Holiday rentals in Darien

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Top-rated holiday rentals in Darien

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

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Guest favourite

A cozy living area is highlighted by a plush navy sofa adorned with a yellow accent pillow. A light-colored area rug with stripes lies beneath. The room features a decorative painting of trees and a stained glass window, adding character to the inviting space.

Guest suite in Glen Ellyn

4.92 out of 5 average rating, 204 reviews

✽ Charming Cottage ✽ close to College/Town/Station

Charming and cozy single family home fully renovated in a superb location! This house is walking distance to the Chicago metra rail system and Wheaton College, as well as a 6 minute drive to both downtown Wheaton and downtown Glen Ellyn! Relax and unwind in this darling home that we fell in love with! The health and safety of our guests is important to us. Due to COVID-19 we are taking extra care to professionally disinfect frequently and completely between every reservation UP TO CDC STANDARDS

Guest favourite

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

4.91 out of 5 average rating, 154 reviews

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

Guest favourite

A fenced backyard features a circular arrangement of wooden lounge chairs centered around a propane fire pit, creating a cozy gathering space. Twinkling string lights hang above, illuminating a bistro table with two blue chairs. Lush green grass surrounds the stone patio area.

Home in Berwyn

4.98 out of 5 average rating, 196 reviews

RetroModern Bungalow | free parking | pet friendly

Experience the city in style at Retro Modern Bungalow, the perfect pad for up to four 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

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, 163 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.

Apartment in Clarendon Hills

5 out of 5 average rating, 115 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.

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

4.83 out of 5 average rating, 46 reviews

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.

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.

Flat in Aurora

4.98 out of 5 average rating, 229 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.

Superhost

A modern dining area features a round wooden table surrounded by four woven chairs. Bright overhead lighting illuminates the space, which connects to a sleek kitchen with stainless steel appliances. Open layout enhances the airy feel, with a cozy seating area visible in the background.

Home in Lisle

4.86 out of 5 average rating, 66 reviews

Captivating Home near Naperville

A captivating, newly renovated 3 bedroom / 2 bathroom with fully furnished basement. Clean finishes and modern amenities create the perfect, relaxed space for you and your group. Minutes from downtown Naperville! Walk to downtown Lisle for restaurants, shopping, outdoor events, walk to Lisle train station, Lisle Community Park with walking paths, outdoor summer concerts, playing fields, walk to Prairie Walk Pond with weekly French Market May thru Oct, walk to Sea Lion Aquatic Park.

Guest favourite

A cozy bedroom features a spacious bed dressed in floral bedding, complemented by pastel pillows. Two nightstands frame the bed, and a light-colored rug covers the floor, adding warmth to the neutral walls. Soft lighting is provided by recessed ceiling fixtures, enhancing the serene ambiance.

Home in Woodridge

4.86 out of 5 average rating, 66 reviews

Private Apartment • Ground Floor • Free Parking

Cozy 1-Bedroom Apartment on the Ground Floor in a quiet Woodridge neighborhood + Free parking for 2 cars. Perfect for a peaceful stay, offering privacy and comfort close to parks, golf clubs, and shops. Just a short drive from Promenade Bolingbrook and Greene Valley Forest Preserve. Convenient access to highways I-355 and I-55 makes exploring the area easy. Enjoy nearby dining options and beautiful walking trails, making it ideal for travelers seeking relaxation and local adventures.

Guest favourite

The living area features a large sectional sofa with decorative pillows, positioned opposite a television mounted on a dark wood unit. Artwork depicting colorful pixel characters adorns the wall. An archway leads to a game room with a pool table and ambient lighting.

Home in Downers Grove

4.91 out of 5 average rating, 131 reviews

Games, Grounds, Goodness in DG

Our family loves games and when travelling it is great to have entertainment for the whole family. Our game room includes a video arcade game with over 400 options, boardgames and more! Maybe simple cards or puzzles are your preference--we have them all in this fully furnished home with large backyard to play in. Bedroom 1--bunk bed with full on bottom, twin on top Bedroom 2--queen bed with room for a play pen Stay for a weekend or longer and know fun will be had!

Guest favourite

A wooden dock extends into the calm water, framed by lush greenery and trees. Two metal chairs sit on the dock, offering a serene spot to enjoy the lake views.

Home in Downers Grove

4.93 out of 5 average rating, 61 reviews

Lakefront View Getaway Home! Hot tub! Kayak!

INCREDIBLE 5,519 sq. LAKEFRONT HOME with GORGEOUS VIEWS. 30 Minutes Away From Downtown Chicago. 7 Bedrooms, 9 Beds, 2 Additional Sofa Beds & 4 Baths. Fits 20 guests by request. PRIVATE DOCK and PATIO/BACKYARD Right on BROOKERIDGE LAKE. UNICORN ISLAND FLOATING RAFT, KAYAK, PADDLE BOAT, FISHING & MORE. BrookeRidge Private Jet Airport in the Same Park. Indoor Entertainment Including POOL TABLE, AIR HOCKEY, PING PONG, DARTS, CARD GAMES, GAMING CONSOLE & KARAOKE 🎤