Family-friendly holiday rentals in Bolingbrook

Tranquil 4BR in Naper/Plainfld

Discover our spacious four-bedroom retreat, featuring a master suite with a luxurious bathroom, two queen bedrooms upstairs, downstairs bedroom with two beds, workspace, and a large TV. The living room offers a smart TV and comfy couch, while the kitchen is fully renovated and equipped. Enjoy outdoor amenities like a fire pit, playground, patio set, and grill. Additionally, an easy access to Route 59, I-55, I-88, dining, shopping, and services. Experience comfort and convenience in this charming

Indoor spaces · Family · Walkability

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

Indoor spaces · Kitchen · Layout

Large Luxury Home: King Beds, Theater & BBQ

Relax and enjoy this sunny, fully outfitted family haven! ### FUN: Finished basement with a Movie Theater (projector), ping-pong, and PlayStation. We even have a toy-filled dresser for the kids! ### COMFORT: Fully stocked chef’s kitchen (mixer/Air Fryer), King/Queen beds, and a large master suite. ### PERKS: Huge yard with a stone patio, grill, and fire pit. Includes a 2-car garage and in-home laundry. ### SAFE: Professionally cleaned and sanitized before every stay for your peace of mind.

Indoor spaces · Kitchen · Location

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!

Indoor spaces · Kitchen · Long stay

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!

Family · Indoor spaces · Quiet

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.

Indoor spaces · Kitchen · Checkout

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.

Family · Indoor spaces · Condition

California King Bed | Fast Wi-Fi | 75" Smart TV

Our 3bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful, quiet neighborhood. Built w/ cathedral ceilings, there is plenty of space for 10 people to sleep comfortably (6 beds & several comfy couches), as well as 3 smart TVs, an indoor fireplace, a gas grill & large yard (including outdoor games), a desk space, & more. Enjoy close access to main roads & large stores (Costco, Walmart, hardware stores, etc.)!

Kitchen · Indoor spaces · Barbecue

Lockport Farmhouse: Private Entry+Parking By Door

Welcome to our charming Airbnb retreat in Lockport, Illinois! Enjoy the convenience of a full kitchen equipped with sleek stainless steel appliances. Kick back and relax in the cozy living room with a 55-inch smart TV featuring Roku for your entertainment needs. Convenience meets comfort with access to our on-site laundry room. Experience the perfect blend of modern amenities and rustic charm during your stay in Lockport. Book now for a delightful getaway!

Indoor spaces · Kitchen · Pets

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!

Kitchen · Indoor spaces · Quiet

Island Time - Murals and more

Our charming and crooked, tropical-themed house🌴 is located one block from lively historic downtown Lockport. We are two blocks from train tracks, I & M Canal, and The Public Landing Restaurant. Near to Dellwood Park, Illinois State Museum, Lewis University, Joliet Junior College, Silver Cross Hospital, Chicagoland Speedway, and 30 miles southwest of Chicago. Minutes away from I-80, I-55, and I-355.🌿

Indoor spaces · Family · Check-in

Lockports Famous Hideaway ~ 2bdrm Guest House Flat

A history buff’s dream filled with antiques & artifacts relating to Chicago, Joliet, Lockport, the I & M Canal & "Route 66"! Family & Business Friendly. The entire upstairs 1,500 sq ft vintage 2-bedroom house apartment is all your own space. The flat is NOT shared with other guests/host. Private-entrance/self-check-in. Have a 'historic' stay at the "Hideaway"! Can accommodate up to 6 guests.

Family · Kitchen · Getting around