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Browse Select Highland Park Vacation Homes

Highland Park Family Ranch - Walk to Lake & Metra to Chicago!

Highland Park Family Ranch - Walk to Lake & Metra to Chicago!

Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

The price is CA $884
CA $1,568 total
includes taxes & fees
Sep 1 - Sep 2
Sunset Manor: Opulent Mansion, Ultimate Serenity Awaits

The One: A 1BR Stay That Feels Like Home

8.0 out of 10, Very good, (1)
"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."
The price is CA $143
CA $298 total
includes taxes & fees
Sep 2 - Sep 3
The One: A 1BR Stay That Feels Like Home

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 CA $173
CA $294 total
includes taxes & fees
Aug 31 - Sep 1
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

Cozy studio in Andersonville Chicago

9.2 out of 10, Wonderful, (24)
"It was a great location, internet was a little spotty on streaming services but we were in walking distance to so much it was worth it "
The price is CA $89
CA $195 total
includes taxes & fees
Sep 2 - Sep 3
Cozy studio in Andersonville Chicago

Prime City Stay in a 1BR Apt

9.2 out of 10, Wonderful, (9)
The price is CA $117
CA $267 total
includes taxes & fees
Sep 7 - Sep 8
Prime City Stay in a 1BR Apt

Homey 1BR Space Apartment

9.2 out of 10, Wonderful, (5)
"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 CA $117
CA $267 total
includes taxes & fees
Sep 9 - Sep 10
Homey 1BR Space Apartment

Peaceful 1BR Escape in Evanston

9.4 out of 10, Exceptional, (3)
"Quiet, clean and spacious! A peaceful neighborhood. "
The price is CA $121
CA $267 total
includes taxes & fees
Sep 3 - Sep 4
Peaceful 1BR Escape in Evanston

4BR Retreat w/ Theater, Game Room & Backyard

7.4 out of 10, Good, (9)
The price is CA $77
CA $681 total
includes taxes & fees
Sep 23 - Sep 24
4BR Retreat w/ Theater, Game Room & Backyard

Chic Studio in Heart of Chicago

10.0 out of 10, Exceptional, (1)
The price is CA $124
CA $275 total
includes taxes & fees
Sep 2 - Sep 3
Chic Studio in Heart of Chicago

Comfortable 2BR Chicago Apt

9.6 out of 10, Exceptional, (4)
"Perfect location for our trip. Very functional and comfortable. "
The price is CA $136
CA $310 total
includes taxes & fees
Sep 30 - Oct 1
Comfortable 2BR Chicago Apt

Tiny Home Retreat with hot tub

8.0 out of 10, Very good, (2)
"We had the most wonderful time"
The price is CA $177
CA $418 total
includes taxes & fees
Sep 1 - Sep 2
Tiny Home Retreat with hot tub

Great Layout – Spacious 2BR Apt

10.0 out of 10, Exceptional, (3)
"Clean, comfortable, and would definitely stay again!"
The price is CA $121
CA $292 total
includes taxes & fees
Sep 22 - Sep 23
Great Layout – Spacious 2BR Apt

2BR Traveler's Favorite, Modern and Clean

10.0 out of 10, Exceptional, (1)
"The place was really nice and clean, an excellent stay that ill consider again my next trip to chicago"
The price is CA $74
CA $492 total
includes taxes & fees
Sep 2 - Sep 3
2BR Traveler's Favorite, Modern and Clean

Near O’Hare/King Bed/Fenced yard/FirePit+Game room

9.8 out of 10, Exceptional, (31)
"Rented this spot because it was central to several family members living in surrounding cities. Had a great large backyard for the kids and nice deck for the adults. House was comfortable and and perfect for us."
The price is CA $285
CA $610 total
includes taxes & fees
Sep 1 - Sep 2
Near O’Hare/King Bed/Fenced yard/FirePit+Game room

Cozy & Furnished 2BR Unit

9.8 out of 10, Exceptional, (7)
The price is CA $121
CA $299 total
includes taxes & fees
Sep 3 - Sep 4
Cozy & Furnished 2BR Unit

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (61)
"Great spot."
The price is CA $147
CA $280 total
includes taxes & fees
Sep 2 - Sep 3
Master qtr close to nature & easy urban facilities

3BR Complete and Spacious Apt

9.6 out of 10, Exceptional, (4)
"Spacious and well appointed. Great location with plenty of eating/drinking options within walking distance. "
The price is CA $135
CA $331 total
includes taxes & fees
Sep 2 - Sep 3
3BR Complete and Spacious Apt

Beautifully Set Up 2BR Space

9.8 out of 10, Exceptional, (6)
"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 CA $129
CA $302 total
includes taxes & fees
Sep 1 - Sep 2
Beautifully Set Up 2BR Space

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (63)
"Great experience, lots of cooking materials "
The price is CA $186
CA $451 total
includes taxes & fees
Sep 2 - Sep 3
Quaint Bungalow, near Great Lakes Naval 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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Top Highland Park Hotel Reviews

Find out more about Highland Park

Find out more about Highland Park

Highland Park Vacation Homes information

Number of reviews
Accommodation
587 Vacation Homes
Lowest Price
CA $81
Highest Price
CA $350

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