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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

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

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, (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,
Stunning open floor plan is perfect for entertaining and gatherings.

Walking distance to restaurants, shops and Lake Michigan,

9.8 out of 10, Exceptional, (195)
"Ross, the property manager, is very courteous and helpful. Property clean and well-appointed. Family group with 2 dogs. Took Uber rides into city to see museums and shows. Garage parking was nice. Very quiet neighborhood at night. Overall a nice, well-managed property that we highly recommend."
Walking distance to restaurants, shops and Lake Michigan,
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

9.6 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
"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, (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
Chair,Furniture,Home Decor,Indoors,Table

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
Home Decor,Furniture,Indoors,Living Room,Couch

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

9.2 out of 10, Wonderful, (9)
"The apartment needs a deep cleaning. Itā€™s been awhile. Coffee mugs were filthy ā€” 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
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
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, (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
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, (99)
"Excellent stay and nice neighborhood."
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
Pet-Friendly Urban Chicago Vacation Rental Condo
Chicago Vacation Rental | 2BR | 1BA | 900 Sq Ft | Stairs Required

Pet-Friendly Urban Chicago Vacation Rental Condo

9.4 out of 10, Exceptional, (13)
"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
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 AEDĀ 551
AEDĀ 942 total
includes taxes & fees
28 Feb - 1 Mar
Just remodeled apartment close to airport and mall
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, (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
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
10 min walk to Stevenson Convention Center
Living area

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
Living Area- Pullout Couch has a Queen Size Memory Foam Mattress

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
Privet cover terrace

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
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)
"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!
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, (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

Studio- King Bed| HDTV| Airport| Safe Neighborhood

Studio- King Bed| HDTV| Airport| Safe Neighborhood
Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!! Cozy!
Living area

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

9.8 out of 10, Exceptional, (226)
"We had an extended stay and the place was great. Clean, large, chef's kitchen and really responsive manager. Great location in the City."
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

3-bedroom house WiFi in lovely Waukegan Near Gurnee
Private kitchen

3-bedroom house WiFi in lovely Waukegan Near Gurnee

2.0 star property
4.4 out of 10, (13)
"Cute little house at all the necessities convenient to Naval base where we spent most of our time"
3-bedroom house WiFi in lovely Waukegan Near Gurnee
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
Private kitchen

Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field

10.0 out of 10, Exceptional, (168)
"Hosts were responsive to our needs. Perfect location for our stay"
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field
Bright Garden Studio
Interior

Bright Garden Studio

8.8 out of 10, Excellent, (16)
"We had a great stay in this Evanston lower level studio apartment while in town for our reunion and Homecoming weekend at Northwestern. The studio is clean, nicely decorated, good amenities, and conveniently located to both the NU campus and downtown Chicago. Having a dedicated parking spot was awesome too, as the off-street parking fills up quickly in the evening. My only recommendation would be replacing the really firm mattress with a softer one, or a memory foam topper. All in all we had...
The price is AEDĀ 209
AEDĀ 760 total
includes taxes & fees
2 Feb - 3 Feb
Bright Garden Studio
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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