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Compare 437 Vacation Homes in Highland Park with updated reviews, rates, and availability.

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!
Lincoln Park Living - Suite 2!
Living Room / Dining Room

Lincoln Park Living - Suite 2!

10.0 out of 10, Exceptional, (17)
"Very convenient. Spacious and comfortable condo."
Lincoln Park Living - Suite 2!
Great 3 bedroom rental unit near Logan Square
Interior

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (21)
"The property was perfect for me and my buddies for a football weekend!"
Great 3 bedroom rental unit near Logan Square
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Interior

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

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
New Humble Home! - Near Six Flags & Naval Base!!
Room

New Humble Home! - Near Six Flags & Naval Base!!

8.8 out of 10, Excellent, (22)
"The home is very close to base and was clean. The stairs to the second floor are old and not straight which can be a hazard. It worked for what we needed."
New Humble Home! - Near Six Flags & Naval Base!!
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design

Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design

7.4 out of 10, Good, (3)
"As good as advertised. Plenty of room for our group. Definitely recommend. "
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Charming, luxe, modern home near Naval base, Six flags, Casino, Gurnee Mills
Living area

Charming, luxe, modern home near Naval base, Six flags, Casino, Gurnee Mills

9.8 out of 10, Exceptional, (9)
"It was a quiet and cozy home near Great Lakes RTC. Great location. "
Charming, luxe, modern home near Naval base, Six flags, Casino, Gurnee Mills
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
Interior

Chicago Bootlegger House Sleeps 11-22 with 3 parking spots

10.0 out of 10, Exceptional, (32)
"We had a great time staying here for a family trip. Plenty of space for games, cooking, sleeping, talking. We only used a fraction of what was available. When we had trouble figuring out heating system, host was very responsive. "
Chicago Bootlegger House Sleeps 11-22 with 3 parking spots
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Room

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

9.2 out of 10, Wonderful, (15)
"Close to everything for My Son Graduation . We where less then 5 Miles from the Navy Station. I like that We had 6 Beds for everyone could sleep. The Kitchen was perfect for cooking meals. "
New Your Home Away From Home! - Near Great Lakes Naval Base!!
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
Living area

⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐

9.8 out of 10, Exceptional, (6)
"This is a very nice property. The only thing I caution is that it’s a 3rd floor walk up (actually on the 4th floor because there is nothing on the ground floor). "
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
Entire Beautiful Grove Home
Living area

Entire Beautiful Grove Home

10.0 out of 10, Exceptional, (5)
"The house was perfect. Family was content with location to base which allowed our soldier to spend more time with us and not have to worry about leaving us too soon to be back on base on time. "
Entire Beautiful Grove Home
Wicker Park Entire House, Private Yard and Parking!
Interior

Wicker Park Entire House, Private Yard and Parking!

10.0 out of 10, Exceptional, (7)
"Walking distance to the best pastries you will ever eat (Mindys) and the best Ramen you will ever eat (Oii Star). Walking distance to the best line (Blue Line). Place was great, location was great! "
Wicker Park Entire House, Private Yard and Parking!
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Living area

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

9.4 out of 10, Exceptional, (81)
"Overall a great place to stay. Location is really great. You can walk to all of Old Town. Well equipped property. As the only member of our group that drove, was nice to have a garage! "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Living room: 55” tv w/roku Air mattress Sectional Chase

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (20)
"The home is exactly as described…VERY comfortable beds and living room. Bed linens and towels are a great quality. Clean all around. I can tell great effort has been made to make our stay comfortable. Great location, as the home is just minutes away from the Great Lakes Navy Base where we attended Bootcamp Graduation for my daughter, as well as taking her back and forth from Base for her Liberty time. Close to shopping and dining.Only 35 minutes to O’Hare Airport, which was an easy commute. The...
The price is AED 588
AED 1,014 total
includes taxes & fees
7 Dec - 8 Dec
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
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
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Room

Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

9.6 out of 10, Exceptional, (79)
"This Old Town property was an excellent base for walking exploration of Lincoln Park (Saturday Farmer's Market was fantastic!) and Old Town itself (lively, with very good food, residential neighborhoods, shops, and entertainment), and had easy access to CTA trains to the Loop, Riverwalk, Millennium Park, and much more, had we had time. 7 adults (seniors) spent four nights, and found the four bedrooms, four bathrooms, large fully-equipped kitchen, and living/dining room/patio provided plenty of...
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Breathtaking home close to Schaumburg, Chicago
Exterior

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (43)
"Great house in a great locations. Beautiful backyard with ample room and swing set for the kids. The rooms are big with very comfortable beds. Love the house. "
Breathtaking home close to Schaumburg, Chicago
Chicago-burb -Medinah -1 King and 1 Queen beds
Living area

Chicago-burb -Medinah -1 King and 1 Queen beds

9.4 out of 10, Exceptional, (15)
"Nice and quiet neighborhood. Host was great! Highly recommended!!"
Chicago-burb -Medinah -1 King and 1 Queen beds
Great location-King beds-Kids playroom
Huge and beautiful family room with access to outdoor patio

Great location-King beds-Kids playroom

10.0 out of 10, Exceptional, (17)
"We did enjoy our stay in this beautiful home. We had everything we needed to be comfortable. The location was perfect fou our needs."
Great location-King beds-Kids playroom
"Charming 3-Bedroom Home
Bathroom

"Charming 3-Bedroom Home

10.0 out of 10, Exceptional, (2)
"Just beautiful!"
"Charming 3-Bedroom Home
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
Outdoor pool

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (269)
"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"
The price is AED 645
AED 830 total
includes taxes & fees
26 Nov - 27 Nov
Level Chicago – Old Town
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,
Wrigley/Southport Corridor Garden Oasis +parking!
Living area

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (66)
"This little apartment is close to my cousin in Wrigleyville and a perfect location to get downtown and to see a Bears game (they are terrible right now). Entry instructions were easy and apartment was very clean."
Wrigley/Southport Corridor Garden Oasis +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.