Holiday houses in Indian Head Park

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Top-rated holiday rentals in Indian Head Park

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Guest favourite

Condo in Westchester

4.97 out of 5 average rating, 37 reviews

Modern Oasis – Minutes from O’Hare

Relax in simplicity in this peaceful, centrally located garden apartment. Were just 15 minutes from O'Hare Airport, and exciting Rosemont Center, Outlet mall and Casino, 20 minutes from Downtown Chicago, 10 minutes from the fabulous outdoor Oak Brook Mall with tons of shopping, entertainment, and restaurants. This apartment offers everything you need in a serene setting. With easy access to 3 major expressways I-290, I-294 and I-88. It’s in a great quiet neighborhood with friendly neighbors.

Guest favourite

A well-lit dining area features a rectangular table accompanied by four wooden chairs and a bench. Natural light filters through large windows, illuminating the space. A small potted plant is centered on the table, enhancing the clean and modern decor.

Home in Westmont

4.91 out of 5 average rating, 33 reviews

Cute & Cozy Westmont, IL House Near the Best Areas

Beautiful 2 bedroom 1 bath house with a 2 car garage, private driveway and plenty of parking. With a nice back yard in one of Westmont's prime location close to great restaurants, shopping areas, easy access to expressways and airports in a great quiet neighborhood. Fully furnished with high-speed internet Wifi and stocked with essentials to make your stay comfortable. Near Morton Arboretum, Metra Station, Yorktown Center, upscale Oakbrook Center and a short commute to downtown Chicago.

Guest favourite

The exterior of a single-story home is framed by lush green grass and dark mulch landscaping. A welcoming pathway leads to the front door, adorned with a seasonal wreath. A large tree provides shade, and a white fence marks the boundary of the yard.

Home in Naperville

4.87 out of 5 average rating, 162 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Top Guest favourite

A living area showcases a wooden entertainment center with a TV, flanked by a decorative console table and two lamps. The space features hardwood floors and a neutral color palette, complemented by a circular wall mirror. A staircase in the background leads to the upper level.

Condo in Clarendon Hills

5 out of 5 average rating, 111 reviews

Apartment in Clarendon Hills.

Newly renovated Suite in multi family home in Clarendon Hills. Main level: fully equipped kitchen/island, dining area, living room & family room with fireplace. Upper level: Bedroom 1 - king size bed, walk in closet, private bathroom/shower. Bedroom 2 - queen bed, closet. Bedroom 3 - size bed, closet. Living room has a pull-out sofa bed. Family room with gas fireplace, access to deck/outdoor area. Easy access to restaurants, shopping (Oak Brook Mall minutes away), Metra, O’Hare.

Guest favourite

A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.

Home in Berwyn

4.98 out of 5 average rating, 195 reviews

Retro Modern Bungalow | free parking | fire pit

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 backyard. Enjoy central HVAC, speedy 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 favourite

Double French doors open into a bright, inviting living space. A patterned area rug lays on polished hardwood floors, leading to a cozy seating area with upholstered chairs. Decorative artwork adorns the walls, and soft light filters in through the windows.

Apartment in Oak Park

4.94 out of 5 average rating, 191 reviews

A Quiet Stay While You Are Away Oak Park

Welcome to our cozy and comfortable home located in a quiet neighborhood. Our space is perfect for couples, solo travelers, small families, and long-term stays. This is a beautiful, modernist home located in the Frank Lloyd Wright District Neighborhood, a designated historic district known for its collection of homes designed by the famous architect Frank Lloyd Wright. This district features a collection of some of his iconic designs and is a destination for architecture enthusiasts.

Guest favourite

A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.

Apartment in Aurora

4.98 out of 5 average rating, 227 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 favourite

The kitchen showcases modern stainless steel appliances, including a refrigerator and microwave. Granite countertops are paired with sleek cabinetry. A small island with two stools occupies the space, while a view of the living area is visible in the foreground.

Apartment in Chicago

4.92 out of 5 average rating, 207 reviews

Cozy Hidden Gem Near Downtown+Train+Dining+Parking

Experience one of the best neighborhoods in Chicago in this Hidden City Gem, 2BR/1bath apartment. Perfect for couples, families, or small groups. Centrally located, just minutes to downtown, CTA/L Pink Line train is one block away, Free WiFi, permit parking, cable, in-unit front load washer/dryer, highways nearby. Explore the vibrant community, art/murals, delicious food, and cultural venues. Book now for a comfortable and memorable stay in the Heart of Chicago Pilsen Neighborhood.

Top Guest favourite

A sitting room features a beige sofa and a cream-colored armchair, positioned near a wooden desk. Two lamps provide soft lighting, while several framed photographs and artwork adorn the walls. Large windows allow natural light to fill the space, complemented by neutral-colored carpeting.

Guest suite in Orland Park

4.97 out of 5 average rating, 113 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.

Top Guest favourite

A polished granite countertop is highlighted, showcasing a vibrant bouquet of pink roses in an elegant vase. Natural light filters through large windows, illuminating a cozy seating area in the background. Decorative greenery adds a touch of warmth to the setting.

Apartment in Burbank

4.98 out of 5 average rating, 276 reviews

New & Modern by Midway Airport

Located 4 miles away from Midway Airport in Chicago, Seat Geek Stadium 4 miles away, 20min to Down Town, 15min to Amphitheatre in Tinley Park 2-Bathrooms 3-Bedrooms one with queen size bed and 2 bedrooms with 4 single beds can accommodate up to 6 people. Two TV's 4K Incl. HBO MAX & NETFLIX & PEACOCK. Whether you're in town on business or for personal reasons our space has been meticulously designed to provide you with the best stay in the area! Digital check-in.

Top Guest favourite

The exterior of the vintage garage apartment is shown, featuring a bright yellow facade with two white garage doors. A large window is positioned above the doors, with greenery surrounding the property, contributing to the charming appearance.

Guesthouse in Villa Park

4.92 out of 5 average rating, 146 reviews

Eclectic Coach House Apartment

Vintage Charmer! 1935 Sears Craftsman Coach House garage apartment. Beautiful safe neighborhood surrounded by historic homes and just steps from the Illinois prairie path, parks, brewery's/bars, restaurants and more! With an eclectic boho chic vibe, featuring full kitchen and on site private washer/dryer. Overlooking an accessible lovely backyard! Close to airports and easy access to public transportation/major highways. Just 30 min from the Chicago Loop!

Guest favourite

The collage showcases various areas of the property, including a modern living space with a wall-mounted TV, a two-story exterior featuring stone details, an outdoor patio area with seating under a pergola, a game room equipped with a ping pong table, and a bathroom with a jacuzzi tub and neatly arranged towels.

Home in Westchester

4.97 out of 5 average rating, 116 reviews

Jacuzzi, King Beds, Easy Access to DT Chicago!

Our 4bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful neighborhood. There is plenty of space for 10 people to sleep comfortably (4 beds), as well as 4 smart TVs, a deck w/ a pergola, built-in grill, & firepit, a large fenced backyard, a game room (w/ ping pong and more), a jacuzzi, an office space, & much more. Great access to City of Chicago by I-290, as it's directly west of Downtown!