Highwood Vacation Rentals

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Check prices for these dates

In two weeks
Apr 3 - Apr 5
In two months
May 15 - May 17
In three months
Jun 12 - Jun 14
In four months
Jul 10 - Jul 12

Our top choices for Highwood vacation rentals

TV

Apartment in Lincoln Square

Nice 1BR Spot, Unwind & Relax
9.8 out of 10, Exceptional, (28 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
$159 nightly
The price is $176
Mar 22 - Mar 23
Total with taxes and fees
Nice 1BR Spot, Unwind & Relax
Exterior detail

Vacation Home in Mundelein

Quaint Bungalow, near Great Lakes Naval Base
9.8 out of 10, Exceptional, (69 reviews)
"Really amazing place. Adorable house, plenty of space, conveniently located. Great linens on the beds & amenities in the bathroom. Owner was incredibly flexible and responsive and great to work here. Had three visitors from Europe and they absolutely loved the place and had a great time. Would 100% stay here again the next time we're in the area. "
United States
Erika H.
$310 nightly
The price is $329
Mar 22 - Mar 23
Total with taxes and fees
Quaint Bungalow, near Great Lakes Naval Base
Property grounds

Apartment in North Center

2-bedroom apartment just 2 minutes drive to Wrigley Field
9.6 out of 10, Exceptional, (64 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
$267 nightly
The price is $330
Mar 22 - Mar 23
Total with taxes and fees
2-bedroom apartment just 2 minutes drive to Wrigley Field
TV, offices

Apartment in Rogers Park

Great Layout – Spacious 2BR Apt
10.0 out of 10, Exceptional, (5 reviews)
"Clean, comfortable, and would definitely stay again!"
United States
KM W.
$193 nightly
The price is $213
Mar 22 - Mar 23
Total with taxes and fees
Great Layout – Spacious 2BR Apt
TV, offices

Apartment in Lincoln Square

Homey 1BR Space Apartment
9.6 out of 10, Exceptional, (15 reviews)
"Love the location right in Lincoln Square. "
United States
Ticia B.
$178 nightly
The price is $198
Mar 25 - Mar 26
Total with taxes and fees
Homey 1BR Space Apartment
TV, offices

Apartment in Lincoln Square

Cozy & Furnished 2BR Unit
9.2 out of 10, Wonderful, (17 reviews)
"Very cozy, amenities in great condition."
United States
Kaitlin T.
$185 nightly
The price is $203
Mar 29 - Mar 30
Total with taxes and fees
Cozy & Furnished 2BR Unit
Smart TV

Apartment in Barrington

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
9.8 out of 10, Exceptional, (8 reviews)
"Nice little spot in the NW Suburbs. Great jumping off point for everything further North and points South."
United States
Thomas Z.
$160 nightly
The price is $171
Mar 24 - Mar 25
Total with taxes and fees
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Fridge, microwave, oven, stovetop

Vacation Home in Gages Lake

Navy Family home -Near Lake 4BR Hot Tub
10.0 out of 10, Exceptional, (4 reviews)
"Nice location for our family attending our daughter's graduation from Navy Basic at Great Lakes. "
United States
Judson S.
$744 nightly
The price is $763
Mar 22 - Mar 23
Total with taxes and fees
Navy Family home -Near Lake 4BR Hot Tub
Iron/ironing board, WiFi

Apartment in Uptown

Uptown Studio Gem Sum
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.
$152 nightly
The price is $169
Mar 22 - Mar 23
Total with taxes and fees
Uptown Studio Gem Sum
2 bedrooms, iron/ironing board, travel crib, WiFi

Apartment in North Evanston

Well-Equipped 2BR Unit with Parking
10.0 out of 10, Exceptional, (3 reviews)
"Comfortable and immaculate. It was a great place to stay. Thank you!"
United States
Nancy V.
$193 nightly
The price is $209
Mar 23 - Mar 24
Total with taxes and fees
Well-Equipped 2BR Unit with Parking
Terrace/patio

