. The cabin is so clean, cozy, cute and had more then everything we needed.

Private 3 bedroom lake house
Awesome place. We will be back!

Twin Lakes Bungalow
Stayed 3 nights to visit family in area. Cute, cozy, and, quiet area that fit our needs perfectly. Everything you need in house for a longer stay and, everything was really clean upon entering house! Beds were comfortable too! The backyard was great for our german shep to play ball, which it's so hard to do when staying in a hotel. Jess was very responsive, super friendly and a pleasure to deal with! Convenient location and walkable to downtown and the shops! Would definitely stay again! :)

Charming Lakeside Cottage
We had a wonderful stay at Jenna’s place. A perfect location on the lake, fantastic backyard and plenty of amenities. Would definitely love to return!

A vintage charming 2-bedroom cottage!
I had a wonderful stay at this beautiful, historic cottage and would highly recommend it. The host has thought of everything to make your experience one full of beauty, comfort, fun, relaxation and ease. As a writer and artist looking for a small town, private retreat, it was a perfect location and living experience, very inspiring and productive. Williams Bay is charming, with great local services including a convenient yoga studio, grocery and salon--all within walking distance of the gorgeous lakefront. This is a gem.

Cottage Escape near Private Browns Lake Beach
The cottage was fabulous. From the moment we opened the front door, it had such a positive vibe! It was clean and bright. Very inviting. Also two awesome workspaces. — as I found myself having to set up my work laptop while I was there. The outdoor space was very inviting with fabulous places to swing and listen to the birds. The private beach was quite the added surprise! Spectacular view of sunsets over the water. So peaceful!

Hilltop Cottage
Quite neighborhood and a beautiful place. Very nice place.

Cozy 2 bedroom cottage on lake Delavan with kayaks
Had a great stay! Place was beautiful and the location was great! Tiffany was very responsive :) The second bedroom was smaller than anticipated but it made sense due to the size of the house. The private beach you have access to is less than a minute walk and we caught some good fish over there. Overall had a great stay and would highly recommend staying here!
Private cottage rentals

Riverfront Cottage/sauna/kayaks/firepit/dock
My daughter and son had to stay for a couple days while we got our floors done and they absolutely loved it. The vibes were amazing, the people were friendly, everything went wonderfully. Thank you for being such amazing hosts and I will of course recommend this place to anyone who needs a peaceful getaway.

Cozy Como Getaway
Super cute place!

Charming Phantom Lake Cottage
We were a group of 4 adults and an 18 month old. Sleeping accommodations were great, plenty of flexibility and comfort. Awesome accommodations for our 18 mos old from high chair to pack and play and even the toys: she had a blast. The home was simply ideal: beautiful, quiet and comfortable. Our host was super responsive and helpful. This was easily one of our best ABNB stays. We visit Wisconsin every year and this will be the first place I will check availability on next year!

Re-imagined 1880s cottage by Highwood, Metra, Lake
Daniel and Jordan’s cottage in Highland Park is wonderful. It is very comfortable for our family of 3 to stay for 10 days. We really like the design and coziness, and it has all the amenities that we need. The neighborhood is very quiet, and it is also within walking distance to a number of restaurants and cafes. Daniel and Jordan are very nice hosts and they are super helpful when we need help and are always responsive. Highly recommend staying at Daniel and Jordan’s place if you are visiting the north shore.

Little Fox Cottage - A Cozy Riverview Getaway
Perfect little Getaway from Me and My Gf’s Work Stressed Life. Responsive host, Clean Kitchen, beautiful view! 10/10⭐️Looking to book this place in the future!

The Green Heron Cottage full kitchen - King bed
The cutest old house ever. So sweet and had all the character you’d want in a house. I have nothing bad to say about the property and I would definitely recommend.

Lake Country Guest Cottage
Fantastic experience in a beautiful area! The place was great for my family and the host even shipped an item we forgot back to us without any issue at all - would highly recommend!

Blue Cottage in the Bay - Walk to beach and shops
Very nice stay! The house was walking distance to a lot of nearby shops/restaurants and accommodated our family nicely. We enjoyed our stay.
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- Six Flags Great America
- Erin Hills Golf Course
- Milwaukee Public Museum
- Alpine Valley Resort
- Geneva National Resort & Club
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