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

Condo in Westmont

4.77 out of 5 average rating, 30 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

Townhouse in Westmont

New place to stay

Back Unit | Patio, Balcony, Yard, Smart TVs, W/D

Ideal for work trips or remote stays, this private rear townhouse features fast Wi-Fi, two smart TVs, in-unit washer/dryer, and a dining area perfect for working. Start your day with coffee on the balcony or wind down on the shaded patio overlooking a partially fenced yard. Free on-site parking adds convenience, and the quiet setting ensures restful nights. Located minutes from main roads, dining, shops, & essentials—this home blends comfort, privacy, and productivity in one convenient package.

Guest favourite

Apartment in Lemont

4.88 out of 5 average rating, 80 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

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 favourite

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 favourite

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

4.87 out of 5 average rating, 45 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.

Superhost

Home in Bolingbrook

4.92 out of 5 average rating, 140 reviews

The Sunshine Spot

Relax with the whole family at this peaceful place to stay. Centrally located off I-355 and I-55 major highways . Within walking distance from Promenade Mall ( over 30 plus stores , bars , restaurants ) . Also only about 30 minutes from Chicago. This 3 bedroom ranch has a two car attached garage with private entry ( very safe ) and a huge backyard with Grill . Very spacious and clean ! Thanks and look forward to seeing you at the Sunshine Spot !

Guest favourite

Tiny home in Burr Ridge

4.9 out of 5 average rating, 397 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 favourite

Home in Lombard

4.99 out of 5 average rating, 122 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!

Top Guest favourite

Guest suite in Naperville

4.95 out of 5 average rating, 462 reviews

Cozy Lakeview Studio with Private Access

Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.

Top Guest favourite

Apartment in Hickory Hills

4.97 out of 5 average rating, 61 reviews

Cozy Guest Suite. Private Entry+ Turo Rental

3600 sqf single family home with a Guest Apartment and private entry on the ground level. Your family will be close to everything when you stay at this centrally-located place. Centrally located off of I294, I55, I57 and I80. Easy to and from travel. In Need of a rental we have 2018 Jeep Grand Cherokee High Altitude at the house and listed Turo.