Holiday rentals in Clarendon Hills

4.89 out of 5 average rating, 194 reviews

A spacious artist loft features a living area with hardwood floors and large windows allowing natural light. A leather sofa is positioned in the center, with stylish chairs nearby. The open kitchen is visible in the background, along with a modern dining space under soft lighting.

Loft in Brookfield

1920s fully updated unique open artist loft space

True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

4.96 out of 5 average rating, 45 reviews

King beds, firepit, lake view

We may take a refundable deposit. We must say this because our direct booking site is linked. A lovely place on the lake in summer we rent entire house. This is a home that is split into a duplex. One side we have 3 bedrooms 2 baths. The other side is 1 bedroom and 1 bath. Both sides have separate entrances and decks. Enjoy the beautiful view while staying. You have access to entire house and yard except garage with this listing. This listing is for renting both sides. They do not connect.

4.97 out of 5 average rating, 61 reviews

A spacious living room features a large sectional sofa adorned with various cushions, complemented by a cozy throw. A sleek flat-screen television is mounted above a natural stone fireplace. Large windows allow natural light to fill the room, enhancing the inviting atmosphere.

Home in Lombard

Spacious Home in Chicago Suburbs

Enjoy your stay in Chicagoland in this gorgeous, newly updated home. After a full day of sightseeing in the Windy City or hitting the local shops and attractions, this is a restful homebase to return to. The spacious fenced-in backyard and patio, a comfortable and tastefully furnished basement, and the full kitchen with amenities provide the perfect environment to unwind. You’ll find plenty of seating, sleeping accommodations for nearly a dozen, and an open layout that fosters connection.

Apartment in Clarendon Hills

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.

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.

5.0 out of 5 average rating, 138 reviews

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.

4.89 out of 5 average rating, 63 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.

4.84 out of 5 average rating, 25 reviews

Home in La Grange

Elegant Escape in Top Location

This fully equipped home is just minutes from Burr Ridge Village Center with easy access to restaurants, bars, shopping, and local breweries. Outdoor enthusiasts will love the proximity to parks, golf courses, and scenic trails, perfect for hiking, biking, or a leisurely stroll. For those wanting to explore further, downtown Chicago is easily reachable via nearby bus or train options, offering the best of both worlds—peaceful suburban retreat with vibrant city life just a short trip away.

Superhost

An entertaining area features a slate pool table positioned on polished wooden flooring. Natural light fills the space through large windows, illuminating a cozy seating option along the wall. A staircase is visible in the background, leading to the upper level.

Home in Downers Grove

Premium 5BR Home • Great for Extended Visits

Experience unmatched comfort and upscale living in this stunning 5-bedroom, 3.5-bath luxury retreat in Downers Grove. Perfect for extended stays, relocations, insurance housing, business trips, or large family getaways, this home combines spacious living with elegant design. With room for up to 12 guests, premium amenities, a fully equipped kitchen, multiple living and entertainment areas, and an expansive backyard, this home is designed to make long stays feel effortless and indulgent.

4.81 out of 5 average rating, 54 reviews

4.83 out of 5 average rating, 40 reviews

Home in Downers Grove

Springside Retreat: Charming Chicago Suburb

Enjoy a clean, comfortable stay in a quiet suburban home designed for real living—not just sleeping. Ideal for families, professionals, and longer stays, this well-maintained home offers space, privacy, and a calm residential setting away from city noise. Inside, you’ll find generous living areas, a practical layout, and thoughtful furnishings that make it easy to settle in. Whether you’re working remotely, visiting family, or staying longer term, the home is set up to be comfortable.

4.84 out of 5 average rating, 149 reviews

“Aunt Betty’s Cottage” sleeps up to 6 Large yard

Perfect cottage living sleeps up 6 adults c Westmont. Decor is vintage chic with a focus on retro arts and collectibles. Cozy blankets and whimsical art adorn the walls. Perfect for folks who love cute quaint CLEAN and comfy not Kondo! A place to call home where the barn door closes off the Living room. A dinner for 6 in the quaint dining area. Laundry room in the home. New fenced yard out door furniture. Beyond pet friendly we have many accessories for Dogs.

4.99 out of 5 average rating, 108 reviews

A single-story brick home with a well-maintained front yard features green shrubs and a neat pathway leading to the entrance. Large windows allow natural light to illuminate the interior, while a tree provides shade near the entrance.

Home in Brookfield

Cozy Home in Brookfield

Discover tranquility just minutes from the busy city life! Nestled in the heart of Brookfield, IL, our charming home offers the perfect blend of suburban serenity and urban convenience. Just an 8-minute walk from the train station, you'll find easy access to downtown Chicago while enjoying the peaceful atmosphere of our neighborhood. Max 4 overnight guests. No parties or events. Pets allowed (no exotic pets or animals with a bite history).

4.92 out of 5 average rating, 26 reviews

Sleeps 10 • Everyone Stays Together Pets too

📍20 Mi to McCormick • 18 Mi to Rosemont 💼 10 min to Oak Brook Hills & conference venues. 🏆 Sleeps 10 — perfect for teams & groups. 🛋️ 4BR home with workspace & fast WiFi . 🧺 In-unit washer/dryer for gear & wardrobe. 🍳 Full kitchen, dining for 6. 🎱 Fuseball table + board games for downtime . 🚗 Free parking for vans & carpools . 🐾 Pet-friendly. 🚆 5 min drive to Metra, direct to Chicago. 🏕️ Your team's basecamp near it all!