We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals in Highwood

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Highwood

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Home in Highland Park

4.91 out of 5 average rating, 110 reviews

Rejuvenate and Relax in the North Shore

Set in the midst of an affluent neighborhood, this spacious and sunny four bedroom retreat offers all the comforts of a home away from home. With it's perfect location close to Lake Michigan, Chicago Botanical Garden, Ravinia, Naval Base, and Six Flags Great America to name a few, our family home is within reach to Chicago as well. If you feel very adventurous, just leave your car in garage, pick up a bike and ride the Lake Shore Bike trail all the way to downtown Chicago, enjoying the beautiful scenery. If you feel less adventures but still would like to enjoy beautiful scenery, you can do it by taking a train. Metra can get you downtown Chicago in less than 45 min. and the stop is within walking distance.

Sep 19 – 26

R9,770 ZAR per night

Loft in West Dundee

4.97 out of 5 average rating, 446 reviews

Hip Urban Loft - Small Town Charm - 124 LOFTS #2

Luxury one-bedroom loft in the heart of downtown Dundee. Newly renovated 125-year-old building with timber ceilings, exposed brick walls and beautifully restored hardwood floors. Tastefully decorated and features a king-size Beautyrest mattress, luxury bed linen, private bathroom, kitchenette with under counter refrigerator, Kuerig coffee maker and lightning fast Wi-Fi for streaming your favorite shows on the 60” LED smart TV. 124 LOFTS offers 4 separate luxury lofts. Loft 2 is our most spacious

Apr 1 – 8

R2,537 ZAR per night

Home in Highland Park

4.98 out of 5 average rating, 59 reviews

Charming Ranch-Style Cottage

Escape the hustle and bustle of the city in this relaxing, cozy, cottage that is a few blocks away from downtown Highland Park and Highwood, with great restaurants, bars and coffee shops. It is perfect for single travelers, couples, or a small family. We are grateful for the amazing Airbnb hosts across the globe, who opened their homes to us, and made our trips so memorable. So when we bought our own home, it was only right that we would return the favor and open our home to fellow adventurers

Feb 20 – 27

R3,155 ZAR per night

Home in Beach Park

4.98 out of 5 average rating, 161 reviews

B’s Farmhouse Cottage 2-bedroom duplex.

Experience the best of the midwest! Enjoy a newly remodeled "Magnolia Farm" inspired 2-bedroom duplex, all to yourself near everything you need. 50 Miles from Milwaukee, miles from Chicago, and 2 miles having your toes in the sand at Lake Michigan. We are minutes away from the Great Lakes Naval Station and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here make J&B's Farmhouse Cottage your home away from home today.

Apr 25 – May 2

R2,449 ZAR per night

Apartment in Highland Park

4.94 out of 5 average rating, 122 reviews

Lovely studio near the beach! (and heated floors!)

Get away from the city to this studio in Highland Park. The newly renovated space has everything you need for a relaxing getaway—huge comfy couch, brand new bed with Brooklinen + Parachute bedding, pristine bathroom, and lots of amenities. Downtown Highland Park, Highwood, + the beach are just a walk away. There's access to grocery stores, restaurants, and shops, and you can retreat to the quiet of your studio when you're ready to unwind. Ps. For the winter months: We've got heated floors.

Sep 13 – 20

R3,843 ZAR per night

Guest suite in Riverwoods

4.95 out of 5 average rating, 304 reviews

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

May 20 – 25

R2,919 ZAR per night

Home in Highland Park

4.9 out of 5 average rating, 125 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Experience luxury of this award winning 6BR 4Bath family home in picturesque Northshore private estate. Spend day by the private heated pool, enjoy beauty of gardens, explore local landmarks, starting with the gates of neighborhood Michael Jordan estate. The stylish design and rich amenity list will leave you in awe. ✔ Two-Acre Estate ✔ 6 Comfy BRs ✔ Multiple Living Areas ✔ Full Kitchen ✔ Backyard (Pool, Lounges, BBQ) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

