Photo by Tara Jabbari

Highwood Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 15 - Dec 16
Tomorrow
Dec 16 - Dec 17
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for Highwood vacation rentals

Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher
The Gem Museum Suites

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (98)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is ￥28,326
￥32,428 total
includes taxes & fees
Dec 17 - Dec 18
The Gem Museum Suites
Desk, iron/ironing board, WiFi, bed sheets
Relaxing Chicago Studio

Relaxing Chicago Studio

Relaxing Chicago Studio
Edgewater
9.8 out of 10, Exceptional, (40)
"Had a great stay. Great location. "
United States
Justin
The price is ￥8,570
￥23,071 total
includes taxes & fees
Dec 16 - Dec 17
Relaxing Chicago Studio
1 bedroom, iron/ironing board, free WiFi, bed sheets
Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (54)
"Great location."
United States
Diane P.
The price is ￥10,128
￥22,111 total
includes taxes & fees
Dec 17 - Dec 18
Cozy studio in Andersonville Chicago
Microwave, oven, stovetop, dishwasher
Luxurious 3 Bedroom Apartment in Chicago

Luxurious 3 Bedroom Apartment in Chicago

Luxurious 3 Bedroom Apartment in Chicago
Edgewater
9.6 out of 10, Exceptional, (43)
"It was quite cold in Chicago during our stay, but the apartment was nice and warm! The space is huge and the hosts were very communicative. The location is great - lots of food options and the L nearby. The apartment felt fairly clean overall, but the towels and sheets were a bit stained and the floors and doors were a bit squeaky. Overall, it is a great place to stay for a trip of any length!"
United States
Debbie
Luxurious 3 Bedroom Apartment in Chicago
Property grounds
Walk to Wrigley Field! Townhouse w/ Pool Table

Walk to Wrigley Field! Townhouse w/ Pool Table

Walk to Wrigley Field! Townhouse w/ Pool Table
2.0 star property
Lakeview
The price is ￥27,267
￥105,219 total
includes taxes & fees
Dec 16 - Dec 17
Walk to Wrigley Field! Townhouse w/ Pool Table
TV
Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.6 out of 10, Exceptional, (25)
"Great stay"
United States
Kayla K.
The price is ￥9,816
￥26,251 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Nice 1BR Spot, Unwind & Relax
Microwave, oven, stovetop, dishwasher
Home -2 bedroom, 4k projector

Home -2 bedroom, 4k projector

Home -2 bedroom, 4k projector
2.0 star property
Waukegan
10.0 out of 10, Exceptional, (2)
"The host was so amazing! Made many accommodations to make my stay very enjoyable! The host was very responsive and available. I would recommend this home on Vrbo to anyone having to go to Great Lakes Illinois. I was able to attend my son’s Navy graduation which wasn’t far from this location. Great stay! "
United States
You Tha Truth B.
The price is ￥15,581
￥37,483 total
includes taxes & fees
Dec 19 - Dec 20
Home -2 bedroom, 4k projector
Exterior detail
Charming Wrigleyville Home Close to the Cubs!

Charming Wrigleyville Home Close to the Cubs!

Charming Wrigleyville Home Close to the Cubs!
Lakeview
9.4 out of 10, Exceptional, (44)
"Great location and easy check in. "
United States
Fabio B.
Charming Wrigleyville Home Close to the Cubs!
Fridge, microwave, oven, stovetop
North Chi retreatNavySaunaTiki BarGames

North Chi retreatNavySaunaTiki BarGames

North Chi retreatNavySaunaTiki BarGames
North Chicago
10.0 out of 10, Exceptional, (14)
"love the air hocky what a fun way to spend time with the kids! and after a long drive the sauna was a blessing. Also the fire pit and swings was the best way to end our day and spend time together."
United States
Chad H.
The price is ￥34,434
￥80,294 total
includes taxes & fees
Jan 4 - Jan 5, 2026
North Chi retreatNavySaunaTiki BarGames
Fridge, microwave, oven, stovetop
Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!

Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!

Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
Gurnee
9.8 out of 10, Exceptional, (23)
"It was perfect for our family. We all had beds to sleep in, they were comfortable and it was just minutes away from Great America. "
United States
Sherri K.
Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
Dining tables
New Your Home Away From Home! - Near Great Lakes Naval Base!!

New Your Home Away From Home! - Near Great Lakes Naval Base!!

