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Holiday Rentals in Highwood

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Holiday Rentals in Highwood

Warm & Stylish 2BR Apt

Albany Park
10.0 out of 10, Exceptional, (1)
"Met my expectations. Nice comfortable unit located in a great part of Chicago. Host was very responsive."
United States
Maureen B.
The price is €175
includes taxes & fees
15 Dec - 16 Dec
Warm & Stylish 2BR Apt

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Uptown
8.8 out of 10, Excellent, (18)
"Had a great stay! Perfect for our needs. Great location. It was an easy walk to the lake and lots of great restaurants nearby!"
United States
Rodney S.
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Comfortable 2BR Chicago Apt

Albany Park
9.6 out of 10, Exceptional, (4)
"Perfect location for our trip. Very functional and comfortable. "
United States
Michael
The price is €175
includes taxes & fees
15 Dec - 16 Dec
Comfortable 2BR Chicago Apt

Nice 1BR Spot, Unwind & Relax

Ravenswood
10.0 out of 10, Exceptional, (21)
"Great stay"
United States
Kayla K.
The price is €141
includes taxes & fees
2 Dec - 3 Dec
Nice 1BR Spot, Unwind & Relax

Cozy 1BR in Walkable Area

Ravenswood
9.8 out of 10, Exceptional, (7)
"We loved staying here! Would 100% stay again.Really clean and comfortable! Loved the mattress. Easy check in and out. Close to great businesses for dining or shopping. Close to the Brown line and a few buses for all our transit needs. Air-conditioned, thank god! There were all the amenities you expect like pots and pans, soap and shampoo in the shower, and even an iron and ironing board! We felt a lot like locals for our short 5 day stay!Basically perfect except for some small issues. The...
United States
Ariel k.
The price is €151
includes taxes & fees
15 Dec - 16 Dec
Cozy 1BR in Walkable Area

1BR Pad with Homey Feel

Ravenswood
10.0 out of 10, Exceptional, (2)
"Clean quiet apartment just a block away from the train! Very convenient and there's a Starbucks right down the street."
United States
Kevin D.
The price is €175
includes taxes & fees
15 Dec - 16 Dec
1BR Pad with Homey Feel

Cozy 3BR Gem in North Center

North Center
9.4 out of 10, Exceptional, (8)
"Great place to stay and host communicated quickly when needed. Will stay again on next trip to Chicago!"
United States
Alicia
The price is €209
includes taxes & fees
15 Dec - 16 Dec
Cozy 3BR Gem in North Center

2BR Getaway - Comfy & Ready

Rogers Park
9.6 out of 10, Exceptional, (8)
"Great location "
United States
Bernard M.
The price is €159
includes taxes & fees
14 Dec - 15 Dec
2BR Getaway - Comfy & Ready

Chic & Fully Furnished 2BR Apt!

Avondale
10.0 out of 10, Exceptional, (2)
"Our stay was great! The apartment is very clean and comfortable. Nicely furnished. On a residential street in a lovely neighborhood. Wifi and A/C units worked well (we were there in August). We found street parking pretty easily. And Kristine was a really responsive host. Would absolutely stay again!"
United States
Stephanie D.
The price is €174
includes taxes & fees
14 Dec - 15 Dec
Chic & Fully Furnished 2BR Apt!

Homey 2BR Apt w/ Parking

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
The price is €175
includes taxes & fees
9 Dec - 10 Dec
Homey 2BR Apt w/ Parking

Sunny Studio in Heart of Ravenswood

Uptown
9.4 out of 10, Exceptional, (6)
"It was a great stay if you want to experience a diverse, fun, authentic Chicago neigborhood. We really enjoyed it. "
United States
Amer
The price is €150
includes taxes & fees
14 Dec - 15 Dec
Sunny Studio in Heart of Ravenswood

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Uptown
10.0 out of 10, Exceptional, (48)
"Clean and quiet, perfect for nights to rest after exploring the city"
United States
Joe T.
The price is €211
includes taxes & fees
8 Dec - 9 Dec
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

1BR Apartment in Chicago

North Center
8.8 out of 10, Excellent, (13)
"Awesome "
United States
Robert
The price is €141
includes taxes & fees
2 Dec - 3 Dec
1BR Apartment in Chicago

Sleek and cozy 1BR Apartment

North Evanston
10.0 out of 10, Exceptional, (1)
"It was a great day. "
United States
Ann W.
Sleek and cozy 1BR Apartment

Trendy & Comfy Studio Unit

Portage Park
9.6 out of 10, Exceptional, (4)
"Older property. Landlord special in the bathroom. Definitely needs better window coverings. Otherwise, comfortable, safe, and clean. "
United States
Courtney V.
The price is €142
includes taxes & fees
15 Dec - 16 Dec
Trendy & Comfy Studio Unit

2BR Cozy & Functional Unit

Belmont Cragin
10.0 out of 10, Exceptional, (1)
"The host was available and helpful at check-in. The 2 bedroom apartment was clean and well stocked. We felt safe and at home. We slept well. We did not notice any street noise at night. We had more than we epected and everything we needed.It might be helpful to color code the keys with nail polish or something. The three locks to get into the unit felt like a struggle because we needed a quick turn around time between events. Otherwise, it was a great stay!!"
United States
Laura V.
The price is €175
includes taxes & fees
15 Dec - 16 Dec
2BR Cozy & Functional Unit

Relaxing Chicago Studio

Edgewater
9.8 out of 10, Exceptional, (36)
"Had a great stay. Great location. "
United States
Justin
The price is €132
includes taxes & fees
2 Dec - 3 Dec
Relaxing Chicago Studio

Prime City Stay in a 1BR Apt

Irving Park
9.2 out of 10, Wonderful, (11)
"Nice property "
United States
William S.
The price is €141
includes taxes & fees
2 Dec - 3 Dec
Prime City Stay in a 1BR Apt

Special Skevanston Space 2mi to Northwestern University & beach

Evanston
9.0 out of 10, Wonderful, (21)
"Very nice stay. Host was super nice and accommodating. "
United States
Melissa K.
The price is €191
includes taxes & fees
9 Dec - 10 Dec
Special Skevanston Space 2mi to Northwestern University & beach

Cozy & Furnished 2BR Unit

Ravenswood
9.0 out of 10, Wonderful, (13)
"Our star was short but good! Clean and comfortable beds!!"
United States
Melissa E.
The price is €161
includes taxes & fees
2 Dec - 3 Dec
Cozy & Furnished 2BR Unit
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Highwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Highwood holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highwood holiday rentals we have selected for you start as low as €126 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 holiday 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 holiday.

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 holiday rentals in Highwood?

Yes, there are holiday rentals close to the most popular sights in Highwood, or you can select a more secluded option if you're looking for a relaxing stay. Highwood is known for its shopping and restaurants.

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

Home -2 bedroom, 4k projector: This holiday home rental outside of 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 wider area, you’ll find Naval Base Great Lakes and Lake Forest College.

What are holiday rentals like in Highwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Highwood. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for a family trip.