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Vacation rentals in Highland Park

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Top-rated vacation rentals in Highland Park

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

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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.

Dec. 10 – 17

$758 CAD per night

Guest favourite

Home in Highland Park

4.98 out of 5 average rating, 53 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

Nov. 1 – 8

$240 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.

Jun. 12 – 19

$223 CAD per night

Guest favourite

Guesthouse in Evanston

4.98 out of 5 average rating, 199 reviews

Cottage in a Garden

Enjoy the serenity of our secret garden from your private guest house. Enjoy privacy on the covered sun porch. Watch butterflies float by in the pollinator garden. Listen to evening quiet on the patio overlooking the garden. Spin some records from the eclectic collection. Stroll the leafy neighborhood. Stop for a beer at award-winning Temperance Brewery. 5 minute walk to Divvy bike station gives you access to all of Chicago and CTA/Metra train. Short ride to lakefront, Northwestern, downtown.

Mar. 5 – 12

$243 CAD per night

Guest favourite

Apartment in Arlington Heights

4.99 out of 5 average rating, 112 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.

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.

Aug. 15 – 22

$303 CAD per night

Guest favourite

Guest suite in Riverwoods

4.95 out of 5 average rating, 300 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.

Apr. 27 – May 4

$215 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

Forget your worries in this spacious 1 bedroom, 1 bath apartment. Large windows & great natural light. There are new Curtains in the Living Room. Designated Parking on site in long driveway. Features full kitchen with full sized stainless steel appliances, private stackable washer and dryer machines & beautiful tile throughout. Walkable neighborhood - Starbucks, parks, restaurants, dry cleaners & Jewel Grocery Store all 7 minutes walking from apartment. Whole Foods & Target 7 minute drive.

Oct. 15 – 22

$261 CAD per night

Apartment in Highland Park

5.0 out of 5 average rating, 37 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.

Jul. 8 – 15

$229 CAD per night

Guest favourite

Guest suite in Zion

4.9 out of 5 average rating, 135 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 7 – 14

$117 CAD per night

Guest favourite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 290 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.

Jan. 2 – 9

$150 CAD per night

Guest favourite

Apartment in Skokie

4.91 out of 5 average rating, 529 reviews

Cozy Garden Unit in Quiet Neighborhood

A cozy garden unit in the heart of skokie, off of a quiet residential street with plenty of street parking. Just a mile away from the Skokie-Dempster Yellow line train that leads to downtown Chicago, and within a mile from Old Orchard Mall and plenty of great eateries such as: Chick-fil-A, Portillo's, Culver's, Oberwies, Kaufman's Bagel, and more. 15 minutes away from Evanston and the Beautiful Lake Michigan shoreline!

Feb. 23 – Mar. 2

$197 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

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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

Guesthouse in Lake Forest

4.95 out of 5 average rating, 95 reviews

The Green Door - safe and calm with walkability

Mar. 16 – 23

$160 CAD per night

Guest favourite

Cottage in Highland Park

4.96 out of 5 average rating, 46 reviews

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

Sep. 3 – 10

$424 CAD per night

Guest favourite

Home in Northbrook

5.0 out of 5 average rating, 14 reviews

Northbrook Retreat with Ample Outdoor Space

Sep. 23 – 30

$467 CAD per night

Guest favourite

Home in Highland Park

4.85 out of 5 average rating, 41 reviews

A Wonderful Getaway Home on the North Shore!

Oct. 23 – 30

$350 CAD per night

Guest favourite

Home in Wilmette

4.98 out of 5 average rating, 91 reviews

Unique porcelain-enamel paneled "Lustron" home

Oct. 1 – 8

$255 CAD per night

Home in Highland Park

4.88 out of 5 average rating, 8 reviews

The Sunset Manor - Luxe Mansion for Serene retreat

Mar. 16 – 23

$1,380 CAD per night

Home in Lake Forest

5.0 out of 5 average rating, 5 reviews

Parkside Cottage Near the Train

Nov. 17 – 24

$259 CAD per night

Guest favourite

Cottage in Libertyville

5.0 out of 5 average rating, 23 reviews

Woodland Guest House-Vintage Libertyville Chicago

Sep. 15 – 22

$121 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

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