Mar 31 – Apr 7

R21,286 ZAR per night

Home in Round Lake Beach

4.99 out of 5 average rating, 102 reviews

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Apr 20 – 25

R3,493 ZAR per night

Apartment in Highland Park

5.0 out of 5 average rating, 42 reviews

Stunning & Stylish Downtown Studio - Highland Park

Experience the charm of downtown Highland Park, IL, in our newly-remodeled, stylish studio apartment, steps away from the metra train! Our space boasts a modern design, two large skylights that flood the area with natural light, and a comfort you'll remember. Discover local shops, eateries, and galleries at your doorstep, the many shorelines and beaches , and retreat to a space that feels like home yet whispers luxury and comfort. Your Highland Park adventure starts here.

Sep 22 – 29

R2,426 ZAR per night

Guest suite in Zion

4.89 out of 5 average rating, 142 reviews

Non-smoking, attached mother-in-law suite.

30 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour to O’Hare Airport and downtown Chicago. 1 hour to Milwaukee 25 minutes to Six Flags and Great Wolf Lodge. Safe and quiet neighborhood with plenty of wildlife right in the back yard. This Mother in Law suite has tons of natural light. For nature lover’s this unit is close to the beach and there are walking trails nearby. Small children maybe heard from 7AM to 7PM.

Jul 21 – 28

R1,781 ZAR per night

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 294 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

Nov 11 – 18

R1,837 ZAR per night

Apartment in Winthrop Harbor

4.94 out of 5 average rating, 228 reviews

Love my guests! Homey Elegant & Lake Michigan!

Large, Cozy, suite w sweet kitchenette for “portable” meals; full-size refrigerator/ freezer; a writing desk for work. Many little ( in case you forgot) items to keep you comfy. This is a quiet town on the gorgeous Lake Michigan. Near: 6 Flags, Great Lakes Navy Base; Cancer Treatment Centers of America & the city Chicago via the Metra in town. Convenient & Quiet. I have 3 dogs. They are kind, outgoing and will want to meet you.

Oct 24 – 31

R1,553 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Highwood vacation rentals

Free parking on premises

Air conditioning

Stay near Highwood's top sights

Miramar Bistro7 locals recommend

Buffo's5 locals recommend

Tala Coffee Roasters - Highwood Cafe3 locals recommend

Disotto3 locals recommend

La Plancha Loca3 locals recommend

Del Rio Restaurant4 locals recommend

Other great vacation rentals in Highwood

Cottage in Highland Park

4.96 out of 5 average rating, 48 reviews

Re-imagined 1880s cottage by Highwood, Metra, Lake

Sep 24 – Oct 1

R5,315 ZAR per night

Guesthouse in Lake Forest

4.95 out of 5 average rating, 97 reviews

The Green Door - safe and calm with walkability

Nov 23 – 30

R1,860 ZAR per night

Guesthouse in Lake Forest

4.88 out of 5 average rating, 81 reviews

Adorable Carriage House East Lake Forest

Sep 21 – 28

R5,227 ZAR per night

Apartment in Libertyville

4.9 out of 5 average rating, 89 reviews

131 East Park Ave. #308

Oct 16 – 23

R1,765 ZAR per night

Apartment in Highland Park

5.0 out of 5 average rating, 12 reviews

Full Apartment green oasis in law suite

Jan 17 – 24

R3,394 ZAR per night

Home in Wilmette

4.98 out of 5 average rating, 92 reviews

Unique porcelain-enamel paneled "Lustron" home

Oct 2 – 9

R3,193 ZAR per night

Home in Lake Forest

5.0 out of 5 average rating, 7 reviews

Parkside Cottage Near the Train

Jan 28 – Feb 4

R3,297 ZAR per night

Home in Northbrook

5.0 out of 5 average rating, 18 reviews

Northbrook Retreat with Ample Outdoor Space

Sep 10 – 17

R6,472 ZAR per night

Destinations to explore