Apartment in South Evanston

Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
10.0 out of 10, Exceptional, (8 reviews)
"Everything was as described. I would stay here again."
United States
Brent S.
$218 nightly
The price is $248
Mar 22 - Mar 23
Total with taxes and fees
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
TV, offices

Apartment in Edgewater

Stylish and Roomy 2BR in Chicago
9.0 out of 10, Wonderful, (14 reviews)
"Clean room, easy, check-in, great location"
United States
brent w.
$185 nightly
The price is $203
Mar 29 - Mar 30
Total with taxes and fees
Stylish and Roomy 2BR in Chicago
1 bedroom, iron/ironing board, free WiFi, bed sheets

Apartment in Edgewater

Cozy studio in Andersonville Chicago
9.4 out of 10, Exceptional, (66 reviews)
"Great stay i loved it"
United States
Cedes W.
$120 nightly
The price is $148
Mar 31 - Apr 1
Total with taxes and fees
Cozy studio in Andersonville Chicago
Living area

Apartment in Lincolnwood

Pet-Friendly 1BR Oasis Near Chicago Downtown
$181 nightly
The price is $194
Mar 22 - Mar 23
Total with taxes and fees
Pet-Friendly 1BR Oasis Near Chicago Downtown
Smart TV

Condo in Zion

Cute & Cozy, 1bd Condo Apartment/townhouse
10.0 out of 10, Exceptional, (2 reviews)
"The property was very clean and has a very relaxing feel to it. The owner was very responsive when I had any questions and was very helpful. "
United States
Caleb C.
$218 nightly
The price is $231
Mar 23 - Mar 24
Total with taxes and fees
Cute & Cozy, 1bd Condo Apartment/townhouse
Private kitchen

Apartment in Rogers Park

Cozy apartment with AC and WiFi in awesome Chicago
9.0 out of 10, Wonderful, (8 reviews)
"Cozy, private, clean. A quick walk to the train and busses. Would stay again."
United States
John D.
$210 nightly
The price is $259
Mar 30 - Mar 31
Total with taxes and fees
Cozy apartment with AC and WiFi in awesome Chicago
Exterior detail

Vacation Home in Riverwoods

Master qtr close to nature & easy urban facilities
9.8 out of 10, Exceptional, (78 reviews)
"Nice , private and peaceful definitely will be back "
United States
BRANDEN J.
$184 nightly
The price is $195
Mar 26 - Mar 27
Total with taxes and fees
Master qtr close to nature & easy urban facilities
TV

Apartment in Irving Park

Chic 2BR Haven Near Irving Park
9.8 out of 10, Exceptional, (10 reviews)
"Ample accommodations for two adults. Clean and in great condition!"
United States
Kathy D.
$196 nightly
The price is $216
Mar 24 - Mar 25
Total with taxes and fees
Chic 2BR Haven Near Irving Park
Living area

Vacation Home in Winthrop Harbor

Peaceful & Quiet. Close to Great Lakes, prime outlet, Winthrop Harbor Marina.
10.0 out of 10, Exceptional, (3 reviews)
"This was everything in the description and more! Pet friendly, clean, quiet, spacious, and well-stocked! Our only regret was not being able to enjoy the nice yard and firepit because of the frigid temperatures. Our host was responsive friendly, and helpful. Excellent experience all the way around!"
United States
David B.
$205 nightly
The price is $217
Apr 7 - Apr 8
Total with taxes and fees
Peaceful & Quiet. Close to Great Lakes, prime outlet, Winthrop Harbor Marina.
Interior

Apartment in Irving Park

Pine Beam Sloth Apartment next to Blue Line
10.0 out of 10, Exceptional, (6 reviews)
"Beautifully decorated, spotless unit. Conveniently located."
United States
Holly G.
$240 nightly
The price is $247
Mar 24 - Mar 25
Total with taxes and fees
Pine Beam Sloth Apartment next to Blue Line
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

Embassy Suites by Hilton Chicago North Shore Deerfield

Embassy Suites by Hilton Chicago North Shore Deerfield

10/10 Excellent
"Clean room "
Shenee 2-night trip
Posted 4 hours ago
Embassy Suites by Hilton Chicago North Shore Deerfield

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 $148 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.