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Compare 510 Vacation Homes in Winnetka with updated reviews, rates, and availability.

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

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

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (86)
"Location of house is great, communication with owner is great. The house "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Eddy House, Roscoe Village Hideaway

10.0 out of 10, Exceptional, (5)
"Great house . "
Eddy House, Roscoe Village Hideaway

New Your Home Away From Home! - Near Great Lakes Naval Base!!

9.4 out of 10, Exceptional, (20)
"This was my first booking with VRBO, we were in Chicago for my niece's Navy graduation. Sam, the host, was extremely communicative. I had sent him a question in the inbox and he called me within 3 minutes. The property is spacious, only 4 minutes from base and very close to a multitude of restaurants. Very clean, kitchen was not lacking in glasses / plates / accessories. We had a wonderful stay and I highly recommend Sam's house. Thank you again, Sam!!"
New Your Home Away From Home! - Near Great Lakes Naval Base!!

Your Next Vacation Home

9.8 out of 10, Exceptional, (30)
"Very clean, extremely nice home. "
The price is AED 624
AED 1,124 total
includes taxes & fees
16 Feb - 17 Feb
Your Next Vacation Home

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (48)
"This home was clean, comfortable, spacious and inviting. Michael met us to provide key and a review of all the home offered. Spacious pantry and kitchen had everything we needed for entertaining. The large dining table and comfy couches were perfect for enjoying the football game Everone complimented the home’s beauty and lovely backyard setting. Would highly recommend and we will be back. Thank you!"
Breathtaking home close to Schaumburg, Chicago

Entire house 1 city block from Wrigley Field.

9.8 out of 10, Exceptional, (19)
"Very comfortable home close to Wrigley and to restaurants, coffee shop and shopping."
Entire house 1 city block from Wrigley Field.

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (47)
"This place was amazing!! The bed was super comfortable and the jet tub was out of this world!! It was very clean and quiet. The host was very accomodating and had great communication. My husband and stayed overnight because he had an army function to attend. This was perfects! to attend. "
The price is AED 400
AED 713 total
includes taxes & fees
17 Feb - 18 Feb
Master qtr close to nature & easy urban facilities

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (116)
"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!"
Luxury Home Away From Your Home

3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY

10.0 out of 10, Exceptional, (73)
"This property is in a great location that is quiet and convenient. The property was extremely clean and had essentials for our stay. This property was a great option for our family to stay together and there was plenty of room for all 6 of us adults. Fantastic place. Most definitely would stay again!!!"
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

10.0 out of 10, Exceptional, (39)
"We stayed here in January to visit some family and enjoy the city. The location of this place is amazing. its right downtown , very walkable to everything. The parking is great, with the 2 car garage it was heaven for being in the city. The property is so nice. Its massive. upstairs and downstairs ; with room for so many people. We ended up only have four people ; and just loved it. The living room is so cozy, with the fireplace and sofas, the property was perfect. Matches all the...
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

9.6 out of 10, Exceptional, (7)
"Stayed here for a week while attending a festival and central downtown location was good. Having the garage was very helpful but suggest you have a small car as the garages are very shallow. Common area with kitchen and TV is very spacious for lounging"
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Roxan Corner

8.4 out of 10, Very Good, (31)
"We were very pleased with the location of the home. The property seemed to be well maintained and accomodating. The only downfall was that it seemed very pricey for the time of year"
Roxan Corner

Cheery 2+bedroom home with free parking on premises

9.8 out of 10, Exceptional, (33)
"Third time staying at this property. Great property and location. "
Cheery 2+bedroom home with free parking on premises

Riverfront Libertyville Retreat w/ Outdoor Kitchen

9.0 out of 10, Wonderful, (21)
"This property was perfect for several family members to stay & be comfortable, especially with having their own bathroom. It was very clean & spacious. It is a unique & awesome property. I was in touch with the host. She was delightful & quick to reply. The neighborhood is very nice. The location was perfect to get to the base & close to the cute town of Libertyville. I would definitely stay here again! "
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Family frndly TwnHm by navy base

2.0 star property
9.6 out of 10, Exceptional, (5)
"We stayed here when our daughter graduated from the Navy. House is as described and sticked/furnished with all you need or would expect. House was clean. Neighborhood seemed a little "sketchy" but we had zero issues or concerns while we were there. If you are coming for a Navy graduation location is good. Less than 10 mintues to base except on graduatiin morning. Traffic is horrendous but were still able to get from home and in our seats in less than 90 minutes. Would recommend and stay again"
Family frndly TwnHm by navy base

Berwyn Beauty

10.0 out of 10, Exceptional, (13)
"Amazing... location, price, amenities, etc."
Berwyn Beauty

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions

9.4 out of 10, Exceptional, (8)
"Excellent home, plenty of room, very clean."
4 Bedroom, 2 Full Bath. Centrally Located. Near O'Hare Airport and attractions
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, (678)
"Perfect location, huge beautiful rooms, felt like a local. The pool was a huge plus!"
The price is AED 403
AED 581 total
includes taxes & fees
16 Feb - 17 Feb
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (430)
"Very Spacious (Superior two-bedroom apt). Amazing views from the ninth floor. Had everything appliance we needed. Never even need to resupply from the community cabinets. The blinds are not private enough. If you have lights on inside, you can see through easily. The bathroom has a thicker set of blinds but poses the same problem. It's embarrassing to be seen across from other apartment buildings. Also there were some electrical issues in our bedroom/bathroom. The exhaust fan in the bathroom...
The price is AED 327
AED 383 total
includes taxes & fees
9 Mar - 10 Mar
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (253)
"It was wonderful!"
The price is AED 415
AED 487 total
includes taxes & fees
6 Mar - 7 Mar
Sonder Market Hall
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.