Vacation rentals in Darien

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Top-rated vacation rentals in Darien

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Superhost

Condo in Westmont

4.76 out of 5 average rating, 29 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 favorite

Apartment in Lemont

4.87 out of 5 average rating, 79 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 favorite

Home in Westmont

4.91 out of 5 average rating, 11 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 favorite

Home in Westmont

4.94 out of 5 average rating, 62 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 favorite

Condo in Westmont

4.88 out of 5 average rating, 42 reviews

Cozy condo near Chicago

Built in 1976, this charming apartment offers plenty of space for the whole family to enjoy. With a great connection to major highways and just a short drive to downtown Chicago. • Located on the second floor (please note: no elevator) • Pet-friendly (fee applies) • Shared washer and dryer in the lower-level common area (coins provided) • Over 10 free parking spaces available just behind the building • No smoking inside the unit or building • No parties allowed

Guest favorite

Home in Downers Grove

4.91 out of 5 average rating, 116 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 favorite

Home in Downers Grove

4.93 out of 5 average rating, 45 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

Home in Woodridge

4.86 out of 5 average rating, 43 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 favorite

Tiny home in Burr Ridge

4.9 out of 5 average rating, 396 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

Top guest favorite

Home in Lombard

4.99 out of 5 average rating, 121 reviews

Modern Boho house in Lombard 7 min to Metra

Kick back and relax in this calm, stylish space. Visiting family in Chicagoland area? Traveling for work? Lombard is centrally located 30 min to everywhere! The house is only 6 min to Oakbrook Shopping and Business Center and upscale shopping and fabulous restaurants like RH with rooftop restaurant, 8 min to Yorktown Shopping Center. Whatever your travel purpose is, we will be happy to host you! Welcome home!

Guest favorite

Apartment in Westmont

4.91 out of 5 average rating, 46 reviews

Harmony Haven - 2 Parking Spaces!, Sleeps 4!

Step into your perfect getaway in Westmont! Just steps away from the Westmont Metra station, this stunning apartment is the perfect cozy and welcoming space for up to 4 guests. Enjoy a relaxing stay with all the comforts and amenities you need for an unforgettable getaway. Ready to experience it for yourself? Click the 'Reserve' button and secure your stay today!

Guest favorite

Apartment in Downtown Naperville

4.87 out of 5 average rating, 179 reviews

Comforts of home in downtown Naperville

Cozy 1 bedroom garden level apartment located in downtown Naperville. Short walking distance to great shopping and many fine restaurants. Also short walking distance to train which goes directly to Chicago. Parking is available for 1 car in driveway. Professionally cleaned after every guest visit, as well as free cleaning offered for stays of two weeks or longer.