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Highwood Vacation Rentals

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Vacation Rentals in Highwood

Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is CA $234
CA $297 total
includes taxes & fees
May 28 - May 29
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Private kitchen
Your Next Vacation Home
10.0 out of 10, Exceptional, (10)
"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 CA $266
CA $465 total
includes taxes & fees
Jun 3 - Jun 4
Your Next Vacation Home
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
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Interior
Bright Garden Studio
9.0 out of 10, Wonderful, (4)
"I'm a seminary student, and I came into town for an intensive class. So, I was really only in the space in the evenings, but it was comfy. The location is amazing!!! The studio apartment was decently clean. The projector is VERY cool. There were a few details I could not find instructions for, like where to take the garbage out when I was on my way out. But I left a message for the owner and they were good about it. I would stay again. Recommend."
Bright Garden Studio
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 CA $368
CA $747 total
includes taxes & fees
Jun 3 - Jun 4
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
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 CA $171
CA $327 total
includes taxes & fees
Jun 3 - Jun 4
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Beach nearby
Pet-Friendly Urban Chicago Vacation Rental Condo
9.8 out of 10, Exceptional, (6)
"Great and very clean place for our daughter’s graduation week."
Pet-Friendly Urban Chicago Vacation Rental Condo
Terrace/patio
Roxan Corner
9.0 out of 10, Wonderful, (18)
"This duplex was perfect for my three sons and myself. We stayed five days to attend one of my son’s Navy Graduation! House was very clean and modern. Had everything we needed, was a nice neighborhood, quiet neighbors? Close to everywhere we needed to go. Only suggestion would be to have the owners secure the rugs, they are very slippery. "
Roxan Corner
Exterior
Epic Lake Views Await You - You Will WANT to Wake up Early for the Sunrise by RedAwning
8.6 out of 10, Excellent, (15)
"Place was clean and beds were great. Very nice kitchen and being in the water is neat. The location is perfect for someone who doesn’t care if it’s off the beaten path a little. Parking is tough after 8pm. That would be my only complaint."
Epic Lake Views Await You - You Will WANT to Wake up Early for the Sunrise by RedAwning
Fridge, microwave, oven, dishwasher
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by RedAwning
9.6 out of 10, Exceptional, (19)
"Close to everything"
PET FRIENDLY! Unique Converted Storefront Stay - Great Neighborhood! by RedAwning
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Microwave
Charming Wrigleyville Home Close to the Cubs!
8.8 out of 10, Excellent, (5)
"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!
Fridge, microwave, oven, stovetop
Luxe Haus of Love—Renovated 1938 Cape Cod |Heated FLRS |420+
10.0 out of 10, Exceptional, (12)
"We loved staying at this property. We always opt for VRBO and other home rentals when we travel and I always do extensive research on each property/neighborhood before I book. This property ranks as one of our top experiences and we've traveled all over the world. The home itself is lavishly renovated and comfortably appointed. TONS of sleeping options, many sparklingly clean bathrooms, two dining areas, two sitting areas, a lovely (and quiet) backyard, and an impressive kitchen all with...
The price is CA $739
CA $1,248 total
includes taxes & fees
Jun 2 - Jun 3
Luxe Haus of Love—Renovated 1938 Cape Cod |Heated FLRS |420+
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
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, (56)
"We were very impressed. A very clean beautiful home. Had all the convenience of home. I definitely would recommend staying here. I give 5plus stars"
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
Private kitchen
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
10.0 out of 10, Exceptional, (146)
"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
Property grounds
The Lake House-2br/2bth - 50 steps from the beach!
10.0 out of 10, Exceptional, (20)
"This apartment was perfect for visiting our daughter at Loyola University. Very close to campus, transportation and food. The apartment was clean and had everything we needed. We would stay again!"
The Lake House-2br/2bth - 50 steps from the beach!
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (178)
"Beautiful and spacious unit with everything you could ask for. There were 5 of us and we had plenty of space to spread out and be comfortable. Great hospitality and Ross met us for checkin even though our flight had been delayed. Wonderful location and within walking distance of restaurants, shops and the CTA station (Howard). Would definitely stay again."
Walking distance to restaurants, shops and Lake Michigan,
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
TV
New Your Home Away From Home! - Near Great Lakes Naval Base!!
9.4 out of 10, Exceptional, (11)
"We really enjoyed the house, its very confortable, clean and the rooms are big. The house is very close to the base. Thanks."
New Your Home Away From Home! - Near Great Lakes Naval Base!!
Don't see what you're looking for?
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

Terrace/patio
Hilton Chicago O'Hare Airport
4.0 star property
7.6 out of 10, Good, (1974)
"The closeness to the airport for an early flight and the ease of access"
The price is CA $261
CA $307 total
includes taxes & fees
Jun 21 - Jun 22
Hilton Chicago O'Hare Airport
Lobby
Best Western At O'Hare
2.5 star property
7.4 out of 10, Good, (1861)
"It is a nice hotel with a very cooperative staff"
The price is CA $149
CA $170 total
includes taxes & fees
May 28 - May 29
Best Western At O'Hare
Indoor pool, outdoor pool
Marriott Chicago O'Hare
3.5 star property
8.2 out of 10, Very good, (1014)
"The staff were so helpful and friendly, makes me want to come back. Great customer service. "
The price is CA $231
CA $271 total
includes taxes & fees
Jun 14 - Jun 15
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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highwood vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highwood vacation rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard 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

Best Western At O'Hare

Best Western At O'Hare

5/5 Excellent
"It is a nice hotel with a very cooperative staff"
A verified traveller stayed at Best Western At O'Hare
Posted 16 hours ago
Best Western At O'Hare