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Holiday Homes in Highland Park

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Featured Holiday Homes in Highland Park

Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

The One: A 1BR Stay That Feels Like Home

9.0 out of 10, Wonderful, (2)
"Very nice condo in a quiet neighborhood"
The price is AU$310
includes taxes & fees
27 Oct - 28 Oct
The One: A 1BR Stay That Feels Like Home

Prime City Stay in a 1BR Apt

9.2 out of 10, Wonderful, (10)
"Location is very good, 10 mins walk to irving blue line station, and the apartment has lot of light during the day as it was a corner unit."
The price is AU$276
includes taxes & fees
5 Oct - 6 Oct
Prime City Stay in a 1BR Apt

Relaxing Chicago Studio

10.0 out of 10, Exceptional, (17)
"Had a great stay. Great location. "
The price is AU$293
includes taxes & fees
21 Oct - 22 Oct
Relaxing Chicago Studio

Chic Vintage Studio in the Gold Coast

The price is AU$358
includes taxes & fees
7 Oct - 8 Oct
Chic Vintage Studio in the Gold Coast

Cozy & Furnished 2BR Unit

9.6 out of 10, Exceptional, (8)
The price is AU$326
includes taxes & fees
28 Oct - 29 Oct
Cozy & Furnished 2BR Unit

A quiet stay while you are away

9.8 out of 10, Exceptional, (32)
"We stayed a few nights and everything was nice and clean. Thank you!"
The price is AU$295
includes taxes & fees
7 Oct - 8 Oct
A quiet stay while you are away

2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill

9.0 out of 10, Wonderful, (2)
"The house was amazing. The beds were so comfortable. The stay was so fun. Thank you for everything!"
The price is AU$589
includes taxes & fees
5 Oct - 6 Oct
2BR • Sleeps 7 • Coffee Station • Backyard w/ Grill

Chic Studio in Heart of Chicago

10.0 out of 10, Exceptional, (2)
"Older property. Landlord special in the bathroom. Definitely needs better window coverings. Otherwise, comfortable, safe, and clean. "
The price is AU$294
includes taxes & fees
5 Oct - 6 Oct
Chic Studio in Heart of Chicago

Peaceful 1BR Escape in Evanston

8.0 out of 10, Very good, (5)
"Quiet, clean and spacious! A peaceful neighborhood. "
The price is AU$292
includes taxes & fees
7 Oct - 8 Oct
Peaceful 1BR Escape in Evanston

Homey 1BR Space Apartment

9.4 out of 10, Exceptional, (6)
"This was a wonderful base for the days I spent exploring Chicago. The apartment is clean and comfy and it is located right on the 'L' Brown line in a charming and vibrant neighborhood. I could zip to anywhere in the city I wanted on the L and felt very relaxed coming "home" each night."
The price is AU$280
includes taxes & fees
15 Oct - 16 Oct
Homey 1BR Space Apartment

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

10.0 out of 10, Exceptional, (1)
"Our experience at this place was unique; the best relaxing get away I have had in many years. From check-in to total comfort and cleanliness to privacy and coziness. And “Friends-Themed”accents made our stay specially touching. It was a delight walking downtown to great restaurants and stores while admiring beautifully maintained new and old architectural gems that made us feel both amazed and nostalgic. And more than anything, a town we felt safe and welcomed everywhere. It is for sure one of...
The price is AU$320
includes taxes & fees
4 Oct - 5 Oct
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

Theater • Game Room • Gym • Firepit • 4BR Home

7.6 out of 10, Good, (10)
"Comfy beds and a great house for kids and adults."
The price is AU$783
includes taxes & fees
28 Oct - 29 Oct
Theater • Game Room • Gym • Firepit • 4BR Home

Bright & Modern Lakeview Studio

9.6 out of 10, Exceptional, (8)
"This is a great location to hit the Lakeview neighborhood with Wrigley Field just a couple blocks over. When trying to get the check-in instructions, there were a lot of hoops to jump through to get the payment to the management company for this property. I had to contact the host (management company) multiple times to get the links to the forms to upload a driver's license and selfie holding said driver's license. Another URL to get to the payment Venmo account. And another URL for the...
The price is AU$293
includes taxes & fees
3 Nov - 4 Nov
Bright & Modern Lakeview Studio

Beautifully Set Up 2BR Space

9.8 out of 10, Exceptional, (9)
"Great apartment, plenty of room for 4 after a Cubs game, right by Wrigley. Would definitely stay here again for a ballgame."
The price is AU$328
includes taxes & fees
15 Oct - 16 Oct
Beautifully Set Up 2BR Space

Chic apartment with fitness room and AC in beautiful Chicago

6.8 out of 10, (3)
"Didn’t receive check in information until after book in time. This was after repeated messages, calls to property manager & VRBO. The actual apartment was tidy, however the drain in the tub was clogged. Parking was difficult and when asked if we could park in the lot behind the apartment, we were told it was 20 more a day. Was allowed to park there the second night at no cost. Communication once we were actually checked in was good. It’s in a lovely neighborhood and close to the train and...
The price is AU$392
includes taxes & fees
21 Oct - 22 Oct
Chic apartment with fitness room and AC in beautiful Chicago

Tiny Home Retreat with hot tub

8.8 out of 10, Excellent, (3)
"NICE PLACE, NICE NEIGHBORHOOD"
The price is AU$504
includes taxes & fees
6 Oct - 7 Oct
Tiny Home Retreat with hot tub

1-Bedroom Pad | Cozy + All-Set

10.0 out of 10, Exceptional, (1)
"This was a great space. The location was perfect and we had everthing we needed. We would definitely stay here again. "
The price is AU$293
includes taxes & fees
6 Oct - 7 Oct
1-Bedroom Pad | Cozy + All-Set

1BR Chic & Sunny Place

9.4 out of 10, Exceptional, (3)
"Location was perfect for visiting family and getting around the city. Bed was extra comfy and the AC worked wonderfully. Will stay here again on our next visit. "
The price is AU$276
includes taxes & fees
6 Oct - 7 Oct
1BR Chic & Sunny Place
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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Top Highland Park Hotel Reviews

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