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Compare 493 Vacation Homes in Highland Park with updated reviews, rates, and availability.

Lincoln Park Living - Suite 1
10.0 out of 10, Exceptional, (2)
"We enjoyed the location of this unit. The place was clean and the beds were comfortable. The space worked well for our group."
Lincoln Park Living - Suite 1
Beautiful, Remodeled Penthouse Unit in Old Town!
9.6 out of 10, Exceptional, (7)
"This property is huge for a city apartment. Our family of 5 (two parents, three kids) had plenty of space. The newly updated kitchen is very pretty. It is a short walk to many restaurants and Lincoln Park Zoo. The property manager was very responsive to my questions. We would definitely stay here again."
Beautiful, Remodeled Penthouse Unit in Old Town!
Luxury Downtown Penthouse with Private Rooftop!
10.0 out of 10, Exceptional, (4)
"Good host"
Luxury Downtown Penthouse with Private Rooftop!
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Chic 3bed 2bath Home with free parking close to United Center
10.0 out of 10, Exceptional, (5)
"Everything was clean and we had a great experience"
The price is AED 918
AED 1,584 total
includes taxes & fees
10 Jun - 11 Jun
Chic 3bed 2bath Home with free parking close to United Center
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Brownstone in Gold Coast - Downtown
9.8 out of 10, Exceptional, (8)
"The unit is in a great location and easy to get around. I didn't have a car with me, so I didn't have to worry about parking. It was clean and easy to communicate with the owner. The building itself is an older Chicago building, although the unit has been updated. I really enjoyed my stay!"
Brownstone in Gold Coast - Downtown
Breathtaking home close to Schaumburg, Chicago
9.8 out of 10, Exceptional, (38)
"Our family had a wonderful experience! Fantastic location - safe and quiet neighborhood (feels very tucked away, we saw deer in the backyard and took peaceful walk/run around the area), close enough to walk to a restaurants/7-11, and close to the highway to travel in to the city! Great communication from Michael, very responsive. Layout was great for 3 families with spacious rooms, private bathrooms, and open layout. Very pleased with our visit!"
Breathtaking home close to Schaumburg, Chicago
Lincoln Park Living - Suite 2!
10.0 out of 10, Exceptional, (4)
"Property was in a great area, close to many popular spots and was fitted to house multiple people! Would recommend and come again!"
Lincoln Park Living - Suite 2!
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is AED 657
AED 833 total
includes taxes & fees
17 Jun - 18 Jun
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Modern & Stylish West Town Loft with Pool Table (Pets Allowed)
9.8 out of 10, Exceptional, (8)
"We enjoyed our stay. We were out exploring the city for the whole weekend so we didn’t spend a lot of time actually on-site. But it was a convenient location to all the things we wanted to do. It was also great for a place to crash at the end of the days. This is a great place to operate out of especially for groups! I would recommend it."
Modern & Stylish West Town Loft with Pool Table (Pets Allowed)
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.6 out of 10, Exceptional, (8)
"The proximity to Great Lakes Recruitment Center, Sarge’s Meet & Greet, restaurants, etc. is perfect. We were in town for our son’s boot camp graduation and knew we wanted more room to hang out than a typical hotel room would offer. It was great to be able to relax, watch movies, just hang out with our sailor for the precious two days we had. This place has location, location, location if you’re coming in for boot camp graduation."
The price is AED 533
AED 966 total
includes taxes & fees
16 Jun - 17 Jun
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Your Next Vacation Home
10.0 out of 10, Exceptional, (11)
"Our stay was perfect for the few days we stayed for my niece's wedding. We enjoyed the house and its accommodations. Our host, Pervaiz was wonderful as well. I will definitely come back and refer my friends and family. Thank you, Jeanette!!"
The price is AED 753
AED 1,287 total
includes taxes & fees
10 Jun - 11 Jun
Your Next Vacation Home
Roxan Corner
9.0 out of 10, Wonderful, (18)
"This duplex was perfect for my three sons and myself. We stayed five days to attend one of my son’s Navy Graduation! House was very clean and modern. Had everything we needed, was a nice neighborhood, quiet neighbors? Close to everywhere we needed to go. Only suggestion would be to have the owners secure the rugs, they are very slippery. "
Roxan Corner
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
9.6 out of 10, Exceptional, (71)
"Perfect property to wind down after a long day at work. Had all the essentials. Host was very quick to respond to messages and inquiries."
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (71)
"The house and location was perfect for our group trip to Chicago. Ample rooms and beds for everyone, and host was extremely responsive throughout the process and our stay. Walking distance to a bunch of great restaurants and bars. Would definitely stay again!"
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
10.0 out of 10, Exceptional, (150)
"we had a great stay in Lincoln Park. The house worked well for a group of 8 women. The owner was very responsive."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence
9.6 out of 10, Exceptional, (151)
"Property was just as described, clean and plenty of space! Location was perfect if you’re thinking of going to a Cubs game! Target literally next door and plenty of restaurants in walking distance! Host was great and even checked in with us during our stay. Would return!"
The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence
Suite 1 on Southport 4 Queen Beds!
10.0 out of 10, Exceptional, (2)
"We stayed for a bachelorette party for 2 nights and it worked out very well, the location is great and lots of parking. Theres only 1 bathroom so I would suggest bringing extra mirrors if staying with a group of friends."
Suite 1 on Southport 4 Queen Beds!
Spacious and Sleek 4BD/2.5BA - Logan Square!
9.4 out of 10, Exceptional, (10)
"We really enjoyed our stay here."
Spacious and Sleek 4BD/2.5BA - Logan Square!
Schaumburg Pool House
9.8 out of 10, Exceptional, (6)
"Great place and neighborhood, lots of restaurants and mall close by. Place was clean and conveniently located. We enjoyed our stay!"
Schaumburg Pool House
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See all available properties in Highland Park
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.

Other property types in Highland Park

Modern Luxe home w/Gameroom and Electric Fireplace
8.4 out of 10, Very Good, (6)
"We really loved our stay at this house with group of our friends. This place was just perfect, newly renovated and exactly looked like it is in pictures. The house has everything needed from games in basement to the cozy beds to rest at night. Host was incredibly responsive and made us feel right at home. Recommended nearby places to explore and we had a great getaway overall. I would stay here again when in town. 10/10!!"
Modern Luxe home w/Gameroom and Electric Fireplace
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (211)
"Loved all the neighborhood dogs & farmers market"
The price is AED 1,091
AED 1,308 total
includes taxes & fees
16 Jun - 17 Jun
Level Chicago – Old Town
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (188)
"Very nice property "
The price is AED 331
AED 350 total
includes taxes & fees
9 Jun - 10 Jun
WoodSpring Suites Chicago Addison
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.

Recent reviews of Highland Park hotels
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