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Compare 525 Vacation Homes in Winnetka with updated reviews, rates, and availability.

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
10.0 out of 10, Exceptional, (118)
"We were a group of 20 family members coming from all over the country for a wedding just a few blocks away. There was room for everyone, plus hairdryers, ironing board, iron, etc. needed to prepare for the big day. Target and Aldi, train station, and several coffee shops and restaurants, and parks within close walking distance made this the perfect location. Everyone loved staying here. We had good weather for porch sitting, and gathering outside after dark. Very helpful and available hosts too ...
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
Lincoln Park Living - Suite 2!
10.0 out of 10, Exceptional, (15)
"Quiet and safe area with an L lline station only a few blocks away that made it very easy to get around the city. Lots of food options in the area."
Lincoln Park Living - Suite 2!
Great 3 bedroom rental unit near Logan Square
9.4 out of 10, Exceptional, (20)
"The property owner David, was very quick in answering my questions through email and always answered his phone. The property was very clean. We found everything in order. There were plenty of towels, washclothes and toiletries. There was plenty of hot water for 4 adults. The kitchen had clean and simple utensils for our use. This property came with 2.5 bedrooms all dressed with fitted sheets, top sheets, and a comforter. Two pillows provided and the closets were spacious. The beds were...
Great 3 bedroom rental unit near Logan Square
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
9.8 out of 10, Exceptional, (12)
"Before and throughout the trip the hosts were very responsive and helpful. We fully booked the house and there was plenty of room for us in the common areas and backyard. The neighborhood around also has an excellent coffee shop, bar, and food areas within walking distance. Next time I bring a group to the Bridgeport area I’ll definitely try to book this property again "
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
New Humble Home! - Near Six Flags & Naval Base!!
8.8 out of 10, Excellent, (22)
"The home is very close to base and was clean. The stairs to the second floor are old and not straight which can be a hazard. It worked for what we needed."
New Humble Home! - Near Six Flags & Naval Base!!
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
10.0 out of 10, Exceptional, (2)
"As good as advertised. Plenty of room for our group. Definitely recommend. "
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Charming, luxe, modern home near Naval base, Six flags, Casino, Gurnee Mills
9.8 out of 10, Exceptional, (9)
"It was a quiet and cozy home near Great Lakes RTC. Great location. "
Charming, luxe, modern home near Naval base, Six flags, Casino, Gurnee Mills
Charming 3-bedroom house with AC and WiFi in serene Des Plaines near O’Hare
2.0 star property
6.8 out of 10, (3)
"Quick stat to check on an aging family member."
The price is AED 771
AED 1,202 total
includes taxes & fees
4 Nov 2024 - 5 Nov 2024
Charming 3-bedroom house with AC and WiFi in serene Des Plaines near O’Hare
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
10.0 out of 10, Exceptional, (32)
"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. "
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
New Your Home Away From Home! - Near Great Lakes Naval Base!!
9.2 out of 10, Wonderful, (15)
"Close to everything for My Son Graduation . We where less then 5 Miles from the Navy Station. I like that We had 6 Beds for everyone could sleep. The Kitchen was perfect for cooking meals. "
New Your Home Away From Home! - Near Great Lakes Naval Base!!
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
9.8 out of 10, Exceptional, (6)
"This is a very nice property. The only thing I caution is that it’s a 3rd floor walk up (actually on the 4th floor because there is nothing on the ground floor). "
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
Entire Beautiful Grove Home
10.0 out of 10, Exceptional, (4)
"The house was perfect. Family was content with location to base which allowed our soldier to spend more time with us and not have to worry about leaving us too soon to be back on base on time. "
Entire Beautiful Grove Home
Wicker Park Entire House, Private Yard and Parking!
10.0 out of 10, Exceptional, (5)
"We loved this place. It was perfect for our work trip to Chicago. The neighborhood is awesome and the host was very organized and super easy to communicate with. Highly recommend this house!"
Wicker Park Entire House, Private Yard and Parking!
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (79)
"Wish every stay was like this. Everything as As advertised and communication simple and open. Pleasure "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.0 out of 10, Wonderful, (19)
"Great space for me and my friends. Nice little porch as well. The one bedroom without the window unit gets very hot.. even with all the fans going. Other than that.. great place to stay! "
The price is AED 588
AED 1,028 total
includes taxes & fees
4 Nov 2024 - 5 Nov 2024
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Roxan Corner
8.6 out of 10, Excellent, (26)
"The pics did not mislead. It was nice and roomy for my guests and I. It could’ve been cleaner but overall enjoyed the house"
Roxan Corner
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
9.6 out of 10, Exceptional, (79)
"This Old Town property was an excellent base for walking exploration of Lincoln Park (Saturday Farmer's Market was fantastic!) and Old Town itself (lively, with very good food, residential neighborhoods, shops, and entertainment), and had easy access to CTA trains to the Loop, Riverwalk, Millennium Park, and much more, had we had time. 7 adults (seniors) spent four nights, and found the four bedrooms, four bathrooms, large fully-equipped kitchen, and living/dining room/patio provided plenty of...
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Spacious 5 BR / King Size Beds + Private Parking!
9.6 out of 10, Exceptional, (8)
"My coworkers and I came to Chicago for a conference and this was the perfect place to stay for it. The rooms were well separated so noise didn't travel between them, and the house was clean and comfortable. The host was extremely accommodating, and it was only a short distance from downtown Chicago."
Spacious 5 BR / King Size Beds + Private Parking!
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
9.2 out of 10, Wonderful, (7)
"The house was excellent for our family. It was definitely enough room and everything was okay for our trip. Neighborhood was nice and no one bothered us. "
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
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.
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Other property types in Winnetka

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (576)
"Very nice place - great location"
The price is AED 459
AED 647 total
includes taxes & fees
11 Nov 2024 - 12 Nov 2024
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.8 out of 10, Excellent, (193)
"Not a lot of self cook food stores nearby "
The price is AED 256
AED 300 total
includes taxes & fees
25 Nov 2024 - 26 Nov 2024
Sonder Market Hall
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (387)
"The apartment was nice. Maybe put a full length mirror in one of the bathrooms….when woman go out they want to look at themselves dressed up for an evening out. "
The price is AED 507
AED 595 total
includes taxes & fees
25 Nov 2024 - 26 Nov 2024
Sonder South Wabash
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.