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Highwood Holiday Rentals

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Check prices for these dates

Tonight
5 Nov - 6 Nov
Tomorrow
6 Nov - 7 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

Holiday Rentals in Highwood

Private kitchen
The Gem Museum Suites
The Gem Museum Suites
3.5 star property
9.4 out of 10, Exceptional, (94)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is HK$1,344
HK$1,539 total
includes taxes & fees
23 Nov - 24 Nov
The Gem Museum Suites
Desk, iron/ironing board, WiFi, bed sheets
Relaxing Chicago Studio
Relaxing Chicago Studio
9.8 out of 10, Exceptional, (29)
"Everything was pristine and comfortable. I highly recommend this place. "
United States
Joyce
The price is HK$428
HK$1,151 total
includes taxes & fees
11 Nov - 12 Nov
Relaxing Chicago Studio
1 bedroom, iron/ironing board, free WiFi, bed sheets
Cozy studio in Andersonville Chicago
Cozy studio in Andersonville Chicago
9.4 out of 10, Exceptional, (45)
"Host was friendly and easy to get a hold of. Property was very nice and clean!"
United States
Rachel M.
The price is HK$544
HK$1,151 total
includes taxes & fees
11 Nov - 12 Nov
Cozy studio in Andersonville Chicago
TV
Nice 1BR Spot, Unwind & Relax
Nice 1BR Spot, Unwind & Relax
9.8 out of 10, Exceptional, (19)
"Great stay"
United States
Kayla K.
The price is HK$560
HK$1,392 total
includes taxes & fees
9 Nov - 10 Nov
Nice 1BR Spot, Unwind & Relax
1 bedroom, iron/ironing board, travel cot, WiFi
1BR Apartment in Chicago
1BR Apartment in Chicago
8.8 out of 10, Excellent, (11)
"Great place to stay while in Chicago for the weekend. Right by the L to get around. We had a blast and would stay here again. "
United States
Riley M.
The price is HK$544
HK$1,374 total
includes taxes & fees
2 Dec - 3 Dec
1BR Apartment in Chicago
Microwave, oven, stovetop, dishwasher
Luxurious 3 Bedroom Apartment in Chicago
Luxurious 3 Bedroom Apartment in Chicago
9.4 out of 10, Exceptional, (34)
"Great apartment! Had everything we needed, very easy check in and out. The only issue we had was finding parking on the street. "
United States
Lauren G.
Luxurious 3 Bedroom Apartment in Chicago
Interior
Chic, Cozy home, by Blue Line Train Stop + Free parking
Chic, Cozy home, by Blue Line Train Stop + Free parking
9.2 out of 10, Wonderful, (62)
"Nice, quiet neighborhood but finding parking was difficult. "
United States
Debra D.
Chic, Cozy home, by Blue Line Train Stop + Free parking
Pool
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
10.0 out of 10, Exceptional, (111)
"Loved staying at Jamie’s place. Wonderful neighborhood and well kept apartment. Jamie was friendly and very helpful. "
United States
Bud F.
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Fridge, microwave, oven, stovetop
Great 3 bedroom rental unit near Logan Square
Great 3 bedroom rental unit near Logan Square
9.6 out of 10, Exceptional, (66)
"We came for Thursday Lollapalooza and a Friday Cubs game. Easy check in at the apartment and we were very satisfied with all aspects of the place! "
United States
Mike L.
Great 3 bedroom rental unit near Logan Square
Smart TV
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
10.0 out of 10, Exceptional, (4)
"Nice little spot in the NW Suburbs. Great jumping off point for everything further North and points South."
United States
Thomas Z.
The price is HK$980
HK$1,663 total
includes taxes & fees
7 Nov - 8 Nov
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Exterior detail
Charming Wrigleyville Home Close to the Cubs!
Charming Wrigleyville Home Close to the Cubs!
9.4 out of 10, Exceptional, (41)
"Great stay"
United States
David B.
Charming Wrigleyville Home Close to the Cubs!
TV
Uptown Studio Gem Sum
Uptown Studio Gem Sum
7.2 out of 10, Good, (5)
"Check in was pretty easy, 3 codes total to get into the apt but after a few days we had the codes memorized and it wasn't overwhelming anymore.Room was a bit crammed for 2 adults and a dog but we made it work for our 5 day stay. I would recommend that hosts have (2) luggage holders instead of (1). The bed was very comfortable and pillows were so soft!Apt was in a great location and neighborhood. We loved the area so much we may book there again if we visit Chicago again.You do either have to pay...
United States
Estrella G.
The price is HK$490
HK$1,232 total
includes taxes & fees
2 Dec - 3 Dec
Uptown Studio Gem Sum
Smart TV, books
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
