Family-friendly vacation rentals in Woodridge

4.92 out of 5 average rating, 164 reviews

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

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

FamilyKitchenBackyard

4.91 out of 5 average rating, 182 reviews

A bright living area features a comfortable sofa arranged around a modern coffee table. A work desk is positioned near the window, with natural light spilling in. Artwork adorns the walls, and greenery adds a touch of life to the space, enhancing the welcoming atmosphere.

Apartment in West Dundee

Charming Riverfront Stay | Heart of Downtown

Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

Indoor spacesKitchenTV

4.94 out of 5 average rating, 890 reviews

A treehouse elevated above ground showcases a wooden exterior with a balcony. An inviting staircase leads to the entrance, surrounded by lush greenery and vibrant leaves creating a natural setting. The sturdy structure is supported by wooden beams, blending harmoniously with the surrounding trees.

Treehouse in Schaumburg

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot/cool tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

FamilyKitchenHeating

4.88 out of 5 average rating, 112 reviews

A comfortable living area features a patterned sofa and armchair, positioned near a decorative fireplace. A small table is set with items, while a dining area is visible in the background. Natural light enters through the window, enhancing the cozy ambiance.

Apartment in Lemont

Burr Oak

Nestled in the Palos Forest Preserve with access to many miles of hiking and biking trails . Spacious one bedroom basement apartment with private entrance. 6 minutes to The Forge, 7 minutes to Target, 8 minutes to downtown Lemont restaurants. 4 minutes to Little Red Schoolhouse, 7 minutes to Burr Ridge shopping and dining. 22 minutes to Midway 32 minutes to O'Hare. Half hour to the Loop. 20 minutes from Ikea and Bass Pro. Very quiet cabin like setting. Ask about our extended stay discounts.

KitchenIndoor spacesBackyard

4.86 out of 5 average rating, 182 reviews

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

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!

Indoor spacesKitchenAccess

4.84 out of 5 average rating, 146 reviews

Home in Westmont

“Aunt Betty’s Cottage” sleeps up to 6 Large yard

Perfect cottage living sleeps up 6 adults c Westmont. Decor is vintage chic with a focus on retro arts and collectibles. Cozy blankets and whimsical art adorn the walls. Perfect for folks who love cute quaint CLEAN and comfy not Kondo! A place to call home where the barn door closes off the Living room. A dinner for 6 in the quaint dining area. Laundry room in the home. New fenced yard out door furniture. Beyond pet friendly we have many accessories for Dogs.

KitchenFamilyLocation

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!

KitchenIndoor spacesBackyard

4.87 out of 5 average rating, 181 reviews

A living area features a brown leather sofa accompanied by two accent chairs, all arranged around a glass-top coffee table. Natural light enters through a large window adorned with flowing curtains, complemented by a decorative mirror and wall-mounted storage.

Home in Lisle

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!

KitchenIndoor spacesValue

4.93 out of 5 average rating, 164 reviews

The exterior of the vintage garage apartment is shown, featuring a bright yellow facade with two white garage doors. A large window is positioned above the doors, with greenery surrounding the property, contributing to the charming appearance.

Guesthouse in Villa Park

Eclectic Coach House Apartment

Vintage Charmer! 1935 Sears Craftsman Coach House garage apartment. Beautiful safe neighborhood surrounded by historic homes and just steps from the Illinois prairie path, parks, brewery's/bars, restaurants and more! With an eclectic boho chic vibe, featuring full kitchen and on site private washer/dryer. Overlooking an accessible lovely backyard! Close to airports and easy access to public transportation/major highways. Just 30 min from the Chicago Loop!

FamilyKitchenBiking

4.85 out of 5 average rating, 155 reviews

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.

Home in Naperville

Home away from home

Perfect location, walk/bike to downtown area/ High Speed Wifi throughout the house / 2 King size beds one Queen bed /Newly remodeled / Huge back yard / Brand new appliances / Space for your car in a garage or plenty of parking on long driveway/ Outside porch with seating / Pet friendly - no deposit or any other charge. This is my first house ever listed I will add to the describtion more, after people will notice more things, too many to list.

Indoor spacesFamilyLong stay

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).

KitchenFamilyHeating

4.94 out of 5 average rating, 135 reviews

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.

Apartment in Warrenville

“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!

FamilyIndoor spacesCheck-in

Popular amenities for Woodridge family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guesthouse in Merrillville

4.92 out of 5 average rating, 196 reviews

We have Power Couples getaway

Indoor spacesFamilyPool

4.87 out of 5 average rating, 133 reviews

A spacious outdoor deck is covered with a bright shade sail, providing relief from the sun. Comfortable wicker chairs with soft cushions create a cozy seating area, overlooking the peaceful river and surrounding greenery.

Home in Algonquin

The River House Sauna/Kayaks/Hot Tub/Fire Pit

FamilyKitchenCleanliness

4.88 out of 5 average rating, 392 reviews

The exterior of a charming coach house is presented, featuring wooden shingles and a well-maintained yard. A circular table with chairs is set on the lawn, accompanied by a green umbrella for shade. Lush bushes border the property, and a wooden fence encloses the yard.

Guesthouse in Chicago

Private Coach house near Lincoln Square!

