Vacation rentals with a patio in Highland Park

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Top-rated accommodations with an outdoor patio in Highland Park

Guests agree: these accommodations with an outdoor patio are highly rated for location, cleanliness, and more.

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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. Full kitchen with full sized stainless steel appliances, private stackable washer and dryer machines & beautiful tile throughout. Bring slippers tile can be chilly to touch - if barefoot. Starbucks, parks, restaurants, dry cleaners & Jewel walking distance from apartment. Whole Foods & Target 7 min. drive.

Dec. 8 – 15

$258 CAD per night

Guest favourite

Home in Wilmette

4.98 out of 5 average rating, 92 reviews

Unique porcelain-enamel paneled "Lustron" home

This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

Sep. 23 – 30

$252 CAD per night

Guest favourite

Home in Northbrook

5.0 out of 5 average rating, 16 reviews

Northbrook Retreat with Ample Outdoor Space

Welcome to our sophisticated ranch style home, nestled in the serene, central Chicago neighborhood of Northbrook. This carefully curated home offers a peaceful retreat in a walkable neighborhood with nearby shopping and dining. With its elegant decor, comfortable furnishings, and modern amenities, the home provides a haven of relaxation. Whether you're enjoying a cup of coffee on the private patio or exploring the area, this home provides the perfect backdrop for a memorable vacation experience.

Sep. 10 – 17

$517 CAD per night

Guest favourite

Apartment in Oak Park

4.91 out of 5 average rating, 104 reviews

Lovely, spacious 2bd, 1bath home w/free parking

Bring the whole family to enjoy this great place with lots of comforts and space. Beautifully decorated with reclaimed barn wood throughout the home and a completely remodeled kitchen with cute bistro table to enjoy your coffee. Wonder around this beautiful, quiet Frank Lloyd Wright neighborhood to see beautiful Victorian homes and architect or take a brisk walk to downtown Oak Park before taking in the sites in Downtown Chicago. Whether you stay for a while or a few days, welcome home!

Oct. 1 – 8

$213 CAD per night

Guest favourite

Cottage in Libertyville

5.0 out of 5 average rating, 23 reviews

Woodland Guest House-Vintage Libertyville Chicago

The Woodland Guest House is uniquely located within a forest setting, and on a major road a 10-minute drive to downtown Libertyville and the Chicago train line. The modern apartment suite has four rooms, and was built onto an adjacent 1908 farmhouse. It combines peaceful silence with modern amenities, and is full of character. On three acres of oak savannah and trails, it is a certified Open Lands Property. Come to explore this exciting area, while staying in a charming forest suite!

Oct. 14 – 21

$119 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!

A perfect place to visit the northern highlights of Chicago! 1/4 mile from Ravinia! 1.5 miles from the Botanic Gardens! 30 minutes from Chicago (an hour from Milwaukee). Close to trains, planes and easy automobile access. A two-bedroom gem in the heart of so many wonderful things. Other local places: Northwestern University, Lake Forest, Winnetka, Lake County ... I do have a cat that lives here but he goes with me when I leave. I just wanted to let you know in case you have allergies.

Dec. 9 – 16

$343 CAD per night

Guest favourite

Apartment in Libertyville

4.89 out of 5 average rating, 45 reviews

528 Bungaloo 1 | 1 Bedroom | 1 Bath | Sleeps 2-4

Aug. 26 – Sep. 2

$258 CAD per night

Guest favourite

Home in Round Lake Beach

4.89 out of 5 average rating, 151 reviews

Corner Lakefront Property

This unique place has a style all its own. This corner lake house comes with a huge fenced-in yard, as well as a balcony off of the master bedroom and 2 parking spots. We offer 3 kayaks with life jackets, 1 paddle board, paddle boat and fishing poles, fire pit, outdoor and indoor games. We have 3 bedrooms with beds included, as well as a futon couch a trundle bed and a pull-out couch bed (6 potential beds total). This comes with 2 TVs, fireplace, WiFi, bar, new fridge and more.

Feb. 26 – Mar. 5

$348 CAD per night

Guest favourite

Guest suite in Zion

4.89 out of 5 average rating, 140 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

$120 CAD per night

Guest favourite

Apartment in Evanston

5.0 out of 5 average rating, 37 reviews

South Evanston Apartment - Two Bur Oaks

Charming garden apartment within single family home in friendly neighborhood with free street parking. Clean and comfortable with heated floors. 1.5 miles west of Lake Michigan and a mile from CTA and Metra. Easy access to Northwestern University and Chicago. Dedicated patio and entryway via exterior stairwell. Outdoor stove and wood available for bonfire upon request. Great for working at nearby hospitals and universities and for exploring or commuting to the city.

Feb. 14 – 21

$188 CAD per night

Guest favourite

Apartment in Cicero

4.98 out of 5 average rating, 201 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

Dec. 11 – 18

$196 CAD per night

Guest favourite

Guest suite in Wheaton

4.85 out of 5 average rating, 100 reviews

Cozy Wheaton Home

Cozy lower level apartment close to DT Wheaton & Glen Ellyn, restaurants, coffee shops, and shopping. Only 40 minutes outside of the DT Chicago! Train station is walking distance. You'll have the entire lower level of our home to yourself! You'll be able to enjoy your own private entrance, living space, and parking . There is everything you need, coffee, tea, mini fridge, microwave, and a comfy couch with a Firestick TV!

Feb. 13 – 20

$166 CAD per night