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Highwood Vacation Rentals

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Vacation Rentals in Highwood

Private kitchen
Your Next Vacation Home
10.0 out of 10, Exceptional, (9)
"This home was very Beautiful and More Spacious than expected with a Beautiful back yard that we sadly didn’t get to enjoy because of the rain. The house location was great with A lot of stores and restaurants nearby. Next time we have a Family gathering I definitely will be rebooking"
The price is $160
$300 total
includes taxes & fees
May 28 - May 29
Your Next Vacation Home
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Excellent"
The price is $148
$190 total
includes taxes & fees
May 19 - May 20
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (156)
"We stayed here for our daughter's graduation. It was a perfect home base for everything we needed to do. Ross was attentive and thorough in explaining everything we needed to know about the unit, garage parking was a plus, beds were comfortable...overall a great stay."
Walking distance to restaurants, shops and Lake Michigan,
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Interior
Bright Garden Studio
9.4 out of 10, Exceptional, (3)
"Husband/wife/teen needed a place for a weekend stay near Northwestern. The teen slept on the couch and was comfortable. Street parking was never a problem. It IS a basement property and you can expect some noise from neighbors above, but it wasn’t overly intrusive during our stay. Host very responsive and accessible. Worked out great for our needs."
Bright Garden Studio
Interior
10 min walk to Stevenson Convention Center
10.0 out of 10, Exceptional, (1)
"I was attending a conference at the Donald Stephens Convention Center and this location was very convenient to both the event and numerous food/shopping options. Worked out very well and the property manager was easy to communicate with through the process."
10 min walk to Stevenson Convention Center
Smart TV, stereo
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.6 out of 10, Exceptional, (8)
"The proximity to Great Lakes Recruitment Center, Sarge’s Meet & Greet, restaurants, etc. is perfect. We were in town for our son’s boot camp graduation and knew we wanted more room to hang out than a typical hotel room would offer. It was great to be able to relax, watch movies, just hang out with our sailor for the precious two days we had. This place has location, location, location if you’re coming in for boot camp graduation."
The price is $121
$235 total
includes taxes & fees
May 19 - May 20
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Private kitchen
Fully Updated home. Great for the entire family!
7.6 out of 10, Good, (10)
"My impression of the inside was good. However the outside needs some work. Maybe some up grades in the furniture would be beneficial. Other then that it was an enjoyable experience Thank u"
Fully Updated home. Great for the entire family!
Beach nearby
Pet-Friendly Urban Chicago Vacation Rental Condo
9.6 out of 10, Exceptional, (5)
"Nice area with convenient access to the city, quiet in the evenings and a short walk from lake Michigan."
Pet-Friendly Urban Chicago Vacation Rental Condo
Private kitchen | Fridge, microwave, oven, stovetop
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
10.0 out of 10, Exceptional, (145)
"Kim’s place is in a quiet neighborhood, just a couple blocks from the Roscoe Village shops and restaurants. It was also an easy 20 minute walk from shops and restaurants in the Southport area and a 30 minute walk from Wrigley Field. We had no problems parking on the street throughout our stay. If you enjoy Cubs games and a variety of restaurants and shops, all within walking distance…then this is the place for you!"
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
Microwave
Charming Wrigleyville Home Close to the Cubs!
10.0 out of 10, Exceptional, (4)
"Location, location, and location GREAT Couple of blocks from Wrigley field. There was no place to sit and have a conversation or eat. A small table with chairs would be nice. Since there is no table it would have been nice to have a TV in both bedrooms. The bathroom is so spacious and the shower is wonderful. We loved it. We have give the information to several of of friends to use"
Charming Wrigleyville Home Close to the Cubs!
Interior
Light Filled with Tasteful Pops of Color - You Will Love This Mid-Century Modern Gem by RedAwning
10.0 out of 10, Exceptional, (9)
"Pictures are exactly as reality. Very spacious 3bdrm priced fairly. Excellent location (not in the HEART of action but close enough)- walking distance to El, coffee shop, restaurants, breweries and boutiques. City parking. Would suggest to others looking for clean, basic yet not junky 3 bedroom! A note to owner: the ship is not needed on the mantle :) we moved as soon as we opened the door! Let that beautiful fireplace shine! Would"
Light Filled with Tasteful Pops of Color - You Will Love This Mid-Century Modern Gem by RedAwning
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (177)
"We had a lovely time in Chicago, and Ross was very easy to communicate with."
Walking distance to restaurants, shops and Lake Michigan,
Fridge, microwave, oven, stovetop
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
9.2 out of 10, Wonderful, (15)
"we were a group of seven, aged 18 months to 66 years. the flat was great. with the three bedrooms, queen beds in two rooms, two twins in the other, plus a pack’n play for the youngest, everyone had a comfortable place to sleep. also great that we were able to make breakfast in the mornings! the neighborhood was fantastic! very friendly people, so quiet, plenty of on street parking (no permits required!!!) easy communication with the host. great price! we appreciated the welcome booklet. flat was...
The price is $189
$445 total
includes taxes & fees
May 23 - May 24
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Exterior
Breathtaking home close to Schaumburg, Chicago
9.8 out of 10, Exceptional, (37)
"It was a perfect location and plenty of space for family of 8 plus visiting friends. Mike was a great host and we got to enjoy some firewood he had set up for us to have a fire. Highly recommend! The description says 4 bathrooms and there are 3 bathrooms…the only discrepancy."
Breathtaking home close to Schaumburg, Chicago
Smart TV
Chic, Cozy home, by Blue Line Train Stop + Free parking
9.6 out of 10, Exceptional, (24)
"Close to blue line CTA. Quiet. Parking on street."
Chic, Cozy home, by Blue Line Train Stop + Free parking
Fridge, microwave, oven, stovetop
Perfectly Located, Bright 2B/1BA Urban Oasis
9.0 out of 10, Wonderful, (13)
"the host is very kind, the apartment is clean and the neighborhood is quiet. I recommend"
Perfectly Located, Bright 2B/1BA Urban Oasis
Fridge, microwave, oven, stovetop
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
10.0 out of 10, Exceptional, (54)
"Appartment worked well for us. Clean with everything we needed. Parking is on the street first come first serve. We were able to find a apot within the block."
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
TV
New Your Home Away From Home! - Near Great Lakes Naval Base!!
9.2 out of 10, Wonderful, (10)
"We were in North Chicago for PIR. It is less than 2 miles to the ceremony (we walked to avoid traffic and parking), there are ample rooms and beds for a family crew. Space to cook and serve and lounge about while your sailor decompresses. Restaurants are near enough (we got pizza from LouMalnatis in Gurnee), and grocery stores were close too. Communication was spot on, every time I had a question, they were on top of it (no issues, just questions)"
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Exterior
Urban Farmhouse near O’Hare Airport
9.2 out of 10, Wonderful, (28)
"The place fit the description and fit our needs perfectly. Host was very communicative and made everything very easy."
Urban Farmhouse near O’Hare Airport
Outdoor pool, a heated pool
Uptown studio apartment with breathing views
10.0 out of 10, Exceptional, (13)
"Check in was easy, no problems getting in or out. it would helpful to note in the listing that paid parking is across the street, $32/day, no in & out. Not a terrible price. Parking is very limited in the neighborhood. Overall, the stay went well!"
Uptown studio apartment with breathing views
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See all available properties in Highwood
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.