Indoor spacesFamilyTV

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

FamilyIndoor spacesDecor

Guest suite in Riverwoods

A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.

4.95 out of 5 average rating, 503 reviews

Master qtr close to nature & easy urban facilities

Indoor spacesFamilyView

4.97 out of 5 average rating, 180 reviews

Condo in West Town

Chicago Oasis | Spa Bath, Patio & Fireplace

FamilyIndoor spacesComfort

4.96 out of 5 average rating, 104 reviews

A large, inviting above-ground pool features clear blue water, with a pink flamingo float resting on the surface. Surrounding trees provide natural shade, while a gazebo with soft lighting is visible in the background, offering a cozy and relaxing ambiance.

Guest suite in Flossmoor

Fun game-room suite with hot tub & optional Yurt

KitchenFamilyGrill

4.9 out of 5 average rating, 135 reviews

Home in Montgomery

Skip the hotel! Relax here!

Indoor spacesFamilyCondition

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 138 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

FamilyIndoor spacesCheckout

Guest suite in Plainfield

A spacious living area is visible, featuring a large, comfortable sectional sofa facing a mounted television. A coffee table sits in front, surrounded by a decorative area rug. The adjoining kitchen and dining space are seen in the background, showcasing wooden cabinetry and a dining table for four.

4.9 out of 5 average rating, 107 reviews

Relaxing Suite with Independent Entrance

KitchenFamilyGetting around

4.89 out of 5 average rating, 218 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

Indoor spacesKitchenOutdoor spaces

4.88 out of 5 average rating, 252 reviews

A cozy living room features a leather sofa with decorative pillows, accompanied by two woven chairs. A coffee table sits on a patterned rug, while a potted plant and framed artwork add visual interest. Natural light enters through large windows, creating a bright atmosphere.

Home in Plainfield

Modern Peaceful Home | Firepit | Steps to Downtown

FamilyIndoor spacesPets

Apartment in Downers Grove

A cozy sleeping area is featured, showcasing a spacious bed dressed in a light-colored quilt. A window above allows natural light to filter in, enhancing the serene atmosphere. Potted plants and artwork adorn the space, providing a touch of warmth.

4.76 out of 5 average rating, 127 reviews

Private Studio Unit

Indoor spacesKitchenDecor

4.88 out of 5 average rating, 185 reviews

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

1920s fully updated unique open artist loft space

FamilyIndoor spacesNearby

4.95 out of 5 average rating, 119 reviews

A spacious living area features a large L-shaped sofa adorned with decorative cushions. A coffee table sits at the center, complemented by a cozy area rug. A brick fireplace, currently not in use, adds character, while a wall-mounted Smart TV is positioned above the mantel.

Home in Schaumburg

Pet-Friendly Sunny 3BR Near Woodfield & Downtown

Indoor spacesKitchenBathroom

4.91 out of 5 average rating, 562 reviews

A modern kitchen showcases dark wood cabinetry and stainless steel appliances, including a refrigerator and gas stove. A granite countertop extends into a bar area with three metal stools. A microwave and kettle are placed on the counter, illuminated by overhead lighting.

Guest suite in Wood Dale

The Deer Suite

FamilyKitchenView

Family-friendly home rentals with a pool

4.75 out of 5 average rating, 263 reviews

Apartment in The Loop

Stylish Corner 2 Bedroom in the Heart of Chicago |

FamilyIndoor spacesAccess

4.96 out of 5 average rating, 139 reviews

An open-concept living area features large windows that invite natural light and provide a view of the cityscape. A comfortable blue sofa is adorned with patterned pillows, while a light wood coffee table sits in front of it. A dining space with black chairs complements the modern kitchen.

Condo in Evanston

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

KitchenIndoor spacesNearby

Apartment in Downtown Chicago

A rooftop pool area features a long, inviting pool bordered by lounge chairs in various colors. Sunlit trees are visible nearby, and the backdrop consists of modern high-rise buildings, creating a vibrant urban atmosphere.

4.93 out of 5 average rating, 120 reviews

The Metropolitan Retreat (Fitness Center • Sauna)

Indoor spacesKitchenComfort

Condo in Elk Grove Village

The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.

4.92 out of 5 average rating, 123 reviews

Just remodeled apartment close to airport and mall

Indoor spacesKitchenAccuracy

Apartment in Downtown Chicago

4.93 out of 5 average rating, 136 reviews

5-Star Gold Coast Experience in a Luxe 2BR Retreat

KitchenIndoor spacesSleep quality

4.9 out of 5 average rating, 600 reviews

A cozy bedroom features a spacious bed dressed in bold black and white striped bedding. A decorative red pillow adds a pop of color. A framed artwork of a rabbit is displayed above the bed, complemented by bedside tables with a lamp and a small potted plant.

Apartment in Uptown

Whole Flat in Private Club. Walk to L, Dining & Shows

Indoor spacesKitchenAccuracy

Guest suite in Saint Charles

A spacious bedroom features a queen bed dressed in crisp white linens, accompanied by decorative pillows. Soft lighting is provided by a bedside lamp, while an accent rug adds warmth to the wood floor. A built-in shelf displays various decorative items.

5 out of 5 average rating, 323 reviews

Peaceful Private Coach-House in St. Charles

KitchenIndoor spacesLocation