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Compare 41 Condo Rentals in Highwood with updated reviews, rates, and availability.

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

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (196)
"Great property and easy process to check in/out. Lots of space and privacy. It was easy to get around and explore the city. "
Walking distance to restaurants, shops and Lake Michigan,

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

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

2.0 star property
10.0 out of 10, Exceptional, (7)
"The property was wonderful! It was clean and located perfectly for getting around the north shore. We enjoyed our visit!! "
"Melody of Evanston" 3BD, 2BA UrbanLux Condo

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

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

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

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,

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

10.0 out of 10, Exceptional, (101)
"Really enjoyed our stay. Parking was easy and we could walk to restaurants. Felt very safe and the neighborhood was welcoming. Would stay again."
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment

Pet-Friendly Urban Chicago Vacation Rental Condo

9.2 out of 10, Wonderful, (14)
"Great place to stay. Close to everything. Nice and clean "
Pet-Friendly Urban Chicago Vacation Rental Condo

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 AED 551
AED 942 total
includes taxes & fees
5 Mar - 6 Mar
Just remodeled apartment close to airport and mall

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

9.8 out of 10, Exceptional, (11)
"The property itself and the host, Mark, were some of the best I have experienced. The experience of booking a vrbo THROUGH expedia was a nightmare. Texts about communications came to me via expedia with link to access the message - but that lead to a dead link into vrbo that said I had no reservation. The chat within expedia to try and access check in information was impossible and would not lead to a live person. No info on a phone number to contact. Had to google and then get to several...
Parking, Balcony, Near Universities, Ravinia, NAPA & Train to Chicago

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 AED 591
AED 1,498 total
includes taxes & fees
5 Mar - 6 Mar
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking

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

10 min walk to Stevenson Convention Center

8.4 out of 10, Very Good, (5)
"Good "
10 min walk to Stevenson Convention Center

The Bright Retreat in Andersonville

9.8 out of 10, Exceptional, (54)
"This condo was a wonderful place to stay. The location is very close to the redline CTA, as well as to the quaint Andersonville, full of nice restaurants and bars. It felt safe, in a quiet neighborhood. We would definitely stay here again."
The Bright Retreat in Andersonville

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

10.0 out of 10, Exceptional, (21)
"It's a short walk to the yellow line L station and Dempster pulse station. We loved the delis close by- fresh bagels! The space itself was bright and airy and the listing accurate. "
Free Parking, Balcony, near Universities, NAPA, Ravinia and 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)
"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

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!

Studio- King Bed| HDTV| Airport| Safe Neighborhood

10.0 out of 10, Exceptional, (1)
Studio- King Bed| HDTV| Airport| Safe Neighborhood
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

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (24)
"The property listing was exactly as described. Very clean and quite spacious. We arrived at 530 pm and found adequate street parking. The beds were comfortable, the kitchen was stocked with key necessities and the bathrooms provided plenty of towels and basic toiletries. Our host was responsive with any concerns too. I would definitely recommend this property!"
Great 3 bedroom rental unit near Logan Square

Charming Wrigleyville Home Close to the Cubs!

9.4 out of 10, Exceptional, (16)
"Great walkable location with easy access to everything. We appreciated the parking passes so much. Brian has a very nice set up eith ever3you need for a great weekend getaway. "
Charming Wrigleyville Home Close to the Cubs!

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

9.4 out of 10, Exceptional, (44)
"Just as described and fit our needs perfectly. Super clean"
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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