Family-friendly vacation rentals in Matteson

4.99 out of 5 average rating, 528 reviews

A charming, rustic cabin is nestled among vibrant autumn foliage, showcasing a wooden exterior and a sloped metal roof. The cabin is partially obscured by trees, with golden leaves creating a warm frame around the structure, signaling a serene woodland retreat.

Farm stay in La Porte

Cabin on Swede Hill

Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

4.92 out of 5 average rating, 114 reviews

A vibrant garden area is filled with a variety of lush green plants and colorful flowers. Stone elements lead to a small water feature, surrounded by dense foliage. The peaceful setting offers a natural retreat, inviting exploration or relaxation.

Apartment in Homewood

Charming Garden Apartment

Make yourself at home in a charming apartment with all the amenities! Lose yourself birding or reading a book surrounded by lush gardens. Take a short walk to downtown Homewood to enjoy shopping & dining or catch the train to Chicago. 🏳️‍🌈 BLM Safe space! After a day of exploring, a king-sized sleep number bed & lush bathroom features will pamper you! A fold-down sofa creates an additional bed. Dogs welcome! This suite has a kitchenette with a convection toaster oven & induction cooktop.

4.94 out of 5 average rating, 868 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 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!

4.94 out of 5 average rating, 150 reviews

A cozy tiny home is situated beside vibrant organic vegetable fields, showcasing rows of leafy greens. The home features a combination of rustic wood and modern metal siding, with large windows and a welcoming porch area that includes chairs for outdoor relaxation.

Tiny home in De Motte

Tiny Home on Organic Veggie Farm

Place yourself right in the beauty of the land and nature in this cozy tiny home at Perkins' Good Earth Farm. The tiny home has a loft bedroom, bathroom with shower and composting toilet, kitchen, sitting area, and deck. You'll be surrounded by organic vegetable fields, 11 acres of woods, walking trails--and within perfect view of both the sunrise and sunset. You'll also have easy access to our farm store where you'll find fresh fruits & veggies, homemade soups & salads and so much more.

4.94 out of 5 average rating, 275 reviews

A welcoming open concept living space is portrayed, featuring a comfortable sofa with decorative pillows. A dining area with a table for six sits adjacent to a kitchen with modern appliances. A functioning fireplace adds charm, while a large TV is mounted on the wall.

Home in Manteno

Manteno Luxury Comfy Cozy home with- 2 king beds!

6 minutes from I-57 expressway. Nestled in a cul-de-sac, this open concept 2 bedroom 2 bath townhome! There is a fireplace, dining room and convenient patio with sliding glass doors that lead to the outdoor patio The home is comes with wood floors & stainless steel appliances in the kitchen. Kitchen is fully stocked for cooking. Bedrooms have a 55" Smart TV for your enjoyment! The living room has a 65" Smart TV . We also have a queen size electric airbed with extra pillows & linens.

4.89 out of 5 average rating, 108 reviews

A single-story home features a welcoming front porch with seating, surrounded by a well-maintained lawn. The exterior displays a mix of brick and light-colored siding, complemented by neatly arranged shrubs and seasonal decorations. A spacious driveway leads to a single-car garage.

Home in Bradley

Cheerful 3 Bedroom, 2.5 bath central Bradley Home

A GREAT HOME AWAY FROM HOME! Conveniently located in central Bradley's family friendly Blatt Subdivision. Home sleeps six guests. 3 bedrooms, 2 queen and 2 twin beds. 2.5 bathrooms including a tub and a walk-in shower, complete with linens, toiletries and hair dryer. Additional features include a large kitchen with cooking accessories, air fryer and some essential condiments including coffee. Fenced in yard, small patio and 2 car garage. Scan QR Code in photos for Virtual Tour.

4.96 out of 5 average rating, 102 reviews

Guest suite in Flossmoor

Fun game-room suite with hot tub & optional Yurt

Activities includes: PS5 Disc w/TV Xbox Series X w/TV Outdoor heated Jacuzzi 27' above ground pool Pool and Air hockey table Arcade machine with 12 games Life Size Connect 4 Board games Basketball machine Electric fire place Queen & full size beds Full size sofa pull out sleeper Gazebo with two twin beds (seasonal) Fresh Eggs with chickens seasonal Gas Grill-propane included Romantic Robe for 2 (in colder months must request) Event Yurt add on $225 up to 25 additional guest

Guest suite in Orland Park

A sitting room features a beige sofa and a cream-colored armchair, positioned near a wooden desk. Two lamps provide soft lighting, while several framed photographs and artwork adorn the walls. Large windows allow natural light to fill the space, complemented by neutral-colored carpeting.

