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Highwood Vacation Rentals

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Vacation Rentals in Highwood

Aparthotel in Downtown Evanston

3.5 star property
9.4 out of 10, Exceptional, (97)
"Great stay. The studio is small but has everything necessary."
United States
Julia
$182 nightly
The price is $208
Nov 30 - Dec 1
Total with taxes and fees
The Gem Museum Suites

Apartment in Edgewater

9.8 out of 10, Exceptional, (35)
"Had a great stay. Great location. "
United States
Justin
$130 nightly
The price is $160
Dec 1 - Dec 2
Total with taxes and fees
Relaxing Chicago Studio

Apartment in Edgewater

9.6 out of 10, Exceptional, (40)
"Great location & comfy space."
United States
Linda Z.
Luxurious 3 Bedroom Apartment in Chicago

Apartment in Edgewater

9.4 out of 10, Exceptional, (50)
"Great studio apartment. Needed just one night and worth the price. Would recommend."
United States
Sahm
$120 nightly
The price is $148
Dec 8 - Dec 9
Total with taxes and fees
Cozy studio in Andersonville Chicago

Vacation Home in Waukegan

2.0 star property
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.
$227 nightly
The price is $241
Dec 1 - Dec 2
Total with taxes and fees
Home -2 bedroom, 4k projector

Apartment in Ravenswood

9.8 out of 10, Exceptional, (20)
"Great stay"
United States
Kayla K.
$145 nightly
The price is $159
Dec 1 - Dec 2
Total with taxes and fees
Nice 1BR Spot, Unwind & Relax

Apartment in Lakeview

9.4 out of 10, Exceptional, (42)
"Great location and easy check in. "
United States
Fabio B.
Charming Wrigleyville Home Close to the Cubs!

Vacation Home in Riverwoods

9.8 out of 10, Exceptional, (73)
"Perfect secluded neighborhood. Very quiet which is what we needed to just get away from everything. Shopping and restaurants are all within 10 minutes. Owner always answered my questions right away. Would stay there again for a little retreat."
United States
Timothy
$184 nightly
The price is $195
Dec 1 - Dec 2
Total with taxes and fees
Master qtr close to nature & easy urban facilities

Vacation Home in Oakton

9.6 out of 10, Exceptional, (54)
"Clean and spacious, very gracious and responsive host, house is well-stocked. Quiet and safe area."
United States
Maricar W.
$282 nightly
The price is $302
Dec 1 - Dec 2
Total with taxes and fees
Your Next Vacation Home

Apartment in North Center

8.8 out of 10, Excellent, (13)
"Awesome "
United States
Robert
$145 nightly
The price is $159
Nov 30 - Dec 1
Total with taxes and fees
1BR Apartment in Chicago

Vacation Home in Palatine

9.8 out of 10, Exceptional, (77)
"very nice four bedroom home and a great location."
United States
Craig S.
Breathtaking home close to Schaumburg, Chicago

Apartment in 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

Apartment in Portage Park

9.6 out of 10, Exceptional, (5)
"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
$168 nightly
The price is $184
Dec 2 - Dec 3
Total with taxes and fees
Homey 2BR Apt w/ Parking

Vacation Home in North Chicago

10.0 out of 10, Exceptional, (13)
"Home was cute and as advertised, outdoor area great for families to relax. Only recommendation to have some information at the home for guests in the event the alarm system is activated so it can be acknowledged quickly. "
United States
Noel B.
$517 nightly
The price is $530
Nov 30 - Dec 1
Total with taxes and fees
North Chi retreatNavySaunaTiki BarGames

Apartment in Edgewater

9.2 out of 10, Wonderful, (25)
"Great walkable location. "
United States
Danielle G.
Serene 3-bedroom apartment in Chicago

Apartment in Portage Park

10.0 out of 10, Exceptional, (113)
"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!

Vacation Home in Lakeview

4.0 star property
9.4 out of 10, Exceptional, (43)
"Great spot to stay if you’re interested in Wrigleyville, no need to Uber for anything it was fantastic. "
United States
Anonymous traveler
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

Cottage in South Evanston

3.0 star property
Pet-friendly Abode, 2 Mi to Dtwn Evanston!

Vacation Home in Schaumburg

2.0 star property
10.0 out of 10, Exceptional, (3)
"Super comfy for families and the nicest host. "
United States
Anonymous traveler
$485 nightly
The price is $519
Dec 1 - Dec 2
Total with taxes and fees
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups

Apartment in North Center

2.0 star property
9.6 out of 10, Exceptional, (51)
"Nice property, great location, super helpful host!"
United States
Carin O.
$295 nightly
The price is $364
Nov 29 - Nov 30
Total with taxes and fees
2-bedroom apartment just 2 minutes drive to Wrigley Field
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

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.

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?

Master qtr close to nature & easy urban facilities: This vacation home rental near Highwood offers a garden, a hot tub, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware.

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.