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Vacation rentals in Highland Park

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Top-rated vacation rentals in Highland Park

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Home in Highland Park

4.91 out of 5 average rating, 109 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. 7 – 14

$795 CAD per night

Guest favourite

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

Mar. 31 – Apr. 7

$214 CAD per night

Guest favourite

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. 24 – May 1

$212 CAD per night

Guest favourite

Apartment in Arlington Heights

4.99 out of 5 average rating, 115 reviews

Ideal Location in Awesome Heights

Near the heart of downtown Arlington Heights and convenient to O’Hare. You can settle in at this cozy basement apartment with a super comfortable queen bed and all the amenities you’d need. Whether your visit to AH is for business or pleasure, city or suburbs, we look forward to hosting you. The private apartment works great for guests with a car or using public transit. Easy access to Metra station, AH restaurants, Des Plaines Theater, NW Community Hospital & Schaumburg Convention Center.

May 5 – 10

$207 CAD per night

Guest favourite

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.

Dec. 25 – Jan. 1

$302 CAD per night

Guest favourite

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

$240 CAD per night

Guest favourite

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!

Nov. 14 – 21

$1,542 CAD per night

Guest favourite

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!

Dec. 8 – 13

$288 CAD 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.

Oct. 2 – 9

$211 CAD per night

Guest favourite

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.

May 16 – 23

$116 CAD per night

Guest favourite

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.

Feb. 19 – 26

$149 CAD per night

Guest favourite

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. 6 – 13

$111 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Houses

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Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Highland Park vacation rentals

Free parking on premises

Air conditioning

Stay near Highland Park's top sights

Whole Foods Market5 locals recommend

Lake-Cook /Chicago Botanic Garden station14 locals recommend

Jewel-Osco9 locals recommend

Ravinia Festival West Lot33 locals recommend

Rosewood Beach7 locals recommend

Miramar Bistro7 locals recommend

Other great vacation rentals in Highland Park

Guest favourite

Home in Highland Park

4.98 out of 5 average rating, 59 reviews

Charming Ranch-Style Cottage

Sep. 14 – 21

$253 CAD per night

Guest favourite

Cottage in Highland Park

4.96 out of 5 average rating, 48 reviews

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

Oct. 23 – 30

$420 CAD per night

Guest favourite

Guesthouse in Lake Forest

4.95 out of 5 average rating, 96 reviews

The Green Door - safe and calm with walkability

Sep. 18 – 25

$159 CAD per night

Guest favourite

Apartment in Highland Park

5.0 out of 5 average rating, 12 reviews

Full Apartment green oasis in law suite

Sep. 16 – 23

$259 CAD per night

Guest favourite

Home in Wilmette

4.98 out of 5 average rating, 92 reviews

Unique porcelain-enamel paneled "Lustron" home

Sep. 22 – 29

$252 CAD per night

Guest favourite

Apartment in Libertyville

4.9 out of 5 average rating, 89 reviews

131 East Park Ave. #308

Sep. 7 – 14

$153 CAD per night

Guest favourite

Home in Northbrook

5.0 out of 5 average rating, 17 reviews

Northbrook Retreat with Ample Outdoor Space

Sep. 10 – 17

$506 CAD per night

Guest favourite

Home in Highland Park

4.86 out of 5 average rating, 43 reviews

A Wonderful Getaway Home on the North Shore!

Apr. 22 – 29

$470 CAD per night

Quick stats about vacation rentals in Highland Park

Total rentals
50 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.8K reviews
Nightly prices starting at
$41 CAD before taxes and fees

Destinations to explore