Vacation rentals in Hickory Hills

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Top-rated vacation rentals in Hickory Hills

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

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Guest favorite

A well-lit living area features a mix of modern furnishings, including a comfortable sectional sofa and a coffee table. A large potted plant adds a touch of greenery. Natural light enters through a window, while dark curtains provide contrast. An entertainment center is visible, containing a game console.

Home in Oak Lawn

5 out of 5 average rating, 6 reviews

Stylish Convenient House Peaceful Retreat 4BR 2BTH

Welcome to our cozy home! Located just 18 mile about 30 minutes from the vibrant downtown area.and midway airport 15 minutes our bright and spacious 4 bedroom and 2 bathroom newly remoder,offers a perfect base for exploring the area. Enjoy a comfortable stay with a fully equipped kitchen, a cozy living area. We're conveniently located near popular shopping,mall,restaurants, parks, and the Explore the local shops…Book your stay now and Enjoy a stylish experience at this centrally-located place.

Top guest favorite

Home in Berwyn

4.99 out of 5 average rating, 146 reviews

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at Retro Modern Bungalow—the perfect pad for up to 4 friends. Featuring two spacious bedrooms, each with a king bed and luxury linens, a propane fire pit and a fully fenced [pup-friendly] back yard. Enjoy central HVAC, hi-speed WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Guest favorite

An aerial view captures a vast expanse of snowy landscapes interspersed with patches of dense forests and winding waterways. The aircraft wing extends prominently into the frame, showcasing the engine below and the clear blue sky above, creating a serene and expansive atmosphere.

Apartment in Lemont

4.91 out of 5 average rating, 68 reviews

Burr Oak

Nestled in the Palos Forest Preserve with access to many miles of hiking and biking trails . Spacious one bedroom basement apartment with private entrance. 6 minutes to The Forge, 7 minutes to Target, 8 minutes to downtown Lemont restaurants. 4 minutes to Little Red Schoolhouse, 7 minutes to Burr Ridge shopping and dining. 22 minutes to Midway 32 minutes to O'Hare. Half hour to the Loop. 20 minutes from Ikea and Bass Pro. Very quiet cabin like setting. Ask about our extended stay discounts.

Top guest favorite

A lively indoor space is filled with patrons enjoying themselves. Exposed brick walls and wooden beams contribute to the ambiance, while various seating arrangements create a welcoming atmosphere. Dim lighting highlights a large television, with a vibrant bar area visible in the foreground.

Guest suite in Brookfield

5 out of 5 average rating, 102 reviews

Charming Chicago suburb! 1 bedroom apartment.

Enjoy your stay just west of Chicago in our 1880 updated 1st floor of a 2 flat. You get a one bedroom apartment with queen bed, private kitchen and bath, separate office for work, plus 2 porches for you to enjoy. Brookfield is a charming village with unique restaurants, bars, salon and day spa, coffee shops, library and the train to Chicago--all within a 5 minute walk. We want you to feel at home; but before you book understand that you may not smoke ANYTHING in the unit or on the property.

Top guest favorite

The exterior of the home features light-colored siding and red shutters, complemented by neatly trimmed shrubs. A stone pathway leads to a white front door, flanked by large windows that allow for ample natural light. Lush green grass surrounds the entrance.

Guest suite in Geneva

4.99 out of 5 average rating, 659 reviews

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

Guest favorite

A renovated coach house is presented with a light yellow exterior, featuring a welcoming entrance flanked by two windows. Lush greenery frames the yard, while a vibrant flower bed and a basketball hoop enhance the outdoor space. A paved pathway leads to the entrance.

Home in Chicago

4.86 out of 5 average rating, 139 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Superhost

A sturdy wooden shelf displays neatly stacked white towels, emphasizing a clean and organized bathroom space. The backdrop features warm beige walls and a tiled section, creating a balanced and functional design.

Condo in Hickory Hills

4.85 out of 5 average rating, 99 reviews

Convenient Location near ammenities. KING size bed

Walking distance to restaurants, stores etc. 1st floor suite will be your relaxing retreat. King size bed with a 12 inch foam mattress, down pillow/comforter set, blackout curtains will allow you a restful sleep. BR is equipped with 2 side tables, 2 dimmable touch control table lamps with 2 USB Ports. Bath offers a tub, vanity & open shelving. LR features faux leather sofa, coffee table w/the lift-top & 70” streaming TV. LR opens up to an eat in kitchen equipped with standard dine-ware.

Top guest favorite

Apartment in Aurora

4.99 out of 5 average rating, 154 reviews

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Top guest favorite

A sleek keypad entry system is mounted on the doorframe, featuring numerals and a circular keyhole. The brushed metal finish adds a modern touch, while the textured gray wall provides a subtle backdrop.

Guest suite in Orland Park

4.98 out of 5 average rating, 97 reviews

Private Guest Suite 2 Cozy Rooms

Private guest suite with separate entrance. Sitting room, kitchenette, bedroom w/queen bed, private bath, plus twin sofa bed in sitting room. Great alternative to hotel for business trip or visiting the area. Conveniently located in southwest suburbs of Chicago, 40 minutes from downtown by car (non rush hour) or Metra lines a few miles from the house. Set near a golf course and forest preserve, nearby to multiple restaurant and shopping districts less than 10 minutes away.

Guest favorite

An inviting entrance features a dark door flanked by large windows, framed by a small patio. Snow lightly dusts the surrounding plants and seating, which includes two chairs and a table. Potted flowers add a touch of color to the winter scene.

Tiny home in Burr Ridge

4.9 out of 5 average rating, 373 reviews

Less is more! Pet friendly Tiny Home near Chicago!

Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome

Guest favorite

A spacious kitchen features modern white cabinetry, granite countertops, and stainless steel appliances. The room is well-lit with recessed lighting and a pendant light above the sink. A door leads to the adjoining hallway, while large tiles cover the floor for easy maintenance.

Home in Worth

4.87 out of 5 average rating, 134 reviews

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

This beautiful, newly remodeled, spacious, 3 bed 2 bath ranch style home is set back on a large lot. Located close to a major hwy, restaurants and a shopping. Just 15 minute to Midway Airport, 25 mins to O'Hare, and 25 mins to Downtown Chicago. Its a great spot to get to everything! Perfect for families, vacationers, and business travelers. You must be 21 or older to book. You must provide a valid photo of your D.L. or State ID upon request.

Guest favorite

A private jacuzzi is situated under a shaded pergola, with warm ambient lights enhancing the serene atmosphere. A view of an outdoor dining area with a table and chairs is visible through a nearby opening, framed by lush greenery and a tranquil landscape.

Guesthouse in Merrillville

4.92 out of 5 average rating, 110 reviews

Romantic Getaway Guesthouse/ Jacuzzi/Sauna/Pool

Romantic Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse/in-law suite offers ultimate relaxation with a private entrance, spa-like jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.