Vacation rentals in Darien

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

Home in Glen Ellyn

Beautiful 5 bedroom, 2.5 bath home in Glen Ellyn, fully furnished with everything you may need for a wonderful stay! Located in the peaceful suburbs of Glen Ellyn, the area is perfect for families or friends who would like a comfortable getaway. Located 40 minutes from downtown Chicago and Midway airport and 30 minutes from O'Hare airport. Located nearby major highways and shopping centers. Large, private and completely enclosed backyard perfect for kids to play in or a relaxed evening of BBQ!

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.

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.

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!

Elegant Escape in Top Location

This fully equipped home is just minutes from Burr Ridge Village Center with easy access to restaurants, bars, shopping, and local breweries. Outdoor enthusiasts will love the proximity to parks, golf courses, and scenic trails, perfect for hiking, biking, or a leisurely stroll. For those wanting to explore further, downtown Chicago is easily reachable via nearby bus or train options, offering the best of both worlds—peaceful suburban retreat with vibrant city life just a short trip away.

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.

Springside Retreat: Charming Chicago Suburb

Enjoy a clean, comfortable stay in a quiet suburban home designed for real living—not just sleeping. Ideal for families, professionals, and longer stays, this well-maintained home offers space, privacy, and a calm residential setting away from city noise. Inside, you’ll find generous living areas, a practical layout, and thoughtful furnishings that make it easy to settle in. Whether you’re working remotely, visiting family, or staying longer term, the home is set up to be comfortable.

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.

“Aunt Betty’s Cottage” sleeps up to 6 Large yard

Perfect cottage living sleeps up 6 adults c Westmont. Decor is vintage chic with a focus on retro arts and collectibles. Cozy blankets and whimsical art adorn the walls. Perfect for folks who love cute quaint CLEAN and comfy not Kondo! A place to call home where the barn door closes off the Living room. A dinner for 6 in the quaint dining area. Laundry room in the home. New fenced yard out door furniture. Beyond pet friendly we have many accessories for Dogs.

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!

Sleeps 10 • Everyone Stays Together Pets too

📍20 Mi to McCormick • 18 Mi to Rosemont 💼 10 min to Oak Brook Hills & conference venues. 🏆 Sleeps 10 — perfect for teams & groups. 🛋️ 4BR home with workspace & fast WiFi . 🧺 In-unit washer/dryer for gear & wardrobe. 🍳 Full kitchen, dining for 6. 🎱 Fuseball table + board games for downtime . 🚗 Free parking for vans & carpools . 🐾 Pet-friendly. 🚆 5 min drive to Metra, direct to Chicago. 🏕️ Your team's basecamp near it all!