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Holiday rentals in Bolingbrook

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Top-rated holiday rentals in Bolingbrook

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The exterior of a two-story house is presented, featuring a light grey siding and blue shutters. A spacious driveway leads to a two-car garage. Lush greenery surrounds the entrance, with a large tree offering shade and a well-maintained lawn completing the inviting front yard.
Home in Plainfield
4.81 out of 5 average rating, 116 reviews

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

Superhost
A single-story ranch-style home is depicted, featuring a brick and siding facade. A two-car garage is positioned on the right side, with a well-maintained lawn and neat landscaping in the front yard. Clear skies and scattered clouds provide an inviting backdrop.
Home in Bolingbrook
4.92 out of 5 average rating, 153 reviews

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

Guest favourite
Home in Bolingbrook
5 out of 5 average rating, 13 reviews

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.

Guest favourite
The exterior of a single-story home is framed by lush green grass and dark mulch landscaping. A welcoming pathway leads to the front door, adorned with a seasonal wreath. A large tree provides shade, and a white fence marks the boundary of the yard.
Home in Naperville
4.87 out of 5 average rating, 172 reviews

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!

Top guest favourite
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Flat in Aurora
4.98 out of 5 average rating, 253 reviews

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.

Superhost
A wooden deck is featured in this image, providing ample space for relaxation and gatherings. The deck is surrounded by lush greenery, with steps leading down to a garden area. Large windows of the house offer a view of the outdoor space.
Home in Bolingbrook
4.75 out of 5 average rating, 72 reviews

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.

Superhost
A modern two-story house features a light, neutral exterior with decorative shutters. The inviting front yard is well-maintained, including colorful shrubs and a manicured lawn. A garage door is visible on the right side, and tall trees frame the property against a clear blue sky.
Home in Naperville
4.86 out of 5 average rating, 165 reviews

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.)!

Guest favourite
Flat in Lockport
4.94 out of 5 average rating, 109 reviews

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!

Top guest favourite
Home in Cathedral Area
4.98 out of 5 average rating, 148 reviews

*The Heron House*/King Bed/Spacious/Remodeled/

Newly remodeled, Spacious Craftsman Style Home in prime location! Quiet neighborhood near major highways: I55 and I80. 30 Mins SW of Chicago, Free Wi-Fi (800+Mbps) and private parking for 4 cars. Walking distance to restaurants and shops! Minutes from: The Rialto Theatre, Univ. of St. Francis, St. Joe's Hospital, Harrah's and Empress Casinos, Haley Mansion, Lewis Univ., Silver Cross Hospital, Chicagoland Speedway, Autobahn CC, and much more!

Top guest favourite
The living area features a comfortable seating arrangement with a sofa and two armchairs. A round coffee table sits in the center on a patterned area rug. Soft lighting enhances the neutral wall tones, while a decorative plant adds a touch of greenery.
Flat in Warrenville
4.93 out of 5 average rating, 113 reviews

“The remote retreat”

We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!

Top guest favourite
A tranquil lake scene is depicted, featuring autumnal trees reflecting vibrant hues of yellow, orange, and red in still water. The grassy shoreline enhances the serene environment, while neighboring greenery contributes to the picturesque landscape.
Guest suite in Naperville
4.96 out of 5 average rating, 533 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
Home in Lockport
4.96 out of 5 average rating, 173 reviews

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.

Popular amenities for Bolingbrook holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Bolingbrook

Top guest favourite
A geodesic dome home is nestled among lush green trees, featuring a sloped roof and large windows that invite natural light. The surrounding yard is manicured with grass and bordered by colorful flower beds, creating a serene outdoor space.
Dome in Naperville
4.93 out of 5 average rating, 94 reviews

Professionally Sanitized - Dome Away From Home

Top guest favourite
The exterior of a single-story brick house is depicted, featuring a spacious driveway and a well-maintained lawn. Large windows allow natural light to illuminate the interior, while a covered entryway provides shelter. The garage door is designed with multiple glass panels.
Home in Orland Hills
4.94 out of 5 average rating, 49 reviews

Beautiful home in Orland hills!

Superhost
A modern dining area features a round wooden table surrounded by four woven chairs. Bright overhead lighting illuminates the space, which connects to a sleek kitchen with stainless steel appliances. Open layout enhances the airy feel, with a cozy seating area visible in the background.
Home in Lisle
4.86 out of 5 average rating, 70 reviews

Captivating Home near Naperville

Superhost
Home in Bolingbrook
5 out of 5 average rating, 4 reviews

Luxe Home with Michelin Star Kitchen & King Beds

The kitchen area is visible, featuring sleek stainless steel appliances and a coffee bar stocked with a variety of Keurig pods. Two bar stools sit at the counter, enhancing the open layout that connects the kitchen to the living area.
Home in Joliet
4.67 out of 5 average rating, 27 reviews

Joliet Retreat: Walk-in Shower + Self Check-in

Home in Naperville
5 out of 5 average rating, 4 reviews

Naperville Escape, King Bed, Parking, Crib, Patio

Guest favourite
A cozy living area is presented, featuring a comfortable sofa with decorative cushions and a matching ottoman. Two lamps provide soft lighting, and a large mirror reflects the space. A textured area rug defines the seating arrangement, with stair access visible in the background.
Flat in Downtown Naperville
4.87 out of 5 average rating, 190 reviews

Comforts of home in downtown Naperville

Superhost
A tranquil bedroom is furnished with a spacious bed adorned with layered bedding and decorative pillows. Two pieces of floral artwork are mounted on the green wall, and natural light filters through a large window, complemented by dark curtains. A wooden dresser and a TV stand are positioned against the walls.
Home in Woodridge
4.77 out of 5 average rating, 26 reviews

Comfy Stay Inn

When is the best time to visit Bolingbrook?

