House holiday rentals in Bolingbrook

4.8 out of 5 average rating, 122 reviews

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

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

ValueFamilyParks

4.92 out of 5 average rating, 128 reviews

Home in Carol Stream

Lake Home Retreat-HotTub• FirePit• Kayak• Fishing!

Come enjoy our beautiful home it's the perfect place to relax, unwind & enjoy peaceful lake views. Whether you’re fishing, soaking in the hot tub or sipping coffee on the deck, it’s a quiet home away from home on a serene cul-de-sac. Enjoy stunning views of the lake while grilling or relaxing by the firepit on the beautifully landscaped patio & in the hot tub 🥂 🐶 Up to 2 furry babies are welcome & they’ll love the almost 1-acre fenced yard! 🌅 See weekly & monthly discounts for longer stays

ValueFamilyPets

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.

4.92 out of 5 average rating, 164 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

FamilyLocationCondition

4.89 out of 5 average rating, 217 reviews

A cozy living room features a brick fireplace as a focal point, surrounded by comfortable leather seating arranged for relaxation. Light-colored curtains frame large windows, while a plush area rug adds warmth to the wooden floor. A wooden door and wall decor complement the inviting space.

Home in Glen Ellyn

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!

LocationValueDecor

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.

4.86 out of 5 average rating, 181 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!

FamilyValueCondition

4.87 out of 5 average rating, 155 reviews

The living area features a large sectional sofa with decorative pillows, positioned opposite a television mounted on a dark wood unit. Artwork depicting colorful pixel characters adorns the wall. An archway leads to a game room with a pool table and ambient lighting.

Home in Downers Grove

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!

FamilyLocationAccess

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.

4.86 out of 5 average rating, 170 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.)!

LocationFamilyWalkability

4.99 out of 5 average rating, 105 reviews

A single-story brick home with a well-maintained front yard features green shrubs and a neat pathway leading to the entrance. Large windows allow natural light to illuminate the interior, while a tree provides shade near the entrance.

Home in Brookfield

Cozy Home in Brookfield

Discover tranquility just minutes from the busy city life! Nestled in the heart of Brookfield, IL, our charming home offers the perfect blend of suburban serenity and urban convenience. Just an 8-minute walk from the train station, you'll find easy access to downtown Chicago while enjoying the peaceful atmosphere of our neighborhood. Max 4 overnight guests. No parties or events. Pets allowed (no exotic pets or animals with a bite history).

ValueLocationNearby

4.99 out of 5 average rating, 153 reviews

A welcoming living room is highlighted by a comfortable sectional sofa with decorative pillows. A patterned area rug covers the hardwood floor, and a reading nook features a unique egg chair. Artwork adorns the walls, complemented by greenery from potted plants.

Home in Lombard

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!

FamilyValueAccuracy

4.9 out of 5 average rating, 137 reviews

A cozy living area is shown, featuring a blue leather couch with decorative pillows. An artistic fish sculpture adorns the wall beside colorful, patterned wallpaper. A small dining table with stools is visible, along with a refrigerator and natural light streaming through the window.

Home in Lockport

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 SW of Chicago. Minutes away from I-80, I-55, and I-355.🌿

LocationFamilyKitchen

4.96 out of 5 average rating, 189 reviews

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

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.

ValueLocationNearby

4.96 out of 5 average rating, 136 reviews

A comfortable living area is highlighted by a leather couch adorned with a yellow cushion. A wooden coffee table sits at the center, topped with a vase of bright flowers. A large television is mounted on the wall, while a desk and chair are positioned near the window.

Home in Wheaton

Beautiful Redone Townhome Next to Wheaton College

This townhome is steps across from the Wheaton College Soccer and Football fields. Fully updated with new floors, paint, bathrooms, and furniture. Lots of space to spread out and many working areas. Close to both downtown Wheaton and Downtown Glen Ellyn where wonderful restaurants abound. 2 parking passes included for parking vehicles.

FamilyValueComfort

Popular amenities for Bolingbrook house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.8 out of 5 average rating, 60 reviews

A sparkling pool is framed by a spacious patio, featuring lounge chairs and tables for relaxation. Nearby, a playground is visible, along with a covered seating area and a Blackstone grill, all surrounded by greenery and a serene setting.

Home in Plainfield

Pool, 30 mins to CHI, 3 Kings, Outdoor Space, BBQ

ValueLocationSleep quality

5.0 out of 5 average rating, 42 reviews

A well-maintained in-ground pool is shown surrounded by a concrete deck and lush greenery. A wooden fence encloses the yard, offering privacy. Tall trees and shrubs provide a natural backdrop, while the bright blue sky adds to the inviting atmosphere.

Home in Crystal Lake

Hot tub. Heated Pool. In town location.

ValueFamilyAccuracy

4.96 out of 5 average rating, 49 reviews

Home in St. Charles

The Fox River Farmhouse-walk to downtown and pool

FamilyLocationBathroom

4.92 out of 5 average rating, 98 reviews

Home in Schererville

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking

FamilyValueSleep quality

4.97 out of 5 average rating, 60 reviews

Home in Schaumburg

Backyard Paradise/ Private Pool + Peaceful Stay

FamilyValueOutdoor spaces

4.93 out of 5 average rating, 27 reviews

A spacious living area features a light-coloured sofa set positioned around a wooden coffee table, with a television mounted on the wall. A large area rug enhances the space, while plants and natural light provide a fresh atmosphere. Dining space is visible in the background.

