
Cottage vacation rentals in Winnetka
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Top-rated cottage rentals in Winnetka
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winnetka cottage rentals
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.

#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.

#3 Charming Lake Cottage - Cypress Resort & Marine
We had a lovely stay at Cottage 3! The cottage was clean, calm, comfortable, and had a beautiful view! It was just a staircase away from the lake which was so helpful with kids. There were kayaks, paddle boards, floats, and much more which provided endless entertainment for us and our kids ranging from 2-11 years old. Amanda was so friendly, great at communication, and always available for whatever we needed. It’s a great place to stay!
Pet-friendly cottage rentals

#2: Cute 2 bedroom cottage on the beach!
This is a small cabin, but well laid out. Be aware that there is a short walk from the busy parking lot, but not over far and it’s an easy path. The cabin is clean, quiet and right on the water. We brought two dogs and they loved the place. There is a water bowl in a cabinet by the door. Nothing to beat it in the area, and Jennifer was nothing but helpful. Would stay again.

Bird House Holiday
Our stay was stress free even despite having a water issue. Kurt was responsive and proactive and it was fixed right away. We appreciated how the situation was handled and plan to stay here in the future.

Waterfront Fox Lake Vacation Rental w/ Fire Pit!
We had an amazing time at this cottage! From the start, the hosts were excellent communicators and all the instructions were clear. When we got there, everything was clean and as described/seen in pictures. The area was beautiful and we absolutely love the scenery and how much we could do at the cottage. By far, the BEST Airbnb we’ve been to- and we’ve been to several. Thanks for having us! We would love to come back.

Nautical Lake Cottage at Petite Lake Resort, #2
This lake cottage was so cute and perfect for our weekend trip! Amanda was a great host and so responsive when we had questions. I’d definitely recommend to anyone in the area!

Klara's Cottage: Yosemite Room
Rachel’s place was perfect for our stay! Really cute home and Rachel was so friendly, helpful, and willing to help with whatever we needed (plus her dogs Schatzi and Chicago were amazing hosts too). The house was fully stocked and bedroom was very nice! We visited for the weekend to explore Chicago and go to a concert and we had a great time. Thank you Rachel!

Driftwood, Cozy Waterfront Cottage, Separate Unit
Our host was fantastic! He called to verify we had all we needed and included some much needed extras for a very nominal charge. We had another Airbnb booked and we were cancelled 10 days before our trip. We rebooked here and this host went above and beyond to make our stay pleasant and took the time to ensure our needs were met after learning of our situation. The home is so clean, modern and well decorated. I can’t say enough how appreciative we are.

Klara's Cottage: Sunshine Room
Phenomenal Super Host ❤️ Thank you for the Incredible Stay, you made my first time in Chicago a very special experience!

Lakefront Cottage w/ Sunset Views
Great place! Would definitely recommend to spend some quality time by the lake.
Private cottage rentals

Lakefront Cottage with Gorgeous Sunsets
Josh is a great host, very responsive. The lakehouse is a cute weekend getaway. The sunsets are gorgeous and the house is cozy and heats up well (we stayed when it was chilly outside).

Charming 1901 cottage blocks away from Bangs Lake.
The house was perfect for our needs. The host was wonderful at making sure we had what we needed for our guests. We were traveling with a 4 year old and a 3 month old and she made sure the home had a high chair, a pack’n’play, and one of the rooms had a Lego set that the 4 year old was thrilled to play with! The upstairs was definitely warm on hot days and nights, but extra fans were provided for each room which was helpful. Overall we enjoyed our stay and felt comfortable.

Lakefront Views, Free Water Sports!!
Very great get away I’m a fisherman and caught some really big fish. Water was clean lots to do on the chain of lakes. Only 9 mins from McDonald’s and Walmart in case anyone needs last minute stuff. Chris and Shannon were very knowledgeable of the area. Great place for peace. Sunset is on bedroom window side. (Loved to see this as I was just getting up) neighbors were friendly. Love the fact we had water toys like paddle boat kayaks and paddle board for use even though I didn’t use them I was fishing my 3 days there. There’s a dock and water at dock is about 2’-3’. Would highly recommended them. Overall it was a great stay and will be coming back again. To all who is looking at this you will love this environment. I consider this place a happy place getaway. Caught cat fish, drum,bass,,walleye Maybe rent a boat and explore the chain of lakes next time. Thank you Shannon and Chris for the great experience

All Season Cozy Cottage
Very cozy comfortable cottage. Enjoyed it!

Twin Lakes Cottage: Walk to Elizabeth Lake!
Our host was friendly, informative, and flexible. She reached out mid-stay to check on us and shared several local recommendations. The house was clean, big, quiet, and homey. We felt welcome. The kitchen was well stocked with pots, pans, dishes, and flatware. Our two families had room to spread out.

Key House at Petite Lake Resort, #4
Amanda sent great information and instructions prior to checking in and was helpful and communicative. Beautiful place, clean, comfortable. Used the fire pit, which was enjoyable. Lots to do outdoors.
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