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Compare 475 Vacation Homes in Highland Park with updated reviews, rates, and availability.

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

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

9.6 out of 10, Exceptional, (16)
"Perfect location to make training visits to the area. Close to places to eat & grocery stores."
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

2 Mi to Northwestern: Updated Home w/ Game Room!

10.0 out of 10, Exceptional, (1)
2 Mi to Northwestern: Updated Home w/ Game Room!

Beautiful 5 bedroom home on private lake

Beautiful 5 bedroom home on private lake

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

9.4 out of 10, Exceptional, (87)
"Spacious property. Plenty of room and great neighborhood. Wish the larger TV was upstairs. "
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, (163)
"Great location, lots of space for gathering and hanging out. Tons of sleeping areas, air mattresses couches, futons, etc. Great for large groups of adults. Caution: Lots of stairs."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

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

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

10.0 out of 10, Exceptional, (4)
"This is a great place and very pet friendly. Only negatives were lack of hashtags (only one in the home), no hair dryer when it advertised it had one, and no TV in any of the bedrooms. The home was clean, spacious, fireplace and hot tub are a great bonus."
Cozy 3-bedroom house in family-oriented Melrose Park.

Your Next Vacation Home

9.6 out of 10, Exceptional, (33)
"The house and the area of town worked out very well for my family. I would stay there again. "
Your Next Vacation Home

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

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

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!

GORGEOUS 4/2.5 GREYSTONE HOME | WRIGLEY

8.4 out of 10, Very Good, (26)
"We booked this location for our large family of 8. Clean and it slept all of us well, with plenty of space to wind down and hang out after a day seeing the sights in the city. Easy walking distance to Wrigley field and local attractions. Short drive into the city or hop on the train a block away. Seemed like a safe neighborhood and has a garage for parking. (Note a Suburban is too long to park inside and still close the door)Good communication with property owner/management. We will...
GORGEOUS 4/2.5 GREYSTONE HOME | WRIGLEY

Stunning / Spacious 6BD Home + garage - Bucktown!

9.2 out of 10, Wonderful, (30)
"Location is great, size of the house is great with queen beds in all room and even one with a King bed. Basement was very cold, ( it’s winter) so that bedroom was not used but wasn’t needed anyways. The house needs a really good cleaning especially the kitchen especially the cabinets. Also coffee maker is tiny, doesn’t make sense considering the size of the house. Ironing board had no cover just metal frame, kitchen was not stocked properly for the size of the house. Loved the fact there was...
Stunning / Spacious 6BD Home + garage - Bucktown!

Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+

8.8 out of 10, Excellent, (8)
"The house was very nice. Great neighborhood."
Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+

The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!

9.8 out of 10, Exceptional, (73)
"We spent a wonderful long weekend enjoying the surrounding area. Plenty of shops, bars and restaurants within easy walking distance. The host was very good with communicating, unit was very spacious and clean. Perfect place to stay in Wrigleyville"
The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (57)
"We drove up from Florida for our son’s Navy graduation. After 2 days on the road, the second day mostly in the freezing ice & snow, it was wonderful to come into this cozy, warm home. I loved the details & character of this older home. The floors squeak a little & there’s some clanging as the heater turns on, but I loved those little bits. It made it feel so much more like a home rather than a hotel. The location was perfect for travel to & from Naval Station Great Lakes. There are plenty of...
The price is AED 496
AED 1,139 total
includes taxes & fees
15 Mar - 16 Mar
Quaint Bungalow, near Great Lakes Naval Base

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!!

Updated Forest Park 3 BR Bungalow

10.0 out of 10, Exceptional, (98)
"This Forest Park bungalow was perfect for our ladies weekend. It is clean, comfortable, updated, charming, well stocked with supplies, has off-street parking, and is convenient to the city. I highly recommend this lovely home."
Updated Forest Park 3 BR Bungalow

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

9.8 out of 10, Exceptional, (83)
"We had a wonderful visit in Chicago and this VRBO was a great place to stay for our group. There are plenty of bedrooms and bathrooms and it is close to all the restaurants, bars, and an El stop. "
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

Family frndly TwnHm by navy base

2.0 star property
9.8 out of 10, Exceptional, (6)
"We stayed here when our daughter graduated from the Navy. House is as described and sticked/furnished with all you need or would expect. House was clean. Neighborhood seemed a little "sketchy" but we had zero issues or concerns while we were there. If you are coming for a Navy graduation location is good. Less than 10 mintues to base except on graduatiin morning. Traffic is horrendous but were still able to get from home and in our seats in less than 90 minutes. Would recommend and stay again"
Family frndly TwnHm by navy base
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, (290)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is AED 596
AED 781 total
includes taxes & fees
13 Mar - 14 Mar
Level Chicago – Old Town

Wrigleyville Suites

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is AED 284
AED 517 total
includes taxes & fees
11 Mar - 12 Mar
Wrigleyville Suites

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!

9.2 out of 10, Wonderful, (73)
"Loved this location near Wrigley Stadium. "
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-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.