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Compare 43 Condo Rentals in Highwood with updated reviews, rates, and availability.

"Melody of Evanston" 3BD, 2BA UrbanLux Condo
Living area
"Melody of Evanston" 3BD, 2BA UrbanLux Condo
2.0 star property
10.0 out of 10, Exceptional, (4)
"Our family gathered at this cute little place for a Chicago weekend. The condo was spacious for our family of eight (five adults and three kids), very quiet, and clean. Communication was excellent and accommodating. We’d highly recommend this property. "
"Melody of Evanston" 3BD, 2BA UrbanLux Condo
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago
Privet cover terrace
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago
10.0 out of 10, Exceptional, (19)
"Awesome stay!"
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago
Walking distance to restaurants, shops and Lake Michigan,
Large kitchen with open floor plan, hardwood floor throughout.
Walking distance to restaurants, shops and Lake Michigan,
9.6 out of 10, Exceptional, (171)
"Very easy to find. The host was friendly and was easy to communicate with. The condo was clean and and felt very safe. "
Walking distance to restaurants, shops and Lake Michigan,
Walking distance to restaurants, shops and Lake Michigan,
Stunning open floor plan is perfect for entertaining and gatherings.
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (193)
"Stayed two nights. Great location in Rogers park. Property manager is on site and gave a lovely tour of property. Also had a binder with restaurants, things to do, etc which I appreciate! Large kitchen, laundry, garage parking for car. Everything was lovely! "
Walking distance to restaurants, shops and Lake Michigan,
Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover
Home Decor,Furniture,Indoors,Living Room,Couch
Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover
9.6 out of 10, Exceptional, (7)
"This location is perfect for exploring the north side of Chicago. From Montrose Beach to Andersonville to Lincoln Square, it is ideal. I highly recommend this property for your next Chicago getaway. Paul B"
Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover
Brand new luxury space + roof deck in enchanting Chicago, with hi-speed WiFi.
Living area
Brand new luxury space + roof deck in enchanting Chicago, with hi-speed WiFi.
2.5 star property
10.0 out of 10, Exceptional, (1)
"The condo is very new and clean. Upscale appliances and finishes. The rooftop deck is very private and is equipped with comfortable furniture. We enjoyed hanging out there in the evenings. Chux is very quick to respond to questions. There are a lot of stairs going up to the condo. It is not suitable for people with mobility issues. "
Brand new luxury space + roof deck in enchanting Chicago, with hi-speed WiFi.
Pet-Friendly Urban Chicago Vacation Rental Condo
Chicago Vacation Rental | 2BR | 1BA | 900 Sq Ft | Stairs Required
Pet-Friendly Urban Chicago Vacation Rental Condo
9.2 out of 10, Wonderful, (10)
"A very clean and nice property. Plenty of activities nearby (food, coffee) and not a long drive from the city. My only very minor critique is that there wasn't any laundry detergent with the washer and dryer."
Pet-Friendly Urban Chicago Vacation Rental Condo
10 min walk to Stevenson Convention Center
Living area
10 min walk to Stevenson Convention Center
8.8 out of 10, Excellent, (3)
"The property was not the same as the pictures- I think it was probably another unit in the same building because the decor matched, but there were some definite differences. Aside from that, overall the stay was nice. The condo was very cozy, and it was incredibly close to everything we wanted to do. The shared yard space in the back was nice. The condo is also located close to the airport which is convenient for anyone traveling that way. "
10 min walk to Stevenson Convention Center
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Home Decor,Furniture,Indoors,Living Room,Table
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
9.8 out of 10, Exceptional, (22)
"This was an excellent property. We thoroughly enjoyed the lovely apartment accommodations. The Andersonville area is just a few blocks away and includes restaurants, artisan shopping, and walkability. Also it was close to some of the Broadway Ave theaters where we saw a show. It was easy to take a train back toward the city. Our daughter lives up north that way and We definitely would stay there again. "
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Just remodeled apartment close to airport and mall
Living area
Just remodeled apartment close to airport and mall
9.8 out of 10, Exceptional, (8)
"Nice condo. Comfortable bed. Very clean Will definitely stay here again!"
The price is SAR 564
SAR 975 total
includes taxes & fees
17 Nov - 18 Nov
Just remodeled apartment close to airport and mall
Urban Chicago Escape ~ 1 Mi to Local Beaches!
Chicago Vacation Rental | 2BR | 1BA | 1,100 Sq Ft | Stairs Required for Access
Urban Chicago Escape ~ 1 Mi to Local Beaches!
9.2 out of 10, Wonderful, (13)
"Our stay in Chicago was amazing and so relaxing! The apartment was clean, well stocked, and so close to the L that it makes travel into the city a breeze! The neighbourhood is safe, friendly, close to the lake, and there was never a problem finding a parking spot for our car. We can't wait to come back and stay here."
