Highwood Vacation Rentals

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Our top choices for Highwood vacation rentals

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
Barrington
9.8 out of 10, Exceptional, (8 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is CA $131
CA $235 total
includes taxes & fees
Apr 17 - Apr 18
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (34 reviews)
"This was a great apartment in the heart of Lincoln Square. The kitchen is fully equipped, the bed was comfortable and there are a lot of amenities and public transportation close by. I will definitely be staying hear again! "
United States
Lisa
The price is CA $121
CA $275 total
includes taxes & fees
Apr 19 - Apr 20
Nice 1BR Spot, Unwind & Relax

Navy Family home -Near Lake 4BR Hot Tub

Navy Family home -Near Lake 4BR Hot Tub
Gages Lake
10.0 out of 10, Exceptional, (8 reviews)
"The property was beautiful and relaxing. Our host was wonderful and responded quickly to any questions we had. "
United States
Danielle S.
The price is CA $212
CA $650 total
includes taxes & fees
Apr 20 - Apr 21
Navy Family home -Near Lake 4BR Hot Tub

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (66 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is CA $184
CA $449 total
includes taxes & fees
Apr 19 - Apr 20
2-bedroom apartment just 2 minutes drive to Wrigley Field

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (79 reviews)
"Had a lovely stay in a beautiful home! The setting is very secluded and quiet."
United States
Kyle M.
The price is CA $135
CA $269 total
includes taxes & fees
Apr 23 - Apr 24
Master qtr close to nature & easy urban facilities

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.0 out of 10, Wonderful, (14 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
The price is CA $124
CA $278 total
includes taxes & fees
Apr 27 - Apr 28
Charming Sunlit 1BR Apartment

Uptown Studio Gem Sum

Uptown Studio Gem Sum
Uptown
7.4 out of 10, Good, (6 reviews)
"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 CA $93
CA $226 total
includes taxes & fees
Apr 19 - Apr 20
Uptown Studio Gem Sum

Evanston Garden Guest House

Evanston Garden Guest House
North Evanston
10.0 out of 10, Exceptional, (1 review)
"Very friendly and hospitable. Always available to assist. Nice place. Highly recommend."
United States
Tracey B.
The price is CA $137
CA $274 total
includes taxes & fees
Apr 28 - Apr 29
Evanston Garden Guest House

Cozy & Furnished 2BR Unit

Cozy & Furnished 2BR Unit
Lincoln Square
9.2 out of 10, Wonderful, (19 reviews)
"Very cozy, amenities in great condition."
United States
Kaitlin T.
The price is CA $129
CA $310 total
includes taxes & fees
Apr 19 - Apr 20
Cozy & Furnished 2BR Unit

Chic 2BR Haven Near Irving Park

Chic 2BR Haven Near Irving Park
Irving Park
9.8 out of 10, Exceptional, (10 reviews)
"Ample accommodations for two adults. Clean and in great condition!"
United States
Kathy D.
The price is CA $141
CA $327 total
includes taxes & fees
Apr 19 - Apr 20
Chic 2BR Haven Near Irving Park

1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
7.6 out of 10, Good, (8 reviews)
"Great location, very clean. Easy check in and check out. Great communication."
United States
Thomas L.
The price is CA $99
CA $246 total
includes taxes & fees
Apr 19 - Apr 20
1BR/1BA City Comfort

Cozy apartment with AC and WiFi in awesome Chicago

Cozy apartment with AC and WiFi in awesome Chicago
Rogers Park
8.4 out of 10, Very good, (9 reviews)
"Cozy, private, clean. A quick walk to the train and busses. Would stay again."
United States
John D.
The price is CA $137
CA $427 total
includes taxes & fees
Apr 20 - Apr 21
Cozy apartment with AC and WiFi in awesome Chicago

Great Layout – Spacious 2BR Apt

Great Layout – Spacious 2BR Apt
Rogers Park
9.0 out of 10, Wonderful, (10 reviews)
"Clean, comfortable, and would definitely stay again!"
United States
KM W.
The price is CA $115
CA $291 total
includes taxes & fees
Apr 19 - Apr 20
Great Layout – Spacious 2BR Apt

Bright Garden Studio

Bright Garden Studio
South Evanston
8.2 out of 10, Very good, (33 reviews)
"Easy access. Nice location. Available shrot notice."
United States
Drew H.
The price is CA $105
CA $342 total
includes taxes & fees
Apr 22 - Apr 23
Bright Garden Studio

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (69 reviews)
"The home was a perfect spot for our family while we visited extended family. Quaint home and matched what was advertised online."
United States
Kayla C.
The price is CA $185
CA $459 total
includes taxes & fees
Apr 20 - Apr 21
Quaint Bungalow, near Great Lakes Naval Base

Cozy 2BR Apartment w/ Washer & Dryer

Cozy 2BR Apartment w/ Washer & Dryer
Portage Park
The price is CA $141
CA $327 total
includes taxes & fees
Apr 19 - Apr 20
Cozy 2BR Apartment w/ Washer & Dryer

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (45 reviews)
"The place was awesome - very clean !! Great location !! "
United States
John R.
The price is CA $142
CA $333 total
includes taxes & fees
Apr 28 - Apr 29
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Sunlit Studio with City Charm

Sunlit Studio with City Charm
Rogers Park
8.0 out of 10, Very good, (10 reviews)
"Host was extremely welcoming and accommodating. They went out of their way to assure me that they were but a call away if there was anything we needed."
United States
Renee W.
The price is CA $93
CA $226 total
includes taxes & fees
Apr 26 - Apr 27
Sunlit Studio with City Charm

Stylish and Roomy 2BR in Chicago

Stylish and Roomy 2BR in Chicago
Edgewater
9.0 out of 10, Wonderful, (14 reviews)
"Clean room, easy, check-in, great location"
United States
brent w.
The price is CA $124
CA $304 total
includes taxes & fees
Apr 23 - Apr 24
Stylish and Roomy 2BR in Chicago

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.4 out of 10, Exceptional, (69 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is CA $93
CA $199 total
includes taxes & fees
Apr 20 - Apr 21
Cozy studio in Andersonville Chicago
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

Find out more about Highwood

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Highwood. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Beach Park Estate: Chef's Kitchen, Nature, Fitness Room, Naval Base, Beach, Lake: This vacation home near Highwood offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

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 Rosewood Beach. 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.