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Highwood Vacation Rentals

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Check prices for these dates

Tonight
Oct 29 - Oct 30
Tomorrow
Oct 30 - Oct 31
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Vacation Rentals in Highwood

Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher
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 ￥26,691
￥30,555 total
includes taxes & fees
Nov 11 - Nov 12
The Gem Museum Suites
Desk, iron/ironing board, WiFi, bed sheets
Relaxing Chicago Studio
Relaxing Chicago Studio
9.8 out of 10, Exceptional, (28)
"Had a great stay. Great location. "
United States
Justin
The price is ￥9,130
￥23,472 total
includes taxes & fees
Nov 4 - Nov 5
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, (42)
"Great studio apartment. Needed just one night and worth the price. Would recommend."
United States
Sahm
The price is ￥11,413
￥23,472 total
includes taxes & fees
Oct 30 - Oct 31
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 ￥11,413
￥27,777 total
includes taxes & fees
Nov 2 - Nov 3
Nice 1BR Spot, Unwind & Relax
1 bedroom, iron/ironing board, travel crib, WiFi
1BR Apartment in Chicago
1BR Apartment in Chicago
8.8 out of 10, Excellent, (9)
"Awesome "
United States
Robert
The price is ￥11,413
￥27,777 total
includes taxes & fees
Nov 2 - Nov 3
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
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)
"Great location and great host!"
United States
Brianna N.
Great 3 bedroom rental unit near Logan Square
1 bedroom, iron/ironing board, travel crib, 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 ￥11,413
￥27,777 total
includes taxes & fees
Nov 2 - Nov 3
Prime City Stay in a 1BR Apt
Exterior
2-bedroom apartment just 2 minutes drive to Wrigley Field
2-bedroom apartment just 2 minutes drive to Wrigley Field
2.0 star property
9.6 out of 10, Exceptional, (48)
"Great place to stay when you’re in town for the Cubbies! "
United States
Eric
The price is ￥24,515
￥55,786 total
includes taxes & fees
Nov 2 - Nov 3
2-bedroom apartment just 2 minutes drive to Wrigley Field
Exterior detail
Charming Wrigleyville Home Close to the Cubs!
Charming Wrigleyville Home Close to the Cubs!
9.4 out of 10, Exceptional, (38)
"Great stay"
United States
David B.
Charming Wrigleyville Home Close to the Cubs!
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)
"Location was close to airport, restaurants and shopping"
United States
Dorothy J.
The price is ￥20,543
￥38,581 total
includes taxes & fees
Oct 30 - Oct 31
Just remodeled apartment close to airport and mall
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)
"Very clean and really solid location. The host was on top of communication and made sure that everything went well for my stay."
United States
Isaak E.
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Fridge, microwave, oven, stovetop
Charming 3-bedroom house in Grayslake
Charming 3-bedroom house in Grayslake
10.0 out of 10, Exceptional, (22)
"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
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, (3)
"Barrington was an adorable town tucked away just an hour out of Chicago. This property is the perfect spot for a getaway with your loved one. My boyfriend and I had an amazing weekend and will definitely stop by again in the future!"
United States
Cierra F.
The price is ￥19,173
￥32,395 total
includes taxes & fees
Oct 30 - Oct 31
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Smart TV
Central Haven Escape: Stylish 3BR With Free Parking
Central Haven Escape: Stylish 3BR With Free Parking
6.8 out of 10, (6)
"Very nice place and nice host "
United States
Maryo K.
Central Haven Escape: Stylish 3BR With Free Parking
TV
Uptown Studio Gem Sum
Uptown Studio Gem Sum
7.2 out of 10, Good, (5)
"This studio is very clean and is located in a neighborhood with access to anything you would want to do or see. The stairway and halls are not pristine, but studio is good. Neighbors were quiet and seldom seen during my stay. Excellent restaurant right across the street and grocery nearby. Wrigley Field is easy walk. Check in was confusing for me, but it worked out. "
United States
Leah W.
The price is ￥12,478
￥27,502 total
includes taxes & fees
Nov 4 - Nov 5
Uptown Studio Gem Sum
Smart TV, books
Entire 3 Bedroom Cozy Unit
Entire 3 Bedroom Cozy Unit
9.4 out of 10, Exceptional, (23)
"This property was comfortable and convenient for our attendance at the Navy boot camp graduation. "
United States
Hallie G.
Entire 3 Bedroom Cozy Unit
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)
"Super comfy for families and the nicest host. "
United States
Anonymous traveler
The price is ￥51,494
￥81,624 total
includes taxes & fees
Oct 30 - Oct 31
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Fridge, microwave, oven, stovetop
Cozy & Furnished 2BR Unit
Cozy & Furnished 2BR Unit
9.4 out of 10, Exceptional, (12)
"This lovely 2 bedroom apartment was just perfect for our visit. It's just a few blocks to fun Lincoln Park which has lots of little shops & great restaurants. Best of all it was just a short walk to our daughter's place. The apartment was very clean and the beds were super comfortable. Any questions we had were answered quickly. Big screen TV in living room, well stocked kitchen and plenty of hot water for showers. Pretty sure we'll be back!"
United States
Susan
The price is ￥14,152
￥33,643 total
includes taxes & fees
Nov 2 - Nov 3
Cozy & Furnished 2BR Unit
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

Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

10/10 Excellent
"Great "
Terrance 2-night trip
Posted 1 day ago
Wyndham Garden Schaumburg Chicago Northwest

Find out more about Highwood

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Frequently asked questions

Are there vacation rentals in Highwood?

Yes, there are vacation rentals where you'll be just 12.7 mi (20.4 km) from Six Flags Great America, offering you a more remote option to escape the hustle and bustle. Highwood is known for its shopping and restaurants.

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

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families : This vacation home rental near Highwood offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Make the most of the selection of games in this rental home to help you unwind.

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 larger area, you’ll find Naval Base Great Lakes and Lake Forest College.

What are vacation rentals like in Highwood?

Vacation rentals are private properties you can reserve for a short or long stay in Highwood. Vacation rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips.