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Highwood Vacation Rentals

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Oct 24 - Oct 25
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Oct 31 - Nov 2

Vacation Rentals in Highwood

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, (47)
"Great place to stay when you’re in town for the Cubbies! "
United States
Eric
$275 nightly
The price is $339
Oct 29 - Oct 30
Total with taxes and fees
2-bedroom apartment just 2 minutes drive to Wrigley Field
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, (93)
"Super nice hotel and staff "
United States
EMILY
$198 nightly
The price is $227
Nov 12 - Nov 13
Total with taxes and fees
The Gem Museum Suites
Fridge, microwave, oven, stovetop
Haus Of Hues: MDRN Bright Peaceful Private Apt
Haus Of Hues: MDRN Bright Peaceful Private Apt
2.0 star property
9.4 out of 10, Exceptional, (14)
"Nice quiet part of town with easy access to different parts of the city. Great communication before and during our stay. Definitely enjoyed our time. "
United States
Ali A.
$479 nightly
The price is $545
Oct 25 - Oct 26
Total with taxes and fees
Haus Of Hues: MDRN Bright Peaceful Private Apt
Fridge, microwave, oven, stovetop
Stunning & Stylish Downtown Studio - Highland Park
Stunning & Stylish Downtown Studio - Highland Park
2.0 star property
8.8 out of 10, Excellent, (6)
"Everything was as described. Parking is secure. Location is quiet, inside a nice neighborhood "
United States
Alissa S.
$154 nightly
The price is $163
Nov 3 - Nov 4
Total with taxes and fees
Stunning & Stylish Downtown Studio - Highland Park
Fridge, microwave, oven, stovetop
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
10.0 out of 10, Exceptional, (34)
"Lovely property, well equipped and a responsive host! Would definitely recommend."
United States
Bryan S.
$686 nightly
The price is $734
Nov 23 - Nov 24
Total with taxes and fees
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Fridge, microwave, oven, stovetop
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
9.6 out of 10, Exceptional, (24)
"The property was great. Clean, charming, and full of accommodations. Check in/out was really simple if you need a quick place to crash, but has everything you need for a longer stay. The best part was the communication with the host though. Very easy to get in touch with, very detailed in answering questions, and was understanding when discussing damage found from a previous guest. Overall would stay again. "
United States
Alex P.
$406 nightly
The price is $461
Oct 27 - Oct 28
Total with taxes and fees
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Exterior detail
Master qtr close to nature & easy urban facilities
Master qtr close to nature & easy urban facilities
9.8 out of 10, Exceptional, (69)
"Beautiful, quiet space."
United States
Mary
$175 nightly
The price is $186
Nov 3 - Nov 4
Total with taxes and fees
Master qtr close to nature & easy urban facilities
Dining
Quaint Bungalow, near Great Lakes Naval Base
Quaint Bungalow, near Great Lakes Naval Base
9.8 out of 10, Exceptional, (65)
"Great place and great price. Lots of restaurants around. Minutes from the highway for city access."
United States
Joseph B.
$313 nightly
The price is $332
Oct 26 - Oct 27
Total with taxes and fees
Quaint Bungalow, near Great Lakes Naval Base
Paper towels
Just remodeled apartment close to airport and mall
Just remodeled apartment close to airport and mall
10.0 out of 10, Exceptional, (14)
"Location was close to airport, restaurants and shopping"
United States
Dorothy J.
$237 nightly
The price is $254
Oct 26 - Oct 27
Total with taxes and fees
Just remodeled apartment close to airport and mall
1 bedroom, desk, iron/ironing board, travel crib
Bright Garden Studio
Bright Garden Studio
8.4 out of 10, Very Good, (29)
"Great spot. Very convenient and everything we needed for a long weekend visit to Evanston."
United States
William B.
$248 nightly
The price is $282
Oct 28 - Oct 29
