Family-friendly vacation rentals in Rolling Meadows

4.92 out of 5 average rating, 128 reviews

An outdoor patio is illuminated by string lights, creating a cozy ambiance. The hot tub is set against a backdrop of snowy ground, with comfortable seating arrangements nearby. The lake is visible in the background, enhancing the tranquil atmosphere.

Home in Carol Stream

Lake House Escape •Hot Tub, Bar, Fishing, Firepit

Visiting Chicago this holiday season? Stay somewhere that truly feels like home. We’re opening our personal lake home to guests & would love to welcome u! Tucked awayi n a peaceful neighborhood- the perfect place to gather w/ family, relax & enjoy beautiful lake views. Spend mornings w/ coffee on the deck, afternoons fishing, grilling & evenings soaking in the hot tub or sitting by the firepit. 1-acre fenced yard to enjoy-pets welcome Come settle in, make memories & enjoy our home as your own. ♡

Indoor spacesFamilyComfort

The open living area features a modern dining table set for four, complemented by a spacious kitchen visible in the background. A comfortable seating area is arranged with plush couches and decorative pillows, illuminated by natural light from large windows.

4.97 out of 5 average rating, 195 reviews

Modern Spacious Quiet Home Near O'Hare -Deck&Yard

Experience a modern and quiet retreat in our big 4 Bedroom 2.5 Bathroom home. Perfect blend of comfort and convenience. Sleeps 9 people. Master Suite. Bedrooms: 3 King and Two Full Beds. 6 Smart TVs. Open floor plan with fully equipped kitchen where you can cook and create experiences with family. Big Fenced Back yard with a Big Deck. Parking 3 cars. Close to restaurants, shopping, trails, and parks. 6 miles to Schaumburg Convention Center, 17 miles to O'Hare Airport, 5 miles to Woodfield Mall

FamilyKitchenWalkability

4.94 out of 5 average rating, 897 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*)

Fall's here, the treehouse is warm and cozy, and the hot tub ready for cool nights! 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!

Indoor spacesKitchenWalkability

4.91 out of 5 average rating, 193 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 spacesKitchenDecor

4.97 out of 5 average rating, 134 reviews

The spacious family room features a high vaulted ceiling with exposed wooden beams. A stone fireplace provides a central focal point, and a large TV is mounted above it. Comfortable seating is arranged for relaxation, complemented by a stylish area rug.

Home in Des Plains

NEW~2 Spa Baths~Game Room~Prime Area~Big Yard~

✅Updated Home- RARE 1/3+ Acre Fenced Yard 🏠 ✅Huge Vaulted Ceiling Family Room 🛋️ ✅2 Full Updated Bathrooms on Main Level🪥🛀 ✅Game Room w/Air Hockey & Basketball🏒🏀 ✅Dining Room Seats 10🪑 🍽️ ✅Quiet Neighborhood + Convenient Location🏘️ ✅Open Kitchen Floorplan 🍳👨‍🍳 ✅Outdoor Seating🌳 ✅EZ Driveway Parking for 4 Cars🚗🏎️ ✅Close to O’Hare Airport(8 Min)🛫 ✅Close to Stephens Convention Center(12 Min)👨‍👩‍👧‍👧 ✅Close to Allstate Arena(7 Min)🎤 ✅Close to River’s Casino(8 Min)♥️🎰

KitchenFamilyBathroom

Townhouse in Hoffman Estates

A cozy living area features a black leather sofa paired with decorative pillows. A glass coffee table sits atop a patterned rug, complemented by a lamp and a small plant. The staircase leads to an upper level, with a wall map artwork enhancing the space.

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

FamilyKitchenComfort

4.9 out of 5 average rating, 396 reviews

4.99 out of 5 average rating, 144 reviews

A charming cottage is framed by lush greenery and colorful flower planters. The white exterior features multiple windows, allowing ample natural light. A welcoming front porch leads to the entrance, adorned with patriotic bunting, inviting guests to enjoy the serene surroundings.