Other types of properties in Highwood you may be interested in

Lobby
Best Western At O'Hare
2.5 star property
7.4 out of 10, Good, (1804)
"Close to Airport "
The price is $110
$125 total
includes taxes & fees
May 21 - May 22
Best Western At O'Hare
Exterior
Hyatt Place Chicago/O'Hare Airport
3.0 star property
8.4 out of 10, Very Good, (2266)
"Great atay"
The price is $131
$154 total
includes taxes & fees
Jun 9 - Jun 10
Hyatt Place Chicago/O'Hare Airport
Indoor pool, outdoor pool
Marriott Chicago O'Hare
3.5 star property
8.2 out of 10, Very Good, (1002)
"The staff were so helpful and friendly, makes me want to come back. Great customer service. "
The price is $169
$198 total
includes taxes & fees
May 23 - May 24
Marriott Chicago O'Hare
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.

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 $119 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 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?

Your Next Vacation Home: This vacation home rental near Highwood has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 Ravinia Park. 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.

Recent reviews of Highwood properties
Expedia verified reviews

Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

5/5 Excellent
"I love the Bible in the nightstand. Please keep that. TJ and the shuttle driver and uno servers were friendly. "
A verified traveler stayed at Comfort Suites Chicago O'Hare Airport
Posted 22 hours ago
Comfort Suites Chicago O'Hare Airport