Holiday Rentals in Highwood

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Our top choices for Highwood holiday rentals

Apartment in Irving Park

Charming Sunlit 1BR Apartment
9.2 out of 10, Wonderful, (12 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
The price is €154
includes taxes & fees
5 Mar - 6 Mar
Charming Sunlit 1BR Apartment

Apartment in North Evanston

Evanston Garden Guest House
The price is €172
includes taxes & fees
9 Mar - 10 Mar
Evanston Garden Guest House
9.6 out of 10, Exceptional, (59 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is €256
includes taxes & fees
5 Mar - 6 Mar
2-bedroom apartment just 2 minutes drive to Wrigley Field
9.8 out of 10, Exceptional, (77 reviews)
"Nice , private and peaceful definitely will be back "
United States
BRANDEN J.
The price is €170
includes taxes & fees
5 Mar - 6 Mar
Master qtr close to nature & easy urban facilities
9.2 out of 10, Wonderful, (5 reviews)
"Cleanliness. Roomy. Comfortable mattresses. Fluffy, white bath towels. Ample towel racks in bathrooms. Attentive hostess. Off street parking greatly appreciated but garage door opener should be operative."
United States
MARGARET L.
The price is €178
includes taxes & fees
11 Mar - 12 Mar
Lovely 2BR with Parking Near United Center & Wrigley
9.0 out of 10, Wonderful, (4 reviews)
"Amazing stay, great host! "
United States
Aaron L.
The price is €269
includes taxes & fees
5 Mar - 6 Mar
Tiny Home Retreat with hot tub

Apartment in Irving Park

Chic 2BR Haven Near Irving Park
9.8 out of 10, Exceptional, (10 reviews)
"Ample accommodations for two adults. Clean and in great condition!"
United States
Kathy D.
The price is €173
includes taxes & fees
9 Mar - 10 Mar
Chic 2BR Haven Near Irving Park
9.8 out of 10, Exceptional, (69 reviews)
"Really amazing place. Adorable house, plenty of space, conveniently located. Great linens on the beds & amenities in the bathroom. Owner was incredibly flexible and responsive and great to work here. Had three visitors from Europe and they absolutely loved the place and had a great time. Would 100% stay here again the next time we're in the area. "
United States
Erika H.
The price is €290
includes taxes & fees
4 Apr - 5 Apr
Quaint Bungalow, near Great Lakes Naval Base
10.0 out of 10, Exceptional, (4 reviews)
"Nice location for our family attending our daughter's graduation from Navy Basic at Great Lakes. "
United States
Judson S.
The price is €652
includes taxes & fees
5 Mar - 6 Mar
Newly remodeled Near Lake 4BR Hot Tub Navy Family home
10.0 out of 10, Exceptional, (6 reviews)
"Beautifully decorated, spotless unit. Conveniently located."
United States
Holly G.
The price is €211
includes taxes & fees
5 Mar - 6 Mar
Pine Beam Sloth Apartment next to Blue Line

Holiday Home in Lake Villa

Hot Tub Retreats
The price is €245
includes taxes & fees
17 Mar - 18 Mar
Hot Tub Retreats
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful property, great location, quiet, with plenty of curb parking directly in front. "
United States
carlos l.
The price is €484
includes taxes & fees
5 Mar - 6 Mar
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
10.0 out of 10, Exceptional, (2 reviews)
"The property was very clean and has a very relaxing feel to it. The owner was very responsive when I had any questions and was very helpful. "
United States
Caleb C.
The price is €206
includes taxes & fees
5 Mar - 6 Mar
Cute & Cozy, 1bd Condo Apartment/townhouse
8.4 out of 10, Very good, (7 reviews)
"Loved this sweet space tucked into a special neighborhood in the city. Space was clean & comfortable, wonderful shower & a nice respite from city life. "
United States
Ever
The price is €185
includes taxes & fees
16 Mar - 17 Mar
Ideal 2BR Getaway Close to Attractions
9.8 out of 10, Exceptional, (8 reviews)
"Nice little spot in the NW Suburbs. Great jumping off point for everything further North and points South."
United States
Thomas Z.
The price is €193
includes taxes & fees
25 Mar - 26 Mar
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

Apartment in Lincoln Square

Nice 1BR Spot, Unwind & Relax
9.8 out of 10, Exceptional, (27 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
The price is €154
includes taxes & fees
11 Mar - 12 Mar
Nice 1BR Spot, Unwind & Relax
10.0 out of 10, Exceptional, (2 reviews)
"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 €278
includes taxes & fees
16 Mar - 17 Mar
Chic & Fully Furnished 2BR Apartment
10.0 out of 10, Exceptional, (3 reviews)
"This was everything in the description and more! Pet friendly, clean, quiet, spacious, and well-stocked! Our only regret was not being able to enjoy the nice yard and firepit because of the frigid temperatures. Our host was responsive friendly, and helpful. Excellent experience all the way around!"
United States
David B.
The price is €191
includes taxes & fees
5 Mar - 6 Mar
Peaceful & Quiet. Close to Great Lakes, prime outlet, Winthrop Harbor Marina.

Apartment in Uptown

Uptown Studio Gem Sum
7.4 out of 10, Good, (6 reviews)
"The neighborhood was perfect for me. I’d like to book the same property again because of the location.The only problem was checking in. The address was wrong and if I wasn’t raised in that part of Chicago I would have been very confused.Plus I checked in late at night. It wasn’t an easy process. Next time it will be diffeeent."
United States
Darryl C.
The price is €171
includes taxes & fees
16 Mar - 17 Mar
Uptown Studio Gem Sum
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 €136 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?

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!: This holiday home rental outside of Highwood offers a furnished patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Rosewood Beach. 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.