
Vacation rentals with a patio in Highland Park
Find and book unique accommodations with an outdoor patio on Airbnb
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.

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (1 Full, 1Queen) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard with exceptional landscaping. The property has a car port in back which allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! NO CHORES! Please reach out with any questions you may have before booking Hot tub 5-6 Person Spa

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.

Charming Riverfront Stay | Heart of Downtown
Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

WONDERFUL WICKER PARK 2BD/2BA w/ patios +parking
Escape into this spacious condo in a bustling top-notch, Chicago neighborhood! Guests love this home because: - Surrounded by top-notch restaurants/retail - Close to all popular attractions that make Chicago so great - Luxurious, newly-renovated interior filled with natural light - Open-floor plan for entertaining! - 2 private walk-out patios! - Fast WiFi (600 mbps) - Master en-suite w/ separate walk-out patio - Designated parking spot! - Steps away from blue line Damen station (800 feet)

Nonsmoke, No Cleaning Fees, No Long Chore Lists.
25 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour 40 minutes to O’Hare Airport and downtown Chicago. 40 minutes to Milwaukee Airport 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 8PM.

Private hot tub - King bed suite - Free parking
Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Cozy & Bright Townhome near O’hare -Self Check In-
Escape into this Montclare Masterpiece! Be one of the first guests to enjoy our revitalized, fully-stocked home with attached deck. This 3-level home comes with a spacious, light-flooded living area with attached open kitchen w/ SS appliances, granite countertops/ backsplash, and accent lighting - perfect for larger groups. On the third level you'll find 2 elegant bedrooms with ample closet space, updated full bathroom, and in unit washer and dryer provide all the essentials and more!

White House, 5 Beds
Completely updated and fully furnished single family ranch home with lots of space less than 10 minutes away from downtown Arlington Heights. The home is equipped with 3 Queen beds, 1 full bed, a sofa bed, a 65 inch tv in the living room with a sound bar and subwoofer, 43" tv's in 3 of the bedrooms, and a 32' tv in the fourth bedroom. The large deck in the back is great for entertaining. The home has a pool table which is great for entertaining as well. Book your stay with us today!

NEW~2 Spa Baths~Game Room~Prime Area~Big Yard~
✅Updated Home- RARE 1/3+ Acre Fenced Yard 🏠 ✅Huge Vaulted Ceiling Family Room 🛋️ ✅2 Full Updated Bathrooms on Main Level🪥🛀 ✅Game Room w/Air Hockey & Basketball🏒🏀 ✅Dining Room Seats 10🪑 🍽️ ✅Quiet Neighborhood + Convenient Location🏘️ ✅Open Kitchen Floorplan 🍳👨🍳 ✅Outdoor Seating🌳 ✅EZ Driveway Parking for 4 Cars🚗🏎️ ✅Close to O’Hare Airport(8 Min)🛫 ✅Close to Stephens Convention Center(12 Min)👨👩👧👧 ✅Close to Allstate Arena(7 Min)🎤 ✅Close to River’s Casino(8 Min)♥️🎰

TheGlassCabin @ HackmatackRetreat
The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

Clean & Cozy, Near, Train w/ Parking, Sleeps 4
Escape to an enchanting garden studio nestled in Oak Park's famous historic district. Discover our private urban farm with full gardens and 6 cheerful hens. Stroll to charming stores, cafes, and restaurants, or hop the nearby "L" for effortless Chicago adventures. Free parking, easy airport access. This serene, non-smoking studio with a kitchenette requires no check-out chores. No parties, 4 guests max. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

Victorian House in Heart of Rogers Park
Newly restored Victorian house giving you a touch of Chicago's history with modern comfort. Feel at home away from home with fully equipped kitchen, entire house, and outdoor spaces with beautifully landscaped garden for lounging, grilling, and chilling. Large screen TV in living room and TVs in each bedroom. Fast Wi-Fi throughout the house. Walking distance to public transit, restaurants, bars, beach and shopping. Designated parking. #TheCatalpa
Popular amenities for Highland Park accommodations with an outdoor patio
Apartment rentals with a patio

Andersonville's Secret Garden: 2 beds, 1 bath

Sunny 1 bedroom apartment 1 block from restaurants

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

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

Cozy guest studio, great for couples!

Vibrant & Chic Apt On Quiet St in Andersonville

Home in Forest Park downstairs.

Spacious 3 bdrm apt. near NU + Chicago + lake.
House rentals with an outdoor patio

Casa 22 | Luxury Modern House for 6 | 3 Bed,2 Bath

Designer Furnished + Game Room | LCP Collection

Lake House Walk to Train-Chicago

Luxury Lake Home

1/2 Acre Retreat: 100" TV, Open layout | Navy Base

THE VAIL /hot tub/ev charger/fire pit/grill/garage

*New* Luxury Wrigley Penthouse, Free Parking

Peaceful Stay North Shore Escape | 8 Beds (2 King)
Condo rentals with a patio

Lovely top floor 2BR/2BA, steps from everything!

- King Bed - Massive Yard - Fully-Equipped Condo -

Downtown Chicago - Spa Bath, Patio, 3 blocks to L

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

Can't Beat This 2min Walk to Wrigley!

Spacious 4 Bedroom Condo

Wicker Park/Bucktown condo with large balcony

Updated Designer Duplex In Fulton Market W/parking
When is the best time to visit Highland Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $305 CAD | $295 CAD | $388 CAD | $386 CAD | $419 CAD | $395 CAD | $402 CAD | $445 CAD | $422 CAD | $303 CAD | $351 CAD | $351 CAD |
| Avg. temp | -4 °C | -2 °C | 4 °C | 10 °C | 16 °C | 21 °C | 24 °C | 23 °C | 19 °C | 12 °C | 5 °C | -1 °C |
Quick stats about vacation rentals with a patio in Highland Park

Total vacation rentals
Explore 30 vacation rentals in Highland Park

Nightly prices starting at
Highland Park vacation rentals start at $70 CAD per night before taxes and fees

Verified guest reviews
Over 1,560 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Highland Park vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Highland Park rentals

4.8 Average rating
Highland Park stays are highly rated by guests—averaging 4.8 out of 5!
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- Rentals with a patio Lake County
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- Rentals with a patio United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Alpine Valley Resort
- Oak Street Beach
- The Field Museum
- Garfield Park Conservatory
- Wicker Park
- Lincoln Park Zoo
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- The Beverly Country Club
- Illinois Beach State Park
- The 606
- Wilmot Mountain Ski Resort