Home in Schaumburg

Paradise with Pool & Games

FamilyLocationDecor

4.89 out of 5 average rating, 18 reviews

The exterior of a spacious two-story home is shown, featuring a mixture of brick and siding. Lush green landscaping surrounds the house, with trees casting shade across the front yard. A paved driveway leads to a garage, and a clear blue sky provides a bright backdrop.

Home in Carol Stream

Spacious 4 Bed/3.5 Bath Sleeps 8+

LocationFamilyGetting around

4.97 out of 5 average rating, 29 reviews

Home in Montgomery

5 bdrm 7 bed 2.5 bth Ranch w Fenced Yard Sleeps 10

LocationFamilyQuiet

Weekly house rentals

4.87 out of 5 average rating, 103 reviews

A spacious living room features a rich blue accent wall and mid-century modern furniture. Two armchairs and a plush sofa are arranged around a low coffee table. A television is mounted on the wall, complemented by decorative wall art. Natural light fills the room.

Home in Westchester

Modern 2Bdrm Westchester/Chicago Home.With Hot tub

FamilyLocationCleanliness

The kitchen features modern white cabinetry with sleek countertops and stainless steel appliances. A central island with a wooden top provides additional workspace. Two woven barstools are situated at the island, and natural light enters through the dual windows, illuminating the space.

4.85 out of 5 average rating, 153 reviews

Home away from home

LocationFamilyComfort

4.97 out of 5 average rating, 106 reviews

The kitchen features modern white cabinetry and stainless steel appliances, complemented by a spacious island with a decorative tray. Natural light floods the area through the nearby window, and a stylish backsplash adds an elegant touch to the space.

Home in Batavia

Bliss in Batavia near the Fox River

LocationFamilyDecor

4.97 out of 5 average rating, 103 reviews

A spacious living area features a large sectional sofa adorned with throw pillows and a soft blanket. A flat-screen TV is mounted on the wall opposite, and natural light streams in through multiple windows, creating a bright, comfortable space.

Home in Geneva

Spacious 4BR Modern Home—Walk to Downtown Geneva!

LocationValueLaundry

5.0 out of 5 average rating, 9 reviews

Spacious 4BR Tudor with Patio near Downtown

FamilyLocationAccuracy

5.0 out of 5 average rating, 25 reviews

A Spacious, Well Stocked, Family-Friendly Retreat

ValueFamilyLong stay

The exterior of the house is framed by lush greenery and mature trees, creating a natural boundary. A well-maintained driveway leads to a two-car garage, while the inviting entrance is accentuated by a landscaped garden with stone edging.

4.74 out of 5 average rating, 80 reviews

Peaceful Bolingbrook Getaway

ValueFamilyIndoor spaces

A hot tub is featured in a wooden deck area, surrounded by lush greenery. Two wine glasses and a bottle of red wine are placed on the edge, adding to the relaxing ambiance. The background includes a wooden fence, providing privacy.

4.95 out of 5 average rating, 38 reviews

Naperville-Bolingbrook, Hot Tub, 10 beds, Jacuzzi

FamilyLocationComfort

Private house rentals

4.92 out of 5 average rating, 13 reviews

Grateful: 3BR - 1BT Modern Getaway

LocationFamilyIndoor spaces

5.0 out of 5 average rating, 13 reviews

Home in Plainfield

Spacious 4BR, 2 Living Rooms Family & Pet Friendly

LocationFamilyCleanliness

4.91 out of 5 average rating, 44 reviews

A modern kitchen showcases stainless steel appliances, including a refrigerator and range. Wood cabinetry offers ample storage, complemented by elegant tile backsplash. Natural light enters through a window, illuminating the wood-look flooring and creating a warm atmosphere for meal preparation.

Home in Warrenville

“The Relaxing Oasis Near Expressway”

ValueLocationSleep quality

4.86 out of 5 average rating, 80 reviews

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

Captivating Home near Naperville

FamilyLocationCheck-in

4.93 out of 5 average rating, 80 reviews

A comfortable living area features a light gray sofa positioned next to a white entertainment unit. A flat-screen TV is mounted on the wall, and a large area rug with intricate patterns covers the hardwood floor. Natural light from the windows brightens the space.

Home in Lisle

Cute & Cozy Lisle, IL House Near the Best Areas

ValueFamilyWalkability

4.92 out of 5 average rating, 59 reviews

A comfortable living area features a green sofa alongside brown armchairs, creating a cozy seating arrangement. Natural light filters through large windows adorned with wooden shades. A coffee table sits in the center, complemented by decorative plants, while artwork adorns the walls.

Home in Lockport

Around the Block

LocationValueBreakfast

5.0 out of 5 average rating, 52 reviews

A spacious living area features hardwood floors and high ceilings, providing a welcoming ambiance. Modern furniture includes a light-colored sofa and a round coffee table. An entertainment system is positioned near a large window, while a dining table is visible in the adjacent space.

Home in Aurora

Spacious 4 Beds w/ Yard – Near Naperville, Chicago

FamilyLocationLong stay