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

Bright 2BR Apt w/ Private Entrance & Laundry
Chair,Furniture,Home Decor,Indoors,Table

Bright 2BR Apt w/ Private Entrance & Laundry

2.0 star property
Bright 2BR Apt w/ Private Entrance & Laundry
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)
"What a great place! Perfect for a stay close enough to everything! Very comfy beds, and couch (tv remote was literally the only thing I can complain about!)"
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
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

9.4 out of 10, Exceptional, (8)
"The property was nice and clean! Kitchen was well stocked minus cooking oil. Parking directions was a little confusing as it said the lot was marked Tony's Fresh Market Receiving, but it wasn’t and the parking space didn’t have visible numbers, esp at night. "
Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover
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,
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, (11)
"Host was very communicative. There is no parking even though the listing states parking. However street parking was fairly easy to find before 10pm. Would still stay again!"
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
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, (20)
"Had a great trip and this place was clean and quiet with plenty of room. Second sleeping area would make a great area to hang out and read for a while with the beautiful windows and natural light. "
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
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
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)
"I enjoyed my stay here very much. A comfortable, spacious and nicely appointed unit that also was very clean. The only challenges were with parking and finding the keys. Not much can be done about the former, and the latter was resolved fairly quickly. Thanks! "
Urban Chicago Escape ~ 1 Mi to Local Beaches!
"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
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, (173)
"Good location clean"
Walking distance to restaurants, shops and Lake Michigan,
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 706
SAR 1,669 total
includes taxes & fees
2 Dec - 3 Dec
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, (98)
"Great location, easy to get to from the L and bus, walking distance to shops and restaurants. Hosts were quick to communicate and checked to see if we needed anything. As described in the listing, you can hear a family above but only occasionally. Overall a great base for exploring Chicago!"
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
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, (20)
"Super clean, Host provided detailed information. Great location. Appreciate the off street parking. Very good experience. Host is doing a great job."
Free Parking, Balcony, near Universities, NAPA, Ravinia and train to Chicago
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
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 563
SAR 960 total
includes taxes & fees
30 Nov - 1 Dec
Just remodeled apartment close to airport and mall
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
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!
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
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover
Our living room has bright bay windows overlooking the street, and a beautiful (decorative!) fireplace - it's an ideal place to sit and read, or converse

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)
"Wonderful property conveniently located near the shore and the L. Only a few short stops away from Wrigley Field and an easy trip downtown. If you want to stay in Edwater there are plenty of great spots to eat and drink near by."
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! 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 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
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!
First floor living room with leather couch, smart cable TV, and Alexa speaker.

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

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

9.6 out of 10, Exceptional, (35)
"Very nice apartment. Could use more pillows (or fluffier). Just as advertised. "
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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