4.98 out of 5 average rating, 124 reviews

Private Guest Suite 2 Cozy Rooms

Private guest suite with separate entrance. Sitting room, kitchenette, bedroom w/queen bed, private bath, plus twin sofa bed in sitting room. Great alternative to hotel for business trip or visiting the area. Conveniently located in southwest suburbs of Chicago, 40 minutes from downtown by car (non rush hour) or Metra lines a few miles from the house. Set near a golf course and forest preserve, nearby to multiple restaurant and shopping districts less than 10 minutes away.

4.95 out of 5 average rating, 218 reviews

A private cottage is surrounded by lush greenery and features a wooden deck adorned with several blue planters. Steps lead up to the entrance, which is framed by large windows allowing natural light to fill the interior.

Guesthouse in Valparaiso

Private Cottage in Gated Nudist Community

We offer a private cottage on the grounds of Lake O the Woods Club. Cottage has Queen size bed, air conditioning, heater, refrigerator, microwave, TV, coffee maker, work/dining area, private deck and porta-potty. Payment of club daily grounds fee ($30-$60) is optional . Pricing on club website. There is no running water in the cottage. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area after payment of grounds fees.

Guest suite in Crown Point

The exterior of a private guest house is shown, featuring a detached two-story structure. A driveway leads to a garage with a white door, while a wooden staircase ascends to the entryway. The surrounding area includes greenery and paved walkways.

4.94 out of 5 average rating, 271 reviews

IT'S THE WRIGHT PLACE

Private guest house newly remodeled. One bedroom queen bed, bath w/shower, full kitchen stocked, including microwave and Keurig coffee maker pods included, family room TV, and WIFI. No matter if you are in town for work, sport competition, family or just vacationing we offer all the comforts of home. Air Mattress available upon request. Please treat as your own home, follow all house rules. No party or gatherings. This is a no smoking home.

4.96 out of 5 average rating, 122 reviews

A spacious living area features a light-colored sectional sofa adorned with soft pillows, positioned beside a wooden coffee table. A decorative area rug adds warmth to the hardwood floor. Natural light enters through a window, complemented by dark curtains. A potted plant and lamps provide additional light.

Home in Munster

Your Quiet Oasis: Cozy & Private

Escape to this private 2-BR home, perfect for remote workers, cyclists & brewery fans! Enjoy a dedicated workspace with fast Wi-Fi (413 Mbps), a full kitchen, and a spacious, private backyard with a gas grill. This pet-friendly, single-level retreat is your convenient base for exploring nearby nature trails, 6 local breweries, and casinos. Comfortably fits small groups or families seeking a quiet getaway just 30 mins from Chicago.

4.98 out of 5 average rating, 247 reviews

Double doors open to a bright living area featuring a leather sofa and a light-colored armchair. A coffee table is placed on a soft area rug, while lamps provide soft illumination. A ceiling fan hangs above, and large windows allow natural light to fill the space.

Home in Manteno

Updated, bright, and modern, 3 bedroom home.

You will be comfortable in this newly remodeled three bedroom, two bathroom home. ✶ 6.7Miles to Olivet Nazarene University ✶ 8.4Miles to Riverside Medical ✶ 11Miles to Kankakee River State Park ✶ 43Miles to Midway Airport The home FEATURES: *Safe, quiet, walkable neighborhood *3 Bedroom; 1 King, 1 Queen, 2 twin beds *Spacious fully equipped kitchen with coffee station *Washing Machine, Dryer & Dishwasher * Fast Wi-Fi

Popular amenities for Matteson 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, 177 reviews

Couples Getaway, Jacuzzi, Sauna, Pool is Open

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, 474 reviews

Master qtr close to nature & easy urban facilities

4.96 out of 5 average rating, 233 reviews

The open living area features large floor-to-ceiling windows framing views of the surrounding woods. A sleek two-tone sofa and modern armchairs are arranged near a minimal table. Warm wooden flooring complements the contemporary design, and a staircase leads to the upper level.

Home in Beverly Shores

Secluded Modern Retreat Near Beach - "Sandlot"

4.94 out of 5 average rating, 151 reviews

The charming farmhouse features a two-story design with blue siding and white trim. Symmetrical windows adorned with shutters enhance the facade. A welcoming porch is visible, surrounded by landscaped greenery. The structure is situated on a quiet street, providing easy access to the surrounding area.

Home in Bourbonnais

The Blueberry, Steps from ONU #walk there #Hottub

4.99 out of 5 average rating, 155 reviews

A clear, geodesic dome is set on a paved patio surrounded by a grassy area and decorative plants. The backdrop features a tranquil lake and lush trees, illuminated by a colorful sunset sky.

Guesthouse in Valparaiso

Lakeside Dome Retreat w Hot Tub Near Indiana Dunes

A large hot tub is positioned in a well-maintained backyard, surrounded by lush trees. Nearby, a sandy firepit area is complemented by seated benches, while a swing set is visible towards the rear, all enclosed by a tall wooden fence.

