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Compare 44 Condo Rentals in Highwood with updated reviews, rates, and availability.

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (194)
"The apartment is beautifully decorated and updated. Ross, the host gave us a welcome tour and everything was clearly explained. Beds are comfortable and rooms are spacious. We were relieved our rental minivan (just barely) fit in the garage! We did the kitchen wasn't as well equipped as we would have liked, but we were cooking a Thanksgiving meal which may have been a bit ambitious. The meal turned out well and we enjoyed our stay immensely!"
Walking distance to restaurants, shops and Lake Michigan,

Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

9.6 out of 10, Exceptional, (24)
"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

Bright 2BR Apt w/ Private Entrance & Laundry

2.0 star property
8.0 out of 10, Very Good, (1)
Bright 2BR Apt w/ Private Entrance & Laundry

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

10.0 out of 10, Exceptional, (99)
"Excellent stay and nice neighborhood."
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment

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

9.8 out of 10, Exceptional, (53)
"Great to have a parking space! Close to stores and restaurants. "
The Bright Retreat in Andersonville

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!

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

2.0 star property
10.0 out of 10, Exceptional, (6)
"The Melody was a fantastic apartment. Perfect location, the right size for our family, easy to get to and from campus. Our host a very quick to respond to any question. An added bonus was the parking spot looked inside the parking garage. "
"Melody of Evanston" 3BD, 2BA UrbanLux Condo

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (174)
"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,

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 1,010
SAR 2,025 total
includes taxes & fees
6 Jan - 7 January 2025
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking

Pet-Friendly Urban Chicago Vacation Rental Condo

9.4 out of 10, Exceptional, (13)
"Great place to stay. Close to everything. Nice and clean "
Pet-Friendly Urban Chicago Vacation Rental Condo

10 min walk to Stevenson Convention Center

8.6 out of 10, Excellent, (4)
"We had a comfortable stay for the most part. Location was clean and comfortable. It’s central to a lot of what Rosemont has to offer. That was awesome. Communication with host was lagging.. upon arrival the toilet lever inside the tank cracked in half- we were able to jimmy rig it, told the host with no response. Was not given check out Instructions so we just did what we would’ve wanted someone to do at our house. Throw garbage away outside, wash dishes etc. other than that…. A bang for our...
10 min walk to Stevenson Convention Center

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

10.0 out of 10, Exceptional, (21)
"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

10.0 out of 10, Exceptional, (31)
"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

9.8 out of 10, Exceptional, (8)
"Nice condo. Comfortable bed. Very clean Will definitely stay here again!"
The price is SAR 563
SAR 971 total
includes taxes & fees
3 Jan - 4 January 2025
Just remodeled apartment close to airport and mall

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

Urban Chicago Escape ~ 1 Mi to Local Beaches!

9.2 out of 10, Wonderful, (15)
"The place was clean and fit our needs. Great location near the lake and close to the train stop."
Urban Chicago Escape ~ 1 Mi to Local Beaches!

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

9.6 out of 10, Exceptional, (9)
"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

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

Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!! Cozy!

9.8 out of 10, Exceptional, (225)
"Thank you, Andrea, for your beautiful place. We stayed a month, and it was an ideal accommodation for a trip we'd planned for years. The condo is clean, comfortable and spacious — an open kitchen/dining/living room. It had all the conveniences we needed, and given how long we stayed, we made good use of the kitchen, washer/dryer and other amenities. Loved the location—a 15-minute walk in one direction to Wrigley Field and a 20-minute walk the other direction to Montrose Beach. (Tip: For better...
Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!! Cozy!
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

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

9.4 out of 10, Exceptional, (38)
"I'd stay again, it was nice. Only issue was the upstairs neighbor must have been doing remodeling because the entire day was filled with hammers, drills, stomping etc. But all in all I enjoyed it."
Chic, Cozy home, by Blue Line Train Stop + Free parking

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

10.0 out of 10, Exceptional, (120)
"We had an amazing time, and this home was a large part of why we enjoyed Chicago so much! The hosts were great, and very responsive to all of our questions! The home was spacious and warm. The perfect location, so close to the train so we could travel back and forth to downtown. The kitchen has a great space for cooking, what a great stove. The ping pong/billiards table was a hit! We would definitely stay here again! "
Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (174)
"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,
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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