Vacation rentals in Woodridge

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

Family · Value · Parking

Cute & Cozy Lisle, IL House Near the Best Areas

Beautiful 2 bedroom 1 bath house with 2 car garage, private driveway and plenty of parking. With a nice fenced in back yard in one of Lisle'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.

Location · Value · Backyard

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!

Location · Value · Parks

A Spacious, Well Stocked, Family-Friendly Retreat

Your spacious, family-friendly getaway awaits! Centrally located near I-355 & I-55, just 45 minutes from downtown Chicago, 20 minutes from the natural wonders of the Morton Arboretum, 15 minutes from lively downtown Naperville, and 10 minutes from The Promenade. Enjoy lots to do locally, relax in the fully fenced natural backyard with firepit or savor magical evenings on the deck. With comfort, convenience, and plenty of room for all, this is the perfect home away from home for your next stay.

Location · Value · Checkout

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!

Location · Value · Layout

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.

Location · Family · Laundry

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.

Family · Location · Cleanliness

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.

Location · Family · Nearby

Captivating Home near Naperville

A captivating, newly renovated 3 bedroom / 2 bathroom with fully furnished basement. Clean finishes and modern amenities create the perfect, relaxed space for you and your group. Minutes from downtown Naperville! Walk to downtown Lisle for restaurants, shopping, outdoor events, walk to Lisle train station, Lisle Community Park with walking paths, outdoor summer concerts, playing fields, walk to Prairie Walk Pond with weekly French Market May thru Oct, walk to Sea Lion Aquatic Park.

Value · Family · Indoor spaces

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.

Location · Value · Nearby

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!

Family · Location · Hospitality

Cozy House, Main Road Access, Close to Colleges

Our house is perfect for a small group of friends or family looking for a clean, accessible place. It contains 2 bedrooms (a queen & twin bunk beds) & 1 full bathroom, as well as a sleeper sofa with a pullout queen bed. Enjoy our smart TVs, grill or warm up by the fire pit, & even get some work or studying done! Located just minutes from 2 major highways, 2 colleges, Four Lakes Ski Resort, & much much more, the journey is just getting started once you arrive!

Family · Value · Outdoor spaces