Winnetka Vacation Rentals

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Browse Select Winnetka Vacation Homes

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

7.8 out of 10, Good, (6)
"The house was immaculate and very spacious. Beautifully decorated. The neighborhood was easy to get in and out of and close enough to downtown. Would highly recommend."
The price is CA $206
CA $338 total
includes taxes & fees
Aug 24 - Aug 25
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

6.0 out of 10, (2)
"Great space for large groups. Park across the street is a great "feature"."
The price is CA $302
CA $1,372 total
includes taxes & fees
Sep 3 - Sep 4
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

9.6 out of 10, Exceptional, (4)
"Home was cute and as advertised, outdoor area great for families to relax. Only recommendation to have some information at the home for guests in the event the alarm system is activated so it can be acknowledged quickly. "
North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi

8.0 out of 10, Very good, (3)
"Only complaint was the fact that the yard was not cut and the grass needed to maintained"
The price is CA $304
CA $620 total
includes taxes & fees
Sep 9 - Sep 10
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi

4BR Retreat w/ Theater, Game Room & Backyard

8.8 out of 10, Excellent, (6)
The price is CA $96
CA $713 total
includes taxes & fees
Aug 26 - Aug 27
4BR Retreat w/ Theater, Game Room & Backyard

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (52)
"Cozy place to stay with a VERY QUICK response from host. Great location in quiet neighborhood. I would stay here again in a heartbeat. "
Great 3 bedroom rental unit near Logan Square

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (66)
"Fit our whole family nicely."
Breathtaking home close to Schaumburg, Chicago

Des Plaines Vacation Rental w/ Spacious Backyard!

8.8 out of 10, Excellent, (15)
"Easy access good parking clean well stocked but very small three bedroom house with nice outdoor sitting and eating area near Rosemont"
Des Plaines Vacation Rental w/ Spacious Backyard!

Belmont House, Classy & Chic/walk to Wrigley Field

9.4 out of 10, Exceptional, (50)
"Great bang for your buck. Great area and great communication "
Belmont House, Classy & Chic/walk to Wrigley Field

Chic and Spacious Bi-level 3BD in Bucktown!

2.0 star property
10.0 out of 10, Exceptional, (7)
"Property was comfortable, clean, and in a great location."
Chic and Spacious Bi-level 3BD in Bucktown!

New home w/view & party deck - 2nd Floor

3.0 star property
10.0 out of 10, Exceptional, (23)
"Great location. Host was accessible and prompt to respond. "
New home w/view & party deck - 2nd Floor

Entire 3 Bedroom Cozy Unit

9.6 out of 10, Exceptional, (19)
"Just the right place for a quick trip with family! Great place if you are heading to Great Lakes for a Bootcamp graduation."
Entire 3 Bedroom Cozy Unit

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (61)
"Great spot."
The price is CA $149
CA $285 total
includes taxes & fees
Sep 2 - Sep 3
Master qtr close to nature & easy urban facilities

Lincoln Park Living - Suite 1

9.6 out of 10, Exceptional, (31)
"Ideal location and plenty of beds. Communication was easy. My friends and I kept saying how lucky we were to find this place. Highly recommend! "
Lincoln Park Living - Suite 1

Family frndly TwnHm by navy base

2.0 star property
9.6 out of 10, Exceptional, (19)
"Great little place to stay near the base. "
Family frndly TwnHm by navy base

Home w/ Fenced Yard: 13 Mi to Downtown Chicago!

6.4 out of 10, (5)
Home w/ Fenced Yard: 13 Mi to Downtown Chicago!

Home Sweet Home Spacious 4bed house with WiFi & Parking in fantastic Skokie

8.0 out of 10, Very good, (4)
"The house was in a nice neighborhood and was very roomy and comfortable. Will be back."
Home Sweet Home Spacious 4bed house with WiFi & Parking in fantastic Skokie

3-bedroom building in lovely Westchester with AC, WiFi. Enjoy your stay

8.0 out of 10, Very good, (2)
"Awesome place in a very good location (quiet neighborhood). The owner was very responsive with communication and the property was very clean & spacious! 10/10!"
3-bedroom building in lovely Westchester with AC, WiFi. Enjoy your stay
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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