Highwood Vacation Rentals

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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Highwood vacation rentals

Exterior detail

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (69 reviews)
"We had a great stay! The area was peaceful and felt safe. "
United States
Yoselin V.
$313 nightly
The price is $332
Apr 5 - Apr 6
Total with taxes and fees
Quaint Bungalow, near Great Lakes Naval Base
Iron/ironing board, WiFi

Uptown Studio Gem Sum

Uptown Studio Gem Sum
Uptown
7.4 out of 10, Good, (6 reviews)
"The neighborhood was perfect for me. I’d like to book the same property again because of the location.The only problem was checking in. The address was wrong and if I wasn’t raised in that part of Chicago I would have been very confused.Plus I checked in late at night. It wasn’t an easy process. Next time it will be diffeeent."
United States
Darryl C.
$145 nightly
The price is $161
Apr 5 - Apr 6
Total with taxes and fees
Uptown Studio Gem Sum
TV, offices

Cozy & Furnished 2BR Unit

Cozy & Furnished 2BR Unit
Lincoln Square
9.2 out of 10, Wonderful, (17 reviews)
"Very cozy, amenities in great condition."
United States
Kaitlin T.
$202 nightly
The price is $224
Apr 5 - Apr 6
Total with taxes and fees
Cozy & Furnished 2BR Unit
TV

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (31 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
$179 nightly
The price is $199
Apr 5 - Apr 6
Total with taxes and fees
Nice 1BR Spot, Unwind & Relax
Property grounds

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, (65 reviews)
"Great host, quick communication, and wonderful place to stay in Chicago. Well thought out and made our stay enjoyable. Highly recommend, we will book it again next time we are in Chicago. "
United States
Justin P.
$268 nightly
The price is $331
Apr 5 - Apr 6
Total with taxes and fees
2-bedroom apartment just 2 minutes drive to Wrigley Field
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
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.
$160 nightly
The price is $171
Apr 5 - Apr 6
Total with taxes and fees
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Property grounds

Evanston Garden Guest House

Evanston Garden Guest House
North Evanston
$197 nightly
The price is $199
Apr 6 - Apr 7
Total with taxes and fees
Evanston Garden Guest House
TV, offices

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.
$202 nightly
The price is $224
Apr 5 - Apr 6
Total with taxes and fees
Stylish and Roomy 2BR in Chicago
TV, offices

Great Layout – Spacious 2BR Apt

Great Layout – Spacious 2BR Apt
Rogers Park
8.8 out of 10, Excellent, (8 reviews)
"Clean, comfortable, and would definitely stay again!"
United States
KM W.
$208 nightly
The price is $231
Apr 5 - Apr 6
Total with taxes and fees
Great Layout – Spacious 2BR Apt
TV, offices

1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
7.2 out of 10, Good, (7 reviews)
"Great location, very clean. Easy check in and check out. Great communication."
United States
Thomas L.
$159 nightly
The price is $176
Apr 5 - Apr 6
Total with taxes and fees
1BR/1BA City Comfort
TV

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.
$212 nightly
The price is $235
Apr 5 - Apr 6
Total with taxes and fees
Chic 2BR Haven Near Irving Park
Exterior detail

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (78 reviews)
"Had a lovely stay in a beautiful home! The setting is very secluded and quiet."
United States
Kyle M.
$184 nightly
The price is $195
Apr 9 - Apr 10
Total with taxes and fees
Master qtr close to nature & easy urban facilities
Interior

Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
"Beautifully decorated, spotless unit. Conveniently located."
United States
Holly G.
$239 nightly
The price is $245
Apr 5 - Apr 6
Total with taxes and fees
Pine Beam Sloth Apartment next to Blue Line
1 bedroom, iron/ironing board, travel crib, WiFi

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.2 out of 10, Wonderful, (13 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
$182 nightly
The price is $203
Apr 8 - Apr 9
Total with taxes and fees
Charming Sunlit 1BR Apartment
2 bedrooms, iron/ironing board, travel crib, WiFi

Well-Equipped 2BR Unit with Parking

Well-Equipped 2BR Unit with Parking
North Evanston
10.0 out of 10, Exceptional, (3 reviews)
"Great place. Super clean and easy off street parking. Thanks !"
United States
Ann N.
$213 nightly
The price is $232
Apr 5 - Apr 6
Total with taxes and fees
Well-Equipped 2BR Unit with Parking
Fridge, microwave, oven, stovetop

Navy Family home -Near Lake 4BR Hot Tub

Navy Family home -Near Lake 4BR Hot Tub
Gages Lake
10.0 out of 10, Exceptional, (7 reviews)
"The property was beautiful and relaxing. Our host was wonderful and responded quickly to any questions we had. "
United States
Danielle S.
$459 nightly
The price is $470
Apr 5 - Apr 6
Total with taxes and fees
Navy Family home -Near Lake 4BR Hot Tub
Terrace/patio

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.0 out of 10, Wonderful, (20 reviews)
"Convenient check in and good amenities made this a pleasant place to stay near our relative in Chicago. "
United States
Laura O.
$230 nightly
The price is $277
Apr 5 - Apr 6
Total with taxes and fees
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.4 out of 10, Exceptional, (66 reviews)
"Great stay i loved it"
United States
Cedes W.
$113 nightly
The price is $139
Apr 6 - Apr 7
Total with taxes and fees
Cozy studio in Andersonville Chicago
Lobby

Bright Garden Studio

Bright Garden Studio
South Evanston
8.4 out of 10, Very Good, (32 reviews)
"Great spot. Very convenient and everything we needed for a long weekend visit to Evanston."
United States
William B.
$215 nightly
The price is $244
Apr 6 - Apr 7
Total with taxes and fees
Bright Garden Studio
TV, offices

Homey 1BR Space Apartment

Homey 1BR Space Apartment
Lincoln Square
9.6 out of 10, Exceptional, (16 reviews)
"Love the location right in Lincoln Square. "
United States
Ticia B.
$178 nightly
The price is $198
Apr 27 - Apr 28
Total with taxes and fees
Homey 1BR Space Apartment
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

Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

10/10 Excellent
"Yes"
Jaquetta 1-night trip
Posted 2 hours ago
Great Wolf Lodge Illinois

Find out more about Highwood

Everything you need to know about Highwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highwood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highwood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $139 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highwood rentals

At Expedia, we put the best Highwood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Highwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highwood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.