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Compare 503 Vacation Homes in Winnetka with updated reviews, rates, and availability.

"Perfect location. Home was very comfortable and inviting. Beds and mattresses were heavenly. We thoroughly enjoyed our stay. "

First floor living room with leather couch, smart cable TV, and Alexa speaker.

"We had an amazing time, and this home was a large part of why we enjoyed Chicago so much! The hosts were great, and very responsive to all of our questions! The home was spacious and warm. The perfect location, so close to the train so we could travel back and forth to downtown. The kitchen has a great space for cooking, what a great stove. The ping pong/billiards table was a hit! We would definitely stay here again! "

"Location is great, size of the house is great with queen beds in all room and even one with a King bed. Basement was very cold, ( it’s winter) so that bedroom was not used but wasn’t needed anyways. The house needs a really good cleaning especially the kitchen especially the cabinets. Also coffee maker is tiny, doesn’t make sense considering the size of the house. Ironing board had no cover just metal frame, kitchen was not stocked properly for the size of the house. Loved the fact there was...

Welcome to our guest house, "A Little House on Prairie"!

"Got to stay in this wonderful home while visiting my son and his family. I loved it!"

AED 1,139 total

includes taxes & fees

4 Feb - 5 Feb

"This is the second year we have stayed at this location during Thanksgiving. It is convenient for visiting family members in Park Ridge and Glenview. The four bedrooms and two bathrooms provide the space we need. There is also a well equipped kitchen. "

AED 1,046 total

includes taxes & fees

28 Jan - 29 Jan

"We had unexpected changes last minute for Thanksgiving and our Host was so great and accommodating. The space was roomy and beautiful with the rooms flowing into each other so little groups of people could talk and nosh and enjoy the food and company. The light coming in from the windows and the backyard is a little piece of nature to enjoy. At our request, our wonderful host even snuck in to start a fire for us in the firepit, making it even more homey. My husband, myself, my sister, and my...

"My husband and I spent a week here with our three dogs while in town for a family wedding. I was able to work from home while my husband took the CTA into the Chicago office of his company. The home was lovely and well stocked with everything that we needed for a week away from home. Would highly recommend."

Escape to your private outdoor oasis, available May-October. Lounge on the illuminating sofa, sway in the hammock, gather around the table for 8, fire up the grill – all within the serenity of a fenced-in retreat

"Second time staying at the Riverhouse. Loved it just as much as the first time.The location is terrific...in the city, but plenty of parking. Local mom and pop restaurantaway.walkable."

Libertyville Vacation Rental | 3BR | 3BA | 2,700 Sq Ft | Step-Free Access

"We rented this house to stay for my daughter’s graduation from Navy Boot Camp. It was an easy drive in and ample room for everyone. The host was awesome and attentive to our needs. Honestly, we didn’t really have any needs, but we used party poppers in the house and wanted to be able to clean them up, but we couldn’t find the broom. Being from California, I was super nervous about being cold, but as soon as we walked in the house, it was super warm and felt so cozy. The heated floors are...

"Great house . "

"We had a mini cousin reunion with family who drove in from different states. No one here has a house big enough to have all of us, so this was the perfect option. The house was lovely, neighborhood very nice, easy to get to, and the host was gracious making us feel like we were all at home. I’d give it 10/5 stars if I could!"

"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"

"We had a great time staying here for a family trip. Plenty of space for games, cooking, sleeping, talking. We only used a fraction of what was available. When we had trouble figuring out heating system, host was very responsive. "

"Came to see my son graduate bootcamp"

"We needed a place to sleep with our 3 young adult sons over the Christmas holiday and this place was perfect for that. It is very basic, but also much less expensive than most other places in this area, and in an excellent location. There are 2 coffee shops just around the corner and plenty of restaurants within easy walking distance. The rooms are clean and spacious. The bedroom has blackout curtains and comfortable beds. Seeing that it is located on a fairly busy street, the apartment was very...

"My family gets together every fall. Our first stay in a vacation rental home was in 2015. It is with almost ten years of knowledge that I declare this house one of the best. We had an amazing stay! Craig is wonderful host. This house is filled with all sorts of extras and bonuses. Getting in the house was easy. I can't tell you how many times we stood outside of a house because the code didn't work. We walked through the house oohing and ahhing in each room. Everyone loved watching movies...

AED 3,190 total

includes taxes & fees

27 Jan - 28 Jan

"It was a great house with needed amenities and lots of space. Great location not far from downtown. Host was great to communicate with."

"The house was big enough for whole family. It was also in a great location. However, the locked bedroom doors were a big inconvenience and the carpeting was disgusting. So dirty. Did not like walking in it without shoes."

"The property was exactly as advertised. Great location for our weekend visit. Very comfortable and had everything we needed for a 2 night stay. "

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Other property types in Winnetka

"Amazing view and the apartment space was perfect. There was some cabinets that were banged up pretty good and the garbage disposal/dishwasher were not working but it was such a beautiful place that it didn't even matter. The valet was super helpful as you have to walk around the block and with alot of luggage it wasn't easy. "

AED 581 total

includes taxes & fees

13 Jan - 14 Jan

"Kasa was a pleasant surprise. Based on previous reviews, we understood that this was not a traditional hotel with amenities and had a virtual front desk but we did have an onsite person that did help us check in and store luggage. The apartment style room was very spacious and clean. We enjoyed having the extra space to spread out and the full kitchen was so handy when storing food or leftovers. Also, when we didn’t get utensils with our to go orders- Kasa had us covered. It was a nice home...