Urban Chicago Escape ~ 1 Mi to Local Beaches!
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago
Private kitchen
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago
9.6 out of 10, Exceptional, (8)
"The place was clean and spacious. I appreciated the parking space which made unloading the car to the apartment super easy. Communication from the host was helpful and check-in was a breeze. Would stay here again! "
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago
Free Parking, Balcony near Universities, NAPA, Ravinia and train to Chicago
All New 2022 Queen size bed Workstation Fast WiFi LED light Large closet
Free Parking, Balcony near Universities, NAPA, Ravinia and train to Chicago
10.0 out of 10, Exceptional, (7)
"I absolutely loved my stay - the property is SO clean, private, and peaceful! The kitchen has a large window where I had the perfect view of autumn leaves. The balcony is super cute! Easy walking distance to Target and the train station. Very easy check in and out. The owner was very responsive and kind. "
Free Parking, Balcony near Universities, NAPA, Ravinia and train to Chicago
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Interior
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
9.4 out of 10, Exceptional, (22)
"We could not have asked for a better host & the place was awesome. Thank you"
The price is SAR 470
SAR 1,382 total
includes taxes & fees
18 Nov - 19 Nov
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
View from the dining room into the living room. The sofa pulls out into a bed.
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
10.0 out of 10, Exceptional, (97)
"My husband and I were I town for a Cubs game and wanted to stay within walking distance of Wrigley. This was the perfect spot. The property feels spacious and we appreciated the extra touches like umbrellas and the white noise machines. I can’t say enough about the neighborhood. So many restaurants and shops within easy walking distance and great access to the Brown Line at Irving Park. The owners were easy to communicate with and quick to respond to questions. People highly sensitive to noise...
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
Soft Leather and Warm Bricks at a Stylish Rogers Park Home
Living area
Soft Leather and Warm Bricks at a Stylish Rogers Park Home
10.0 out of 10, Exceptional, (30)
"My family and I had a great stay at The Clark. This is a great, clean and cozy apartment with bonus amenities. Quality matresses, appliances, bluetooth speakers, and kitchenware. Master shower was clean, with plenty of towels. The kitchen and the beautiful wood countertop island served as a great area to congregate with my family. The check in was smooth, as our host, Lilian, provided access information prior to our arrival. She also made sure to check in with us during our stay to see how we...
Soft Leather and Warm Bricks at a Stylish Rogers Park Home
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
Furniture,Indoors,Living Room,Home Decor,Couch
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
10.0 out of 10, Exceptional, (19)
"we stayed for 2 nights. accomations were very clean and comfortable "
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
Soft Suede and Warm Bricks at a Stylish Rogers Park Home
Interior
Soft Suede and Warm Bricks at a Stylish Rogers Park Home
9.4 out of 10, Exceptional, (28)
"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
The Bright Retreat in Andersonville
Living Area- Pullout Couch has a Queen Size Memory Foam Mattress
The Bright Retreat in Andersonville
9.8 out of 10, Exceptional, (52)
"Great location. Nice neighborhood. Many things within walking distance. Great host. Host very responsive. "
The Bright Retreat in Andersonville
Wrigley 2 bedroom 2 bath with free parking & yard!
Lobby
Wrigley 2 bedroom 2 bath with free parking & yard!
10.0 out of 10, Exceptional, (3)
"Great location and ease of getting around. Great amenities."
Wrigley 2 bedroom 2 bath with free parking & yard!
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

Roxan Corner
Room
Roxan Corner
8.4 out of 10, Very Good, (28)
"Just what I needed. The property was clean and the neighborhood is quiet. I would definitely stay again."
Roxan Corner
Walking distance to restaurants, shops and Lake Michigan,
Large kitchen with open floor plan, hardwood floor throughout.
Walking distance to restaurants, shops and Lake Michigan,
9.6 out of 10, Exceptional, (171)
"Very easy to find. The host was friendly and was easy to communicate with. The condo was clean and and felt very safe. "
Walking distance to restaurants, shops and Lake Michigan,
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
Terrace/patio
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
10.0 out of 10, Exceptional, (34)
"Very clean and well thought out/supplied apartment on a lovely street a 30 second walk to Lake Michigan. There are 2 bedrooms, one larger master with en suite bathroom, and a second full bathroom and smaller bedroom. The unit is on the bottom floor so windows are high. Diane is friendly and responsive. The walk along the beach & out to an old lighthouse was a bonus. The street has mature trees and people walking dogs. There is a 7-11 on the corner and several restaurants walking distance. ...
The Holiday Lake House - 2br 2bth - 50 steps from the beach!
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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