Holiday rentals in Green Oaks

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Top-rated holiday rentals in Green Oaks

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

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Top guest favourite
Guest suite in Zion
4.91 out of 5 average rating, 239 reviews

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.

Top guest favourite
A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.
Guest suite in Riverwoods
4.95 out of 5 average rating, 444 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.

Top guest favourite
A spacious living room is featured with a comfortable sectional sofa, accented by several pillows. A coffee table is centered on a soft area rug, while large windows allow natural light to illuminate the space. Potted plants add a touch of greenery to the decor.
Flat in Highland Park
5 out of 5 average rating, 59 reviews

Full Apartment green oasis in law suite

Beautiful & spacious 1 bedroom, 1 bath in law apartment. New windows with green views. Fragrance free home. There are Curtains in the living room & kitchen. Designated Parking onsite. Full kitchen full sized stainless 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. NO PARTIES.

Guest favourite
A comfortable living area is designed with a gray sofa and a black coffee table, complemented by a dining table. A work desk is positioned near large windows, allowing natural light. A ceiling fan is visible, and a flat-screen TV is mounted on the wall.
Flat in Libertyville
4.88 out of 5 average rating, 33 reviews

305

Kick back and relax in this calm, stylish space. This peaceful, quiet apartment is walking distance to beautiful downtown Libertyville. The building is very nicely maintained with an elevator. Located 7 miles from Great Lakes Naval Base and 35 miles from downtown Chicago. The unit is very clean with all brand new furnishings and appliances including HD tv's in both the living room and bedroom. Free ample parking. On-site laundry one floor down. Fast wifi with a dedicated work space.

Superhost
Flat in Highland Park
5 out of 5 average rating, 3 reviews

Cozy Modern Studio near Ravinia w/Free Parking

Experience Highland Park charm in this luminous studio retreat. Newly renovated with sleek modern touches and warm accents, it’s perfect for couples or concert-goers. Enjoy abundant skylight, a plush queen bed, and a spotless bath stocked with essentials. Just steps from cafés, boutiques, and Ravinia Festival, and minutes from Lake Michigan. Whether you’re exploring or unwinding, this elegant hideaway blends comfort, convenience, and timeless style in the heart of downtown Highland Park.

Guest favourite
A cozy outdoor patio area features a round table with four chairs, complemented by a large umbrella for shade. A chaise lounge rests beside the table, all set on a paved surface surrounded by greenery and a wooden fence for privacy.
Home in Lake Forest
4.86 out of 5 average rating, 42 reviews

Parkside Cottage Near the Train

There's a special price for the next 2 months! Check it out! This special place is close to everything, making it easy to plan your visit. The property is nextdoor to South Park with tennis, pickelball, baseball and basketball courts. The bike path to uptown is directly behind the house. It does back up to the train you can take to downtown Chicago, just 30 minutes away. 1 Mile from uptown Lake Forest. It has a unique charm having been built in 1920. There's only one toilet.

Top guest favourite
The living area features a spacious sectional sofa and a modern armchair positioned around a low coffee table. Large windows provide natural light and a view of the lush green outside. Wall art adds visual interest to the room, complemented by warm wooden flooring.
Home in Waukegan
4.94 out of 5 average rating, 104 reviews

The Victory Park Ranch - West

We are excited to welcome you to this comfortable and newly renovated modern house, in the perfect location if you're visiting Northern Illinois/Chicago. Come see why Waukegan is nicknamed "Green Town" and is home to some of the finest parks, ravines, and walking trails. With an incredible sandy beach, lakefront, galleries, breweries, restaurants, and more, it is definitely a place to check out! We are very close to Six Flags, Great Lakes Naval Base, and The Genesee Theatre too!

Top guest favourite
A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.
Home in Round Lake Beach
4.99 out of 5 average rating, 177 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!

Guest favourite
A cozy bedroom features a black metal bed frame adorned with soft pillows in pink and green hues. Textured white bedding is spread across the bed. Natural light filters through the large windows, complemented by light-colored curtains, and a nightstand sits beside the bed.
Guest house in Lake Forest
4.81 out of 5 average rating, 120 reviews

Designer's Dream in the North Shore!

Welcome to the newly designed cottage at Longmeadow. A tranquil escape from the city hustle of Downtown Chicago. Enjoy the serene setting while close proximity to town amenities, public transit and beautiful trails and parks. A cozy retreat in the wintertime to snuggle up with a great book and hot cocoa. It's also a perfect summer cottage for adventurers looking to take advantage of the beautiful landscape ! Check us out on: Instagram! longmeadowcottage

Guest favourite
A bright living area is showcased, featuring a gray sectional sofa and a minimalist coffee table. Natural light enters through two large windows, with a round mirror reflecting the space. A floor lamp stands beside the sofa, adding soft illumination to the neutral-toned carpet.
Flat in Mundelein
5 out of 5 average rating, 6 reviews

The Modern Rooftop Retreat

Experience a unique rooftop escape in downtown Mundelein! Enjoy the entire upper floor to yourself, featuring a spacious and bright interior with direct access to a relaxing rooftop deck. Steps from Area Coffee, restaurants, and local events like summer concerts, farmers markets, and community festivals, this private retreat blends comfort, convenience, and the lively downtown vibe. Perfect for weekends, work trips, or exploring the area.

Top guest favourite
A spacious and comfortable living area is showcased, featuring a large sectional sofa with decorative pillows and a cozy throw. A coffee table, holding magazines and a candle, complements the soft brown carpet. The kitchenette area, equipped with a full-sized refrigerator, is visible in the background.
Flat in Winthrop Harbor
4.94 out of 5 average rating, 320 reviews

Your best choice* Cozy, spacious, comfortable, lg

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.

Top guest favourite
A spacious living area features modern furniture, including a leather sofa and armchairs arranged around a coffee table. A dining table with blue chairs is visible, complemented by large windows allowing natural light. The room has a warm and neutral color palette.
Loft in Libertyville
4.94 out of 5 average rating, 123 reviews

Historic Downtown Libertyville Loft

Enjoy a stylish experience at this centrally-located 1600 square foot place. Located in the heart of Downtown Libertyville, half way between Chicago and Milwaukee. Close to Six Flags, Great Lakes Navy Base, Lake Michigan beaches, forest preserves, train station and the Chain of Lakes. Downtown Libertyville is a trendy town offering several restaurants, shops and fun events. Book one of the only units truly Downtown Libertyville.

Popular amenities for Green Oaks holiday rentals

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