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Frequently Asked Questions

  • What are the best places to stay in Bolingbrook?

    The neighborhoods around The Promenade Bolingbrook, as well as areas near local parks and shopping, are often chosen for convenient access to dining, outdoor spaces, and entertainment. Stays here make it easy to enjoy local activities.

  • What are the best things to do in Bolingbrook with kids?

    Families often explore the Pelican Harbor Indoor/Outdoor Aquatic Park, play at The Promenade Bolingbrook, or enjoy local parks and recreation centers. These spots are known for their engaging activities and kid-friendly environments.

  • What are some of the best things to do in Bolingbrook?

    Explore The Promenade Bolingbrook for shopping and dining, walk trails at Whalon Lake, or unwind at local parks. Community centers and conservation areas provide opportunities to connect with local nature and culture.

  • How is the weather in Bolingbrook?

    Bolingbrook has cold, snowy winters with temperatures often between 19–38°F (-7–3°C), while late spring through summer brings warmer weather around 60–85°F (16–29°C). Rain is most common in spring, so packing layers and a light rain jacket is suggested.

  • When is the best time to visit Bolingbrook?

    Late spring through early fall is often recommended for milder temperatures and outdoor events, with afternoons reaching 60–85°F (16–29°C). Winter visits have cooler weather and a quieter pace, with temperatures regularly below 38°F (3°C).

  • What are the best places to visit in Bolingbrook?

    Many visitors explore The Promenade Bolingbrook for shopping and dining, relax at Whalon Lake, or learn about nature at Hidden Oaks Conservation Area. These spots are often recommended for experiencing the community’s atmosphere.

  • What are some hiking trails in Bolingbrook?

    Bolingbrook has paved and natural walking paths in local parks, often recommended for gentle strolls, nature observation, and birdwatching. Residents frequently explore park trails that are suitable for a variety of experience levels.

  • What are some family activities we can do in Bolingbrook?

    Try swimming and playing at Pelican Harbor Indoor/Outdoor Aquatic Park, mini-golfing, or enjoying hands-on exhibits at local recreation centers. Parks and open spaces host community activities throughout the year.

  • What are some of the best day trip ideas from Bolingbrook?

    Around Bolingbrook, you can explore nature preserves, visit regional museums, or discover vibrant local food scenes in neighboring cities. The broader Chicago area has cultural experiences, gardens, and entertainment for a range of interests.

  • Are there any pet friendly accommodations available in Bolingbrook?

    Many accommodations in Bolingbrook welcome pets and are located near parks and green spaces, making it easier to bring animal companions along. Host policies can vary, so it is helpful to check pet guidelines in advance.

  • What are some local tips for visiting Bolingbrook?

    Locals often suggest bringing comfortable walking shoes for park trails and checking the community calendar for seasonal markets or outdoor events. Early mornings and weekdays can be quieter times at popular parks.

  • What is Bolingbrook known for?

    Bolingbrook is known for its expansive park system, community events, and shopping at The Promenade Bolingbrook. Its blend of recreational facilities and family-oriented activities draws residents and visitors alike.

  • What are the best hidden gems to explore in Bolingbrook?

    Hidden Oaks Conservation Area is often described as a quieter spot for nature walks and wildlife observation. Community gardens and less-visited local parks can also provide a peaceful atmosphere away from busy shopping areas.

  • What are the best foods to try in Bolingbrook?

    Bolingbrook has a mix of locally rooted Midwestern flavors, international cuisines, and classic American fare. Pizzerias, casual grills, and family-owned bakeries are frequently mentioned by locals and travelers alike.

  • What should I bring for a trip to Bolingbrook?

    Pack comfortable walking shoes, layered clothing for changing temperatures, and a light rain jacket, especially in spring. Reusable water bottles and sun protection are useful for exploring parks and outdoor attractions.

  • What is the nightlife in Bolingbrook like?

    Bolingbrook has a laid-back nightlife scene, with local restaurants, sports bars, and casual lounges. Live music and relaxed gathering spots are frequently found around The Promenade Bolingbrook area.

  • What are the most popular events or festivals in Bolingbrook?

    Bolingbrook hosts community festivals in summer, farmers markets, and celebrations around the Fourth of July. Seasonal events in parks and at The Promenade Bolingbrook are frequently suggested for visitors of all ages.

  • Are there family friendly vacation rentals in Bolingbrook?

    Bolingbrook has a variety of family-friendly vacation rentals, often featuring multiple bedrooms, kitchens, and comfortable living areas. Many hosts welcome children and can provide amenities that help make travel with little ones easier.

Quick stats about holiday rentals in Bolingbrook

  • Total holiday rentals

    Explore 50 holiday rentals in Bolingbrook

  • Nightly prices starting at

    Bolingbrook holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 1,400 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Bolingbrook holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Bolingbrook rentals

  • 4.8 Average rating

    Bolingbrook stays are highly rated by guests – averaging 4.8 out of 5!

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