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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Superhost

A round table with a floral tablecloth is situated in a corner, surrounded by four white chairs. A ceiling fan is installed above, and a framed quote is displayed on the wall nearby. Light filters through sheer curtains, adding a subtle ambiance.

Apartment in Westmont

4.78 out of 5 average rating, 32 reviews

home away from homecondo comfort

Built in 1976, our apartment offers a comfortable and spacious retreat with easy access to major highways and just a short drive to downtown Chicago. • Located on the second floor (please note: no elevator) • Shared washer and dryer available in the lower-level common area (coins provided) • Plenty of free parking just behind the building (more than 10 spaces) Enjoy comfort, convenience, and a peaceful atmosphere in a well-connected neighborhood—perfect for both short visits and longer stays

Superhost

A comfortable living area features a patterned sofa and armchair, positioned near a decorative fireplace. A small table is set with items, while a dining area is visible in the background. Natural light enters through the window, enhancing the cozy ambiance.

Flat in Lemont

4.86 out of 5 average rating, 84 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.

Superhost

Flat in Lisle

4.88 out of 5 average rating, 26 reviews

Taste of Chicago | Cozy & Central Location!

Welcome to our Chicago-themed studio! From deep dish pizza to the Bean, enjoy all that the city offers in this apartment, perfect for a couples getaway or an extended business trip. Comfort and convenience await you, featuring free parking, plush memory foam bed, fully stocked kitchen, free laundry facilities, Kuerig coffee maker and much more! Situated steps from the train station, enjoy a short ride into downtown or explore nearby Naperville, Oakbrook or the beautiful Morton Arboretum!

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, 23 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.

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, 102 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 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

4.99 out of 5 average rating, 200 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

An open living space features a cozy seating area with a gray sofa, complemented by two gray ottomans. Natural light filters through large windows, illuminating the adjacent kitchen with stainless steel appliances. Textured rugs and subtle decor elements create a harmonious and inviting environment.

Home in Westmont

4.94 out of 5 average rating, 69 reviews

Charming Home in Westmont, Close to Chicago!

Very peaceful neighborhood! This house has the best location in the Western Suburbs of Chicago. Walking distance to downtown Westmont and train station. A few minutes drive to malls, parks and everything...eight minutes drive to downtown Downers Grove. 30 minutes drive to downtown Chicago. This house has an appealing open floor plan and a well equipped kitchen. Each bedroom has its own TV. Lower level game room has the most popular board games, toys and an air hockey table.

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, 120 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

4.92 out of 5 average rating, 51 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 🎤

Superhost

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

4.87 out of 5 average rating, 52 reviews

Cozy 1-Bedroom Apartment on the Ground Floor

Cozy 1-Bedroom Apartment on the Ground Floor in a quiet Woodridge neighborhood. 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

A cozy living area features a plush gray sofa accompanied by light-colored ottomans. A glass coffee table sits on a multicolored rug, adding warmth to the space. Natural light filters through sheer curtains, enhancing the modern design complemented by a mounted flat-screen television.

Flat in Berwyn

5 out of 5 average rating, 25 reviews

NEW Jade Haven in Berwyn/Riverside

Step into Jade Haven, where tranquility meets modern elegance. Welcome to Jade Haven your serene retreat of calm and comfort.Inspired by the soothing essence of jade, this one-bedroom suite blends modern elegance with spa-like tranquility. Enjoy a fully equipped kitchen, cozy living area, a serene bedroom designed for restful nights and peaceful mornings. The space features a sleek, airy design with thoughtful touches to make you feel right at home.

Guest favourite

A walkway lined with pavers is framed by greenery, leading toward a fenced yard. Soft string lights illuminate the area beside the tiny house, creating a serene evening atmosphere. A cozy seating area is visible, inviting relaxation outdoors near the lush foliage.

Tiny home in Burr Ridge

4.9 out of 5 average rating, 406 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