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Compare 564 Vacation Homes in Highland Park with updated reviews, rates, and availability.

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (27)
"The neighborhood was very cute, but parking was an issue. We also realized the second day that the windows in the front room were not locked, and one of them was open. The curtains had them covered so we didn’t think to check the first night in. Also, i think the vacant apartment upstairs was being actively shown, so when we were at the property, there were several different folks coming in and out. Overall, it was comfy for the two nights we stayed."
Great 3 bedroom rental unit near Logan Square

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

10.0 out of 10, Exceptional, (164)
"We stayed here for my sister’s bachelorette. Location was great and the space was huge, perfect for our big group."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Modern 3Bd Townhome Near Beach & Base

9.8 out of 10, Exceptional, (19)
"This property was exactly what we were needing! Cute house, very well maintained and the leasing agents were responsive to any concerns. "
Modern 3Bd Townhome Near Beach & Base

Cozy 3-bedroom house in family-oriented Melrose Park.

10.0 out of 10, Exceptional, (6)
"The house was perfect, the neighborhood was perfect, and the host was perfect. From the time we arrived until the time we left, she was very friendly and always made sure to ask if we needed anything. She also left us wine and cookies which was a nice treat. We will definitely be back."
Cozy 3-bedroom house in family-oriented Melrose Park.

Updated Forest Park 3 BR Bungalow

10.0 out of 10, Exceptional, (101)
"My friends and I had a wonderful stay at this property. It is very cute and conveniently located in a nice neighborhood (Oak Park/Forest Park areas) with easy access to 290 that takes you straight to the heart of downtown Chicago. The house had many amenities and you can tell the hosts are very considerate/thoughtful. Would highly recommend! "
Updated Forest Park 3 BR Bungalow

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.2 out of 10, Wonderful, (89)
"We traveled to Chicago for a 3 day visit - this house was in a quiet neighborhood and walking distance to several coffee shops and diners. The house fit our family well and was warm and cozy."
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Charming ModernRetro Home!

9.2 out of 10, Wonderful, (13)
"Brittany was absolutely amazing. Her home was gorgeous and cozy. Served our needs exact. We will be coming back! "
Charming ModernRetro Home!

3Bed/2Bath Wrigley home w/view & party deck 443 ft from Wrigley Field - 3rd Fl

3.0 star property
9.8 out of 10, Exceptional, (27)
"Can’t get a better location if you want to be near wrigley! Nicole was great to deal with and we loved it. Will be back."
3Bed/2Bath Wrigley home w/view & party deck 443 ft from Wrigley Field - 3rd Fl

2 King Bdrms and 1 Queen Bdrm! 20 minutes to O'Hare Airport! Parks and Shopping!

9.2 out of 10, Wonderful, (16)
"We had a great stay."
2 King Bdrms and 1 Queen Bdrm! 20 minutes to O'Hare Airport! Parks and Shopping!

BoHo House - A Chic, 1903 Chicago Workers Cottage

10.0 out of 10, Exceptional, (10)
"Well located, comfortable and stylish home. The backyard was great to let the dog out and would be a fabulous place to hang out in warmer weather. Perfectly clean throughout, and great host communication made for a wonderful stay."
BoHo House - A Chic, 1903 Chicago Workers Cottage

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (50)
"As advertised. Excellent in every respect. "
The price is SAR 409
SAR 732 total
includes taxes & fees
9 Apr - 10 Apr
Master qtr close to nature & easy urban facilities

Family frndly TwnHm by navy base

2.0 star property
9.4 out of 10, Exceptional, (10)
"Great little place to stay near the base. "
Family frndly TwnHm by navy base

Riverfront Libertyville Retreat w/ Outdoor Kitchen

9.0 out of 10, Wonderful, (24)
"The house was so cozy and Fun. Perfect space for our family gathering and less then 15 minutes form the Navy base. Our guest host Coco was so great and personable. "
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Spacious and Sleek 4BD/2.5BA - Logan Square!

9.2 out of 10, Wonderful, (17)
"The unit is spacious but we only found 3 bedrooms not 4 as advertised. However it had 4 queen beds in 3 bedrooms. The bathrooms and carpet were not as clean as I like to see. The towels were small & thin with no extras to be found. The kitchen is nice but had little stock. The owner communicated well before the booking. The neighborhood is just ok. We were rarely at the unit except to sleep and get ready as the 5 of us were in town for a family wedding so lots of family events to attend. "
Spacious and Sleek 4BD/2.5BA - Logan Square!

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

9.6 out of 10, Exceptional, (8)
"The house is located in a neighborhood that is easily walkable and has anything you need within walking distance. Metro is located within a few blocks of the house and makes getting around easy."
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

9.6 out of 10, Exceptional, (17)
"Home was in a quiet & friendly neighborhood with easy access to everything."
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

Luxury duplex home in Roscoe Village/Wrigley Field with Free Steet Parking

9.8 out of 10, Exceptional, (10)
"This was such a nice place in a great location. Really clean, comfortable, everything we needed. I would stay here again. Thank you!"
Luxury duplex home in Roscoe Village/Wrigley Field with Free Steet Parking

New Your Home Away From Home! - Near Great Lakes Naval Base!!

9.2 out of 10, Wonderful, (23)
"Is about 2 miles from great lakes for graduation. Layout is different. Sleeps 11 seats 5 or 6 in the living room, big table...half bath in kitchen...is cold in the winter...have to park in the back...walk around to front.can parknon the street but not overnight. The main bathroom with tyb sbower is high but has handrail. It snowed while we were there...owner shoveled sidewalk once. Overall it suit our need..its not high end but it was nice. Plenty of towels...no wash clothes...clean.."
New Your Home Away From Home! - Near Great Lakes Naval Base!!

Urban Farmhouse near O’Hare Airport

9.2 out of 10, Wonderful, (38)
"We loved having dedicated parking and the old farmhouse worked perfect for our group. We didn’t spend a lot of time at the house but it was easy to get to the sightseeing we wanted to do, the house was clean, check in and out were super easy, host was VERY easy to communicate with and provided great information very quickly! Everything was clean and we had all we needed and beds were comfortable. Really great for our group!"
Urban Farmhouse near O’Hare Airport
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 Highland Park

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (300)
"Spacious, clean rooms! Large windows make for a fabulous view!"
The price is SAR 641
SAR 836 total
includes taxes & fees
13 Apr - 14 Apr
Level Chicago – Old Town

Wrigleyville Suites

2.0 star property
9.4 out of 10, Exceptional, (3)
"Very good place at a very good price! Communication is the only need for improvement in my opinion. "
The price is SAR 540
SAR 822 total
includes taxes & fees
6 Apr - 7 Apr
Wrigleyville Suites

Bright Garden Studio

9.0 out of 10, Wonderful, (20)
"clean & nice. "
The price is SAR 240
SAR 823 total
includes taxes & fees
7 Apr - 8 Apr
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.