Total with taxes and fees
Bright Garden Studio
Terrace/patio
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
10.0 out of 10, Exceptional, (40)
"We really enjoyed or stay at the apartment. Very quiet and nice location in a neighborhood."
United States
KAREN H.
$196 nightly
The price is $223
Oct 26 - Oct 27
Total with taxes and fees
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Fridge, microwave, oven, stovetop
Near Lake 4BR w/ Hot Tub & Games | LCP Collection
Near Lake 4BR w/ Hot Tub & Games | LCP Collection
9.8 out of 10, Exceptional, (17)
"Great property overall. The host was very accommodating and I highly recommend. "
United States
Jamie H.
$619 nightly
The price is $656
Nov 10 - Nov 11
Total with taxes and fees
Near Lake 4BR w/ Hot Tub & Games | LCP Collection
Private kitchen
Value Stay: Home - 2 Bedrooms
Value Stay: Home - 2 Bedrooms
2.0 star property
$229 nightly
The price is $243
Oct 26 - Oct 27
Total with taxes and fees
Value Stay: Home - 2 Bedrooms
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.
$353 nightly
The price is $374
Nov 3 - Nov 4
Total with taxes and fees
Charming 3-bedroom house in Grayslake
Fridge, microwave, stovetop, coffee/tea maker
Chic Studio - In Downtown Highland Park, by Metra
Chic Studio - In Downtown Highland Park, by Metra
8.4 out of 10, Very Good, (16)
"I enjoyed my stay at this property. It is in a great location, very unique and super clean! The host is really kind and helpful. "
United States
Deborah
$135 nightly
The price is $143
Nov 3 - Nov 4
Total with taxes and fees
Chic Studio - In Downtown Highland Park, by Metra
Smart TV
Getaway Near ORD With Great Local Amenities
Getaway Near ORD With Great Local Amenities
8.8 out of 10, Excellent, (3)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
United States
Stephanie G.
$261 nightly
The price is $276
Oct 28 - Oct 29
Total with taxes and fees
Getaway Near ORD With Great Local Amenities
Fridge, microwave, oven, stovetop
Wonderful in Wood Dale, right by O’Hare airport!
Wonderful in Wood Dale, right by O’Hare airport!
10.0 out of 10, Exceptional, (14)
"Great property and great host!"
United States
Darin H.
$374 nightly
The price is $396
Oct 26 - Oct 27
Total with taxes and fees
Wonderful in Wood Dale, right by O’Hare airport!
Private kitchen
Your Next Vacation Home
Your Next Vacation Home
9.6 out of 10, Exceptional, (54)
"We enjoyed our stay"
United States
Lukose K.
$285 nightly
The price is $305
Oct 26 - Oct 27
Total with taxes and fees
Your Next Vacation Home
Fridge, microwave, oven, stovetop
Gurnee home with King Queen beds for Vacations,six flags Celebrate Eid, Navy GL
Gurnee home with King Queen beds for Vacations,six flags Celebrate Eid, Navy GL
8.4 out of 10, Very Good, (7)
"Excellent location "
United States
Anthony N.
$994 nightly
The price is $1,053
Oct 25 - Oct 26
Total with taxes and fees
Gurnee home with King Queen beds for Vacations,six flags Celebrate Eid, Navy GL
Fridge, microwave, oven, stovetop
Special Skevanston Space 2mi to Northwestern University & beach
Special Skevanston Space 2mi to Northwestern University & beach
9.0 out of 10, Wonderful, (21)
"Me, my friends, and girlfriend all stayed here together for the weekend. We attended collect-a-con over in Rosemont and then also did a little day trip to downtown Chicago for mine and my friends birthday! It was really nice staying here, super cozy and cute. Very nice neighborhood and neighbors were friendly :)"
United States
Triston W.
$204 nightly
The price is $218
Nov 17 - Nov 18
Total with taxes and fees
Special Skevanston Space 2mi to Northwestern University & beach
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

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

10/10 Excellent
"I love it"
Robert 7-night trip
Posted 2 days ago
Motel 6 Elk Grove Village, IL - O'Hare

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 $142 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?

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.