New Your Home Away From Home! - Near Great Lakes Naval Base!!
North Chicago
9.2 out of 10, Wonderful, (35)
"Host was very hospitable and the house was clean."
United States
Ron R.
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Interior
Great Location-Beautiful Friendly Andersonville Neighborhood

Great Location-Beautiful Friendly Andersonville Neighborhood

Great Location-Beautiful Friendly Andersonville Neighborhood
Uptown
10.0 out of 10, Exceptional, (196)
"It was very nice - just as described.We loved the location- quiet street near so many things"
United States
Kathy B.
Great Location-Beautiful Friendly Andersonville Neighborhood
1 bedroom, iron/ironing board, travel crib, WiFi
1BR Apartment in Chicago

1BR Apartment in Chicago

1BR Apartment in Chicago
North Center
8.8 out of 10, Excellent, (15)
"Awesome "
United States
Robert
The price is ￥9,816
￥26,251 total
includes taxes & fees
Jan 1 - Jan 2, 2026
1BR Apartment in Chicago
Property grounds
Beach Park Estate: Chef's Kitchen, Nature, Fitness Room, Naval Base, Beach, Lake

Beach Park Estate: Chef's Kitchen, Nature, Fitness Room, Naval Base, Beach, Lake

Beach Park Estate: Chef's Kitchen, Nature, Fitness Room, Naval Base, Beach, Lake
2.0 star property
Beach Park
10.0 out of 10, Exceptional, (2)
"We rented the property to attend my daughter's RTC graduation. We have a big family so it was perfect. We had more than enough space and the house had lots of amenities so we didn't have to leave the house. We took advantage of the grill. the game room, the movie theater and decor with professional family photos."
United States
Chanda C.
Beach Park Estate: Chef's Kitchen, Nature, Fitness Room, Naval Base, Beach, Lake
Fridge, microwave, oven, stovetop
Family frndly TwnHm by navy base

Family frndly TwnHm by navy base

Family frndly TwnHm by navy base
2.0 star property
Waukegan
9.8 out of 10, Exceptional, (31)
"Nice property, very clean, comfortable beds, 10 minutes from Great Lakes base."
United States
Patrick K.
Family frndly TwnHm by navy base
Dining
The Greenleaf House—Whole House

The Greenleaf House—Whole House

The Greenleaf House—Whole House
Rogers Park
9.6 out of 10, Exceptional, (35)
"Great location for our stay and we enjoyed it. Only drawback was not being able to get college football on the tv on Saturday; but perhaps that was user error."
United States
John T.
The Greenleaf House—Whole House
House (2 Bedrooms) | Interior
Pet-friendly Abode, 2 Mi to Dtwn Evanston!

Pet-friendly Abode, 2 Mi to Dtwn Evanston!

Pet-friendly Abode, 2 Mi to Dtwn Evanston!
3.0 star property
South Evanston
Pet-friendly Abode, 2 Mi to Dtwn Evanston!
Fridge, microwave, oven, stovetop
8Beds, 2Queen, 3Twin, 2Sofa sleepers. Min. to O’hare & Allstate. Free parking

8Beds, 2Queen, 3Twin, 2Sofa sleepers. Min. to O’hare & Allstate. Free parking

8Beds, 2Queen, 3Twin, 2Sofa sleepers. Min. to O’hare & Allstate. Free parking
Franklin Park
8.6 out of 10, Excellent, (10)
"Overall it was a great VRBO. "
United States
Amy G.
8Beds, 2Queen, 3Twin, 2Sofa sleepers. Min. to O’hare & Allstate. Free parking
Fridge, oven, stovetop, toaster
Homey 2BR Apt w/ Parking

Homey 2BR Apt w/ Parking

Homey 2BR Apt w/ Parking
Portage Park
9.8 out of 10, Exceptional, (6)
"It was clean and well maintained unit. It’s next to grocery store and pharmacy which was very convenient. It’s not too far from downtown. I would stay again here in future if available."
United States
Jatin
The price is ￥11,218
￥30,230 total
includes taxes & fees
Dec 18 - Dec 19
Homey 2BR Apt w/ Parking
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!

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
Portage Park
10.0 out of 10, Exceptional, (115)
"Very nice place to stay. Host was very friendly and helpful."
United States
JoEllen P.
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highwood Hotel Reviews

Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

10/10 Excellent
"Maggie was great and very accommodating. After what seemed like an eternity of failed attempts of getting home today. United ended up not loading our luggage! However, Maggie to the rescue with toothbrushes, deodorant and makeup remover! "
LOANNA 1-night trip
Posted 16 hours ago
Loews Chicago O'Hare Hotel

Find out more about Highwood

Search for holiday rentals in Highwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Highwood using one of the methods below:

  • View our selection of featured holiday rentals in Highwood
  • Use the map to find apartments and other holiday homes in the Highwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Highwood while they last

Look no further and take a look at our great range of rental properties in Highwood!

Frequently asked questions

Are there vacation rentals in Highwood?

Yes, there are vacation rentals close to the most popular local attractions in Highwood, or you can choose a more secluded option if you'd like a relaxing place to stay. Highwood is known for its shopping and restaurants.

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

Home -2 bedroom, 4k projector: This vacation home rental near Highwood has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

What can I see and do in Highwood?

While exploring the area, visit family-friendly sights like Northbrook Sports Complex, 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.