Cottage in Barrington

Cozy French Inspired Cottage in rural setting

Relax and escape to our charming, one of a kind cottage. Beautifully decorated with period furniture and tastefully updated with modern amenities. The cottage offers slate tile and hardwood floors. Original pine floors line the upstairs loft bedrooms. Cook in a French inspired country kitchen with butcher block counter tops. Rural setting, yet minutes away from everything! Downtown is a 20 min. walk and the Metra will take you to the city in 45 minutes!

KitchenFamilyAccess

4.89 out of 5 average rating, 120 reviews

Game Room & Fenced Yard Near O’Hare

Family-friendly vacation rental with modern amenities! ★ Can sleep 5 people ★ 3 Bedrooms, 4 beds ★ Rest peacefully in a king-size bed ★ Watch your favorite shows on a 65" 4K TV ★ Stay connected with fast Wi-Fi. ★ Convenient private driveway. Visit Waterworks Park (4 mins) Woodfield Mall (10 mins) Medieval Times (12 mins) Legoland (14 mins) Schaumburg Convention Center (15 mins) Numerous dining options nearby. Book today and create lasting memories!

FamilyKitchenLayout

4.9 out of 5 average rating, 184 reviews

The exterior of a two-story home is depicted, featuring a combination of white and black siding. A prominent bay window enhances the facade, while landscaped flower beds with red mulch and small plants frame the entrance. Green grass and a sidewalk lead up to the house.

Home in Des Plains

Cozy Home by O'Hare + EV Plug

Family-friendly 3BR/2BA home in Des Plaines! Enjoy arcade games, board games, and an EV charger. Nestled in a quiet neighborhood near parks, shopping, and entertainment. Just minutes from Des Plaines Theatre, Rivers Casino, Mystic Waters, and Fashion Outlets of Chicago. Ideal for families or groups seeking comfort, fun, and convenience with easy access to top attractions and O'Hare Airport. Your perfect home base for exploring the Chicago area!

FamilyIndoor spacesCheck-in

The exterior of a modern ranch-style home is showcased, featuring a strategic arrangement of greenery and colorful landscaping. A paved driveway leads to a welcoming entrance, flanked by two garage doors. The home is complemented by a clear blue sky and mature trees in the background.

4.93 out of 5 average rating, 102 reviews

Cozy Schaumburg 5 br/3.5ba w/ bonus rooms/office

Luxurious–Cozy Ranch Stunning 5-bedroom, 3.5-bath home offers spacious modern living on a quiet cul-de-sac. The home features a gourmet kitchen with a Viking 48” stove and Omega cabinets, a master suite with a coffee bar, his-and-hers bathrooms, and a jacuzzi tub. Enjoy two fireplaces, three wet bars, and a basement with a pool table, arcade games, an 85” TV, and a kids' playroom. Outside, the backyard has a patio, gazebo, and firepit.

Indoor spacesFamilyBackyard

Superhost

A stylish living room features a comfortable gray sofa adorned with colorful cushions. A round coffee table sits in front, complemented by a unique wooden chair and playful orange poufs. Large windows allow natural light, while a decorative mural of angel wings graces the dark feature wall.

4.88 out of 5 average rating, 140 reviews

InstaWorthy! Modern Gem, Perfect Family Getaway-Pe

Have fun with the whole family at this stylish place! - Minutes away from Woodfield Mall, Legoland Waterworks Indoor Water Park, Golf, Outdoors, and more! - Private Driveway - Blazing Fast 1GB internet speed - 60 4K Smart TV w/ Roku Live TV - Pack n Play, High Chair, Stroller - Stocked Kitchen with Coffee and Waffle Bar! - Outdoor Patio Area w/ games - Working Desk Area. - Firepit, Corn Hole, Pool Table - King Size Bed in Main

FamilyKitchenGetting around