Holiday houses 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.
Condo in Westmont
4.82 out of 5 average rating, 39 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

Guest favourite
A single-story ranch-style home is depicted, featuring a brick and siding facade. A two-car garage is positioned on the right side, with a well-maintained lawn and neat landscaping in the front yard. Clear skies and scattered clouds provide an inviting backdrop.
Home in Bolingbrook
4.92 out of 5 average rating, 155 reviews

Spacious Bolingbrook Retreat w/ Garage & Yard

Relax with the whole family at this peaceful and spacious 3-bedroom ranch home conveniently located near I-55 & I-355. Walking distance to Promenade Mall, restaurants, bars, shopping, Bass Pro Shop. Enjoy self check-in with smart lock, private attached 2-car garage, large backyard, patio, and grill. Perfect for families, work trips, or weekend getaways. Clean, safe, and only 30 minutes from downtown Chicago and major attractions. Self check-in Free parking Fast Wi-Fi Washer/dryer Backyard/patio

Guest favourite
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.
Apartment in Lemont
4.87 out of 5 average rating, 105 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.

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, 44 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
4.86 out of 5 average rating, 173 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, 126 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.

Top 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, 264 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 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
4.83 out of 5 average rating, 81 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.

Superhost
The exterior of the house is framed by lush greenery and mature trees, creating a natural boundary. A well-maintained driveway leads to a two-car garage, while the inviting entrance is accentuated by a landscaped garden with stone edging.
Home in Bolingbrook
4.74 out of 5 average rating, 73 reviews

Peaceful Bolingbrook Getaway

Welcome to our charming Airbnb rental located just minutes away from the Promenade Mall in Bolingbrook, Illinois! Located just minutes away from the Promenade Mall, this house is in a prime location for shopping, dining, and entertainment. And, with great access to major highways, it's easy to explore all that the Chicagoland area has to offer. Whether you're in town for a weekend getaway or an extended stay, our charming Airbnb rental is the perfect home away from home.

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
4.88 out of 5 average rating, 147 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!

Top Guest favourite
The living area features a comfortable seating arrangement with a sofa and two armchairs. A round coffee table sits in the center on a patterned area rug. Soft lighting enhances the neutral wall tones, while a decorative plant adds a touch of greenery.
Apartment in Warrenville
4.93 out of 5 average rating, 120 reviews

“The remote retreat”

We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!

Top Guest favourite
A spacious living area features comfortable seating options, including a recliner and an upholstered chair. Natural light filters through large windows, highlighting the wood cabinetry and kitchen area. A small dining table is positioned near the window, enhancing the inviting atmosphere.
Apartment in Naperville
4.99 out of 5 average rating, 102 reviews

Beautiful, quiet, private, spacious, guest suite.

We offer a private entrance with ramp, private deck, shared screened-in porch, gas fireplace, cable with two T.V.’s, kitchenette, washer/dryer, and beautiful views. Our suite is also a wonderful work from home location. We offer fast reliable WiFi, with office supply and copy centers within five minutes of our suite. The suite is on a single level, with all doors being 36 inches wide for accessibility.

Popular amenities for Darien holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. DuPage County
  5. Darien