2.0 star property
10.0 out of 10, Exceptional, (2)
"My friendsoíøMolly & her husband Jeams were accommodating, kind, and responsive. They answered any and all questions I had before this day as well as while we were there. Each room came with an extra chair and a beautiful mirror that was perfect for outfit checks and selfies, and a TV. The beds were comfortable and there were extra pillows and towels ready for you to go whenever you need it. The TV was perfect for shows and movies and music. Everything is up to date, NEW, and simple to use. Even...
United States
Engelica S.
The price is HK$2,379
HK$3,859 total
includes taxes & fees
10 Nov - 11 Nov
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Paper towels
Just remodeled apartment close to airport and mall
Just remodeled apartment close to airport and mall
10.0 out of 10, Exceptional, (15)
"Ihor was very nice and the communication was good. He responded pretty quickly. The place was cute and clean. Neighborhood was good and pleasant. "
United States
Karyn E.
The price is HK$1,050
HK$1,971 total
includes taxes & fees
9 Nov - 10 Nov
Just remodeled apartment close to airport and mall
Private kitchen
Your Next Vacation Home
Your Next Vacation Home
9.6 out of 10, Exceptional, (54)
"The property was clean and well organized! I enjoyed our stay!"
United States
Don G.
The price is HK$1,166
HK$2,370 total
includes taxes & fees
10 Nov - 11 Nov
Your Next Vacation Home
1 bedroom, iron/ironing board, travel cot, WiFi
Prime City Stay in a 1BR Apt
Prime City Stay in a 1BR Apt
9.2 out of 10, Wonderful, (11)
"It was even better than we thought it would be!"
United States
Kelly W.
The price is HK$544
HK$1,374 total
includes taxes & fees
2 Dec - 3 Dec
Prime City Stay in a 1BR Apt
Fridge, microwave, oven, stovetop
Charming 3-bedroom house in Grayslake
Charming 3-bedroom house in Grayslake
10.0 out of 10, Exceptional, (23)
"We just stayed for the night but it was the perfect place for our family of 5."
United States
James B.
Charming 3-bedroom house in Grayslake
Smart TV
Serene 3-bedroom apartment in Chicago
Serene 3-bedroom apartment in Chicago
9.2 out of 10, Wonderful, (25)
"This is a lovely spot, conveniently located a few steps from Clark street. We had a great stay."
Canada
Jordana C.
Serene 3-bedroom apartment in Chicago
Interior
Pet-friendly Abode, 2 Mi to Dtwn Evanston!
Pet-friendly Abode, 2 Mi to Dtwn Evanston!
3.0 star property
Pet-friendly Abode, 2 Mi to Dtwn Evanston!
Exterior detail
Master qtr close to nature & easy urban facilities
Master qtr close to nature & easy urban facilities
9.8 out of 10, Exceptional, (71)
"Easy check in / out, and a beautiful property. Thank you for having us!"
United States
Adam D.
The price is HK$693
HK$1,435 total
includes taxes & fees
10 Nov - 11 Nov
Master qtr close to nature & easy urban facilities
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 Highwood Hotel Reviews

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

10/10 Excellent
"The breakfast was amazing"
Leesa 2-night trip
Posted 2 days ago
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Find out more about Highwood

Search for holiday rentals in Highwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Highwood using one of the methods below:

  • View our selection of featured holiday rentals in Highwood
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  • Enter your travel dates to view the best deals on holiday rentals in Highwood while they last

Look no further and take a look at our great range of rental properties in Highwood!

Frequently asked questions

Are there holiday rentals in Highwood?

Yes, we offer holiday rentals where you'll be just 12.7 mi (20.4 km) from Six Flags Great America, providing a more secluded option if you want peace and quiet. Highwood is known for its shopping and restaurants.

What are some of the best holiday rentals that Highwood has to offer?

Great 3 bedroom rental unit near Logan Square: This holiday home rental outside of Highwood is located on a lake, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What can I see and do in Highwood?

While exploring the area, visit family-friendly sights like Six Flags Great America, or get outside and enjoy nature at Chicago Botanic Garden. In the wider area, you’ll find Naval Base Great Lakes and Lake Forest College.

What are holiday rentals like in Highwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highwood. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a family trip.