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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
4.8 out of 5 average rating, 112 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 spacious artist loft features a living area with hardwood floors and large windows allowing natural light. A leather sofa is positioned in the center, with stylish chairs nearby. The open kitchen is visible in the background, along with a modern dining space under soft lighting.
Loft in Brookfield
4.89 out of 5 average rating, 163 reviews

1920s fully updated unique open artist loft space

True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

Guest favourite
Flat in Cathedral Area
4.94 out of 5 average rating, 240 reviews

*The Belltower Haven*Large*Family Friendly*Wi-Fi

Our remodeled spacious apartment is located on Plainfield Road, minutes away from 1-80 & 1-55. Near: Rialto Theatre, Haley Mansion, Jacob Henry Mansion, Train Station, College of St. Francis, Joliet Junior College, Slammers Minor League Baseball and St. Joe's Hospital, New Lenox Sports Complex Minutes away from: Chicagoland Speedway, Hollywood Casino, Lewis University and Silver Cross Hospital. 30 minutes from Chicago 3 br (3 Queens beds 1 queen sleeper sofa, queen air mattress), 1 full bath

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
4.86 out of 5 average rating, 170 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 single-story ranch home is presented with a dark blue exterior and white shutters. A neatly trimmed lawn and concrete pathway lead to the front door. Flanking the entrance, small shrubs add greenery, while a tall evergreen tree stands nearby.
Home in Montgomery
4.88 out of 5 average rating, 164 reviews

Nice, Private Ranch Home

Nice private ranch home in a quiet neighborhood. Fox River and the river bike trail are only 3 minutes away, Rush Copley Medical Center, lots of shopping and dining options within minutes, Phillips park zoo, and water park very close, major roadways to Chicago. 10 min, from downtown Aurora where you can find the Hollywood Casino, Paramount theatre, many shopping stores and you can enjoy a walk along the Fox river, Fox valley mall and the Chicago premium outlets mall are only 20min away.

Guest favourite
A cozy bedroom features a comfortable bed with a quilted cover and decorative pillows. A colorful textile art piece depicting Route 66 is displayed on the wall. A side table with a lamp adds to the charm, complemented by a vintage photograph hanging above.
Home in Lockport
4.96 out of 5 average rating, 171 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"! *Note: Pricing is based on "Double Occupancy". Extra charges per person apply after 2 guests. Can accommodate up to 6 guests. 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"!

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, 245 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 modern two-story home with a welcoming facade features large windows and an inviting entrance. The lawn is well-maintained, surrounded by colorful flower beds, and a driveway leads to a two-car garage. A flag hangs prominently, enhancing the home's character.
Home in Bolingbrook
4.83 out of 5 average rating, 82 reviews

Modern, Spacious, & Convenient 4 BR/3.5 BA Home

Modern single family home with over 3500 sq ft including finished basement. Our 4 bedroom, 3.5 bathroom home includes 1 king bed, 2 queen beds, 1 Full bed, 1 Twin Bed and 1 sofa sleeper. The finished basement is fully equipped for entertaining. Free cable, high speed internet and 3 Smart TVs are included. Enjoy beautiful open views from the backyard deck. Minutes away from shopping, dining, and entertainment at The Promenade. Easy access to major highways and airports.

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, 162 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
4.96 out of 5 average rating, 103 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!

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
4.91 out of 5 average rating, 150 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
The exterior of the Victorian Sherwood House showcases its distinct pink siding accented with green trim. Stained glass windows add character, and multiple gabled roofs enhance its architectural design. A canopy of trees provides a natural backdrop to this charming residence.
Flat in Elgin
4.8 out of 5 average rating, 196 reviews

Sherwood House

Enjoy the ambience of the Sherwood House, an 1884 Victorian built for Judge David Sherwood. Use of entire first floor apartment including a full kitchen is perfect for longer term stays. Original features include multiple stained glass windows, beautiful wood work, multiple decorative fireplaces and hardwood floors. Located just blocks from downtown Elgin, walk to shops, restaurants, the casino, bike trail or Metra. WiFi and off street parking.

Popular amenities for Bolingbrook holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Bolingbrook

Home in Crest Hill
4.71 out of 5 average rating, 14 reviews

Family-Friendly 3-Bedroom Townhome |Your Home Away

Guest favourite
A light and airy living room features a decorative fireplace with a minimalist stone surround and a large television displaying a beach scene. A comfortable gray sectional sofa is set against the wall, complemented by a dark geometric rug. A small dining table is positioned nearby, enhancing the inviting layout.
Home in La Grange Park
4.96 out of 5 average rating, 46 reviews

Zen in La Grange Park

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
4.92 out of 5 average rating, 93 reviews

Professionally Sanitized - Dome Away From Home

Superhost
A well-lit indoor pool area features a rectangular swimming pool with steps on one end. Brightly colored walls complement sleek lounge chairs and vibrant red chairs. A drinking fountain is located nearby, while ceiling lights emit a tranquil, soft glow throughout the space.
Hotel room in Naperville
4.79 out of 5 average rating, 180 reviews

Close to Riverwalk | Indoor Pool + Free Breakfast

Top guest favourite
A well-appointed bedroom features a spacious bed adorned with a striped blanket and decorative pillows. Two lamps are placed on matching nightstands beside the bed. Natural light filters through a large window with light curtains, offering a view of the surrounding landscape.
Private room in Naperville
5 out of 5 average rating, 99 reviews

Private room in a nice home w/pond view

Home in Naperville
5 out of 5 average rating, 3 reviews

Naperville Escape, King Bed, Parking, Crib, Patio

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, 24 reviews

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

Guest favourite
A private entrance is seen, featuring a white door framed by a stone wall and surrounded by green foliage. The patio is paved with brick, and a planter with leafy plants adds a touch of greenery near the door.
Flat in Downtown Naperville
4.87 out of 5 average rating, 188 reviews

Comforts of home in downtown Naperville

When is the best time to visit Bolingbrook?

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Avg. price€ 126€ 115€ 128€ 153€ 154€ 133€ 126€ 129€ 126€ 128€ 115€ 127
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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 € 17 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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