4.92 out of 5 average rating, 123 reviews

Singing Sands Trl | Hot Tub Retreat | Dogs OK

4.86 out of 5 average rating, 177 reviews

A spacious spa room features a modern two-person jacuzzi, surrounded by elegant marble walls. The jacuzzi is designed with a clear accent panel, and amenities such as towels are neatly arranged nearby, promoting a calming and relaxing environment.

Home in Whiting

The Spa of Downtown Whiting

4.94 out of 5 average rating, 453 reviews

The tranquil surface of Flint Lake reflects a colorful sunset, with soft hues of pink and orange blending into the serene blue sky. The surrounding tree line is silhouetted against the fading light, creating a peaceful and calming atmosphere.

Cottage in Valparaiso

The Lake Escape -Cozy Lakefront Cottage Valparaiso

Family- and pet-friendly home rentals

Guest suite in Naperville

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.

4.96 out of 5 average rating, 534 reviews

Cozy Lakeview Studio with Private Access

4.95 out of 5 average rating, 241 reviews

The cabin's exterior is framed by colorful autumn foliage, with vibrant red leaves and dappled sunlight filtering through the surrounding trees. Stone steps lead to the entrance, enhancing the rustic charm of the well-maintained landscape.

Cabin in Michiana

Luxury Cabin Getaway •2 min to Beach• 1hr Chicago

4.92 out of 5 average rating, 139 reviews

A cozy living area features a light-colored sofa and a dark armchair, arranged around a wooden coffee table. A textured area rug lies beneath, and soft light is provided by a floor lamp. Large, partially draped windows allow natural light to enter.

Guesthouse in Evanston

Cozy Guesthouse near NU - next to Lee Street Beach

Superhost

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

4.87 out of 5 average rating, 169 reviews

Cozy House, Main Road Access, Close to Colleges

4.96 out of 5 average rating, 114 reviews

The open living area showcases a cozy seating arrangement with a brown sofa and modern chairs. A ceiling fan hangs above, and the space is illuminated by warm light from the nearby kitchen. A large TV is mounted on the wall opposite the seating area.

Home in Porter

Dunes Homestead - Near Dunes + Lake + Dog Friendly

Home in Country Club Hills

4.92 out of 5 average rating, 25 reviews

Cul De Sac Jacuzzi home | Near Chicago

Superhost

A well-maintained camper is set on a grassy area, featuring a wooden deck with colorful chairs. A hammock is strung between trees, inviting relaxation. The bright red awning provides shade, and a peaceful outdoor setting is framed by lush greenery.

Camper/RV in Chesterton

4.84 out of 5 average rating, 128 reviews

South Shore RV National Park.

4.87 out of 5 average rating, 140 reviews

A single-story house is presented with a well-kept front yard featuring green grass and a stone pathway leading to the entrance. The exterior is clad in white siding, with black shutters framing the windows. A small bench is placed on the porch, adding to the inviting appearance.

Home in Bourbonnais

Freshly Remodeled Bourbonnais Home

Family-friendly home rentals with a pool

4.93 out of 5 average rating, 91 reviews

Home in Schererville

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

The exterior of a multi-level house is depicted, featuring a combination of siding and stone accents. Large windows are present, along with balconies on the upper levels. A paved driveway leads to a garage, surrounded by greenery and a clear blue sky.

4.93 out of 5 average rating, 114 reviews

Beautiful home in Beachwalk/Notre Dame weekends

The charming two-story home features a wide front porch with ample seating and decorative lighting. White railings and a wooden design enhance its appeal. Flanking trees provide some greenery, and the entryway is welcoming with its open doors and stylish decor.

4.96 out of 5 average rating, 194 reviews

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Superhost

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

4.77 out of 5 average rating, 53 reviews

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

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.

4.93 out of 5 average rating, 111 reviews

Just remodeled apartment close to airport and mall

4.96 out of 5 average rating, 116 reviews

An open-concept living space is showcased, featuring modern kitchen appliances, a dining table with seating for six, and a comfortable sofa. Large windows allow natural light to fill the area, providing views of the outdoor landscape.

Condo in Evanston

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

5 out of 5 average rating, 11 reviews

The Glass House is situated amidst vibrant autumn foliage, showcasing a modern design with expansive glass walls and a stone façade. The surrounding lawn features fallen leaves and natural wooden elements, with outdoor seating options visible on the terrace.

Home in Valparaiso

A Glass House in a Gated Nudist Community

A vibrant yellow front door is complemented by stone exterior and a decorative statue. The private pool area features clear blue water, surrounded by loungers on a spacious deck. An indoor sitting area is arranged with green and yellow decor, large windows allow natural light to fill the space.