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Compare Condo Rentals in Highwood with updated reviews, rates, and availability.

Pet-Friendly Urban Chicago Vacation Rental Condo

9.0 out of 10, Wonderful, (16)
"This apartment was so cute, quiet and a great stay for my family and I. The host was able to accommodate extra blankets and towels for us during our stay. As well with it being a pet friendly property our dog enjoyed his stay and a little bit of the city life. Dinner is walkable as well as access to the main transit system. This is definitely a good spot for a girls trip or even a single that wanted to different kind of stay in Chicago!"
Pet-Friendly Urban Chicago Vacation Rental Condo

Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover

10.0 out of 10, Exceptional, (22)
"We were visiting our nephew, who lives around the block from this rental, so we didn't spend a lot of time in the rental, but it was absolutely sparkling clean, well-appointed, and lovely. We will definitely book it again. "
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover

North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment

10.0 out of 10, Exceptional, (103)
"We absolutely loved staying at this property. We stayed with three children under the age of 5 and everything we could have thought of for our kids was there. My kids especially loved the sparkles in the tub and some of the toys in the apartment. The host did a great job of recommending places we could go and checking in to make sure we were doing okay. The location is great, within walking distance to the train and great parks. Would recommend this spot to anyone witb families looking to...
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment

Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

9.6 out of 10, Exceptional, (25)
"The place was super nice, very clean, and quiet. It was perfectly located for our needs. We were visiting my daughter and brand new granddaughter, and hope to make it our new home away from home when we visit."
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago

9.8 out of 10, Exceptional, (13)
"My family had a long visit to Chicago and this apartment was perfect! It looks just as it appears in pictures. Very comfortable! We hope to stay here again!"
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (175)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
Walking distance to restaurants, shops and Lake Michigan,

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (197)
"Everything was as described. Pretty entry was to “beautiful lady” of a building. The unit we were in was nicely refurbished. Modern but the old building charm maintained. We traveled light so the in suite laundry was great. Brand new fridge the day we got there. Amazing bedding & towels. "
Walking distance to restaurants, shops and Lake Michigan,

Bright 2BR Apt w/ Private Entrance & Laundry

2.0 star property
8.0 out of 10, Very Good, (2)
"Stayed 3 nights visiting my son. Good location, large apt., nicely decorated. I wish the tub/shower had a grab bar. The jacuzzi tub has a high profile and is difficult for older adults to step in and out. It was quiet inside--even the nearby train was hard to hear. I did trip several times on the drain cover right outside the entry door. Be careful!"
Bright 2BR Apt w/ Private Entrance & Laundry

Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago

10.0 out of 10, Exceptional, (22)
"Property was in a good area, less than 15 min to our destination. Plenty of restaurants and shopping nearby. Mark communication was veey good as well. "
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago

"Melody of Evanston" 3BD, 2BA UrbanLux Condo

2.0 star property
10.0 out of 10, Exceptional, (8)
"Great place"
"Melody of Evanston" 3BD, 2BA UrbanLux Condo

Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort

10.0 out of 10, Exceptional, (22)
"Clean and convenient! Great responsiveness from the host and was very accommodating. I would stay again! "
Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort

For up to 6 Spacious lovely Chicago-style 3-BDR condo. Safe & quiet neighborhood

8.6 out of 10, Excellent, (17)
"Beautiful-friendly place "
For up to 6 Spacious lovely Chicago-style 3-BDR condo. Safe & quiet neighborhood

Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover

10.0 out of 10, Exceptional, (28)
"It was clean and in a great neighborhood. Only had trouble finding parking but still was an amazing trip. Would definitely recommend."
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover

SuperHost Large Roommate style 2 Bedroom, 2 Bath, Patio, Sunroom, L Kitchen

9.4 out of 10, Exceptional, (3)
"For a busy Chicago weekend it was nice to find this place! Pablo was quick to communicate, he even got us a basket of St. Patrick's Day swag, it was so nice of him. Any questions we had he was extremely pleasant and helpful. The apartment was just the right size with great amenities. "
SuperHost Large Roommate style 2 Bedroom, 2 Bath, Patio, Sunroom, L Kitchen

The Bright Retreat in Andersonville

9.8 out of 10, Exceptional, (56)
"Location of unit in the Andersonville area was just perfect and having a dedicated parking spot was awesome for this area!Communicating with the owners was superb!"
The Bright Retreat in Andersonville

Free Parking, Private Terrace Up to 10%off on 30day stay

10.0 out of 10, Exceptional, (36)
"Offerall good property"
Free Parking, Private Terrace Up to 10%off on 30day stay

Soft Suede and Warm Bricks at a Stylish Rogers Park Home

9.4 out of 10, Exceptional, (29)
"Thoroughly enjoyed our stay in Rogers Park! Place was clean, well-stocked, and very comfortable. Host was in close communication. Off-street parking appreciated. Location across the street from grocery store and easy access to Chicago and Evanston. Highly recommend!"
Soft Suede and Warm Bricks at a Stylish Rogers Park Home

"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite

10.0 out of 10, Exceptional, (44)
"In for the weekend for the football game. Great location, super clean, well stocked and comfortable. "
"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite

Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover

9.0 out of 10, Wonderful, (10)
"The apartment needs a deep cleaning. It’s been awhile. Coffee mugs were filthy — took a huge amount of time/effort to clean them. Dishes and utensils were not clean - someone when through the steps putting them in the dw but they were dirty with dried-on food. Very thoughtful chargers and night background devices. Was noisy in the morning and night so great! Great location for groceries. Great coffee maker. So close to being great. "
Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover

Greenhouse Inn, Evanston Northwestern Loyola Chicago. Kid Friendly w/parking

10.0 out of 10, Exceptional, (5)
"Our stay in Evanston was awesome. Our unit was spacious, roomy, clean and had everything we needed. The location in Evanston was close to our event venue in Chicago plus near downtown Evanston as well. It was also great to walk to Lake Michigan and nearby restaurants. We greatly enjoyed our stay and would happily stay there again."
Greenhouse Inn, Evanston Northwestern Loyola Chicago. Kid Friendly w/parking
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 Highwood

Bright Garden Studio

9.0 out of 10, Wonderful, (20)
"clean & nice. "
The price is SAR 240
SAR 824 total
includes taxes & fees
7 Apr - 8 Apr
Bright Garden Studio

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (50)
"As advertised. Excellent in every respect. "
The price is SAR 409
SAR 732 total
includes taxes & fees
7 Apr - 8 Apr
Master qtr close to nature & easy urban facilities

Chic, Cozy home, by Blue Line Train Stop + Free parking

9.4 out of 10, Exceptional, (46)
"This property is very clean and very cozy. The location is great, except at night, I was able to hear the train and highway traffic. My husband wasn't bothered at all. We still liked it and suited our needs. The amenities were excellent. There's plenty of parking. "
Chic, Cozy home, by Blue Line Train Stop + Free parking
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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