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Highwood Vacation Rentals

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Vacation Rentals in Highwood

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (59)
"The breakfast was wonderful. Everyone was very nice and friendly."
The Gem Museum Suites

Bright Garden Studio

9.0 out of 10, Wonderful, (21)
"Great Location"
The price is CA $116
CA $332 total
includes taxes & fees
May 19 - May 20
Bright Garden Studio

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (12)
"It was such an amazing property. Short walk to Wrigley which was perfect for me and my friends!!!!!! Will be booking again in the future"
The price is CA $123
CA $339 total
includes taxes & fees
Apr 30 - May 1
2-bedroom apartment just 2 minutes drive to Wrigley Field

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (51)
"Great spot."
The price is CA $151
CA $268 total
includes taxes & fees
Apr 30 - May 1
Master qtr close to nature & easy urban facilities

"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "

6.0 out of 10, (1)
"Room clean, fitness room awful!! Have to request house keeping but they do not change sheets. Bar and restaurant bare minimum. They have a nice bar next to hotel(Not the-one located in the hotel) Would not stay again!"
The price is CA $137
CA $166 total
includes taxes & fees
Apr 30 - May 1
"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "

Charming Wrigleyville Home Close to the Cubs!

9.6 out of 10, Exceptional, (18)
"Hardest part of the experience was finding the front door. After that, we had a wonderful experience. The shower was awesome. "
Charming Wrigleyville Home Close to the Cubs!

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (25)
"If you are looking for a place to stay for bootcamp graduation this is a great place. It’s minutes from the base. The pictures are accurate and the house had plenty of space for five people. Close to shopping, fast food, and casino. "
The price is CA $187
CA $343 total
includes taxes & fees
May 5 - May 6
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

Entire 3 Bedroom Cozy Unit

9.2 out of 10, Wonderful, (12)
"This stay was perfect "
The price is CA $259
CA $422 total
includes taxes & fees
May 3 - May 4
Entire 3 Bedroom Cozy Unit

Elegant 3 Bedroom and 1 Bath Apartment

9.0 out of 10, Wonderful, (10)
"Very nice place - can easily fit quite a few people! Host was very accommodating, place was clean and comfortable. My friends and I had a great time! "
Elegant 3 Bedroom and 1 Bath Apartment

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (30)
"This is a really cute property close to a lot of neighborhood restaurants and bars. The host is really nice and even moved his car for us so we could have his spot when we arrived. We would definitely stay here again. "
Great 3 bedroom rental unit near Logan Square

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

9.2 out of 10, Wonderful, (23)
"Is about 2 miles from great lakes for graduation. Layout is different. Sleeps 11 seats 5 or 6 in the living room, big table...half bath in kitchen...is cold in the winter...have to park in the back...walk around to front.can parknon the street but not overnight. The main bathroom with tyb sbower is high but has handrail. It snowed while we were there...owner shoveled sidewalk once. Overall it suit our need..its not high end but it was nice. Plenty of towels...no wash clothes...clean.."
New Your Home Away From Home! - Near Great Lakes Naval Base!!

Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field

10.0 out of 10, Exceptional, (174)
"Well equipped APT on quiet streetOn street parking was no problemNice new appliancesBeds comfortableLinens niceGreat trip!Thank you!"
Roscoe Village Inn -Guesthouse - Walk to Chicago's Wrigley Field

Charming Home in Portage Park

Charming Home in Portage Park

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (175)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
Walking distance to restaurants, shops and Lake Michigan,

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

10.0 out of 10, Exceptional, (97)
"Just what we needed for our Beauty show convention in Rosemont. Great place, the host Jamie is awesome. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

Urban Chicago Vacation Rental Condo Near Beach!

9.2 out of 10, Wonderful, (18)
"The property was just as advertised. Street parking was not a problem. Had some issues with the window blinds, but the property owners were quick to respond to our concern. "
Urban Chicago Vacation Rental Condo Near Beach!

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

4.0 star property
9.4 out of 10, Exceptional, (39)
"The large number of bedrooms provides privacy for a lot of people."
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (53)
"Great home for a weekend in Palatine with family dinner. There's plenty of space to spread out and connect with family. The dining room was spacious and comfortable. We enjoyed our stay immensely "
Breathtaking home close to Schaumburg, Chicago

The Avondale Lower Level

9.6 out of 10, Exceptional, (37)
"This was the second time we stayed in the garden apt. Jeds place is right around the block from our Chicago Family. Apt is we well located for shops/restaurants. We noticed the updates. Looking good. Everything you need is there. Comfortable/homey/clean. "
The Avondale Lower Level

Your Chicago Home Base – 4BR, 2BA, Sleeps 13, Ideal for Families & Groups!

Your Chicago Home Base – 4BR, 2BA, Sleeps 13, Ideal for Families & Groups!
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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Other types of properties in Highwood you may be interested in

Hyatt Regency O'Hare Chicago

4.0 star property
8.6 out of 10, Excellent, (1525)
"Clean!"
The price is CA $210
CA $240 total
includes taxes & fees
May 19 - May 20
Hyatt Regency O'Hare Chicago

Marriott Chicago O'Hare

3.5 star property
8.4 out of 10, Very good, (1019)
"Nice property. Clean."
The price is CA $234
CA $275 total
includes taxes & fees
May 23 - May 24
Marriott Chicago O'Hare

Hilton Chicago O'Hare Airport

4.0 star property
8.0 out of 10, Very good, (2032)
"Nice fast check in, convenient location"
The price is CA $298
CA $350 total
includes taxes & fees
May 24 - May 25
Hilton Chicago O'Hare Airport
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.

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?

Charming Home in Portage Park: 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 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.