Family-friendly holiday rentals in Elgin

4.91 out of 5 average rating, 192 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.

Flat 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 spacesKitchenQuiet

4.99 out of 5 average rating, 120 reviews

A bright living area features a cozy sofa and an armchair, arranged around a small desk workspace. Sliding glass doors open to an outdoor patio area, allowing natural light to fill the room. Soft curtains frame the doors, enhancing the inviting atmosphere.

Flat in Elgin

Peaceful Elgin APT King Bed

Located in a sleepy suburban neighborhood, this freshly renovated apartment offers everything for a weekend getaway, business trip, or extended stay with a full kitchen, open living space & bedroom. Enjoy peace & nature while still being minutes away from restaurants, shopping, outdoor activities & all the Chicago suburbs have to offer. The Tipi BNB is a walkout lower-level basement APT that provides guests with the privacy and accessibility of a separate entrance and self check in/check out

FamilyKitchenCheck-in

5.0 out of 5 average rating, 119 reviews

A bright and open kitchen and dining area features a large island with seating and a dining table set for multiple guests. Modern appliances are visible in the background, along with stylish cabinetry. Natural light fills the space through large windows with sheer curtains.

Home in Geneva

Outdoor Oasis • Fire Pit • EV Charger • Near Town

Private office, high speed internet. EV Charger. Spacious,King Bed.Great outdoor space, fire pit, Indoor fireplace. Close to towns. Great weekend getaway. Great rate. Close to two beautiful parks, huge soccer field, water splash park, slide and swing and etc. Mins away from to the fox river trail. Less than 2 miles away from beautiful downtown Geneva, historic shopping district with over 160 specialty shops and restaurants. Less than 3 miles away from another beautiful downtown of St. Charles.

Indoor spacesFamilyAccuracy

4.94 out of 5 average rating, 895 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 spacesKitchenAccess

4.89 out of 5 average rating, 205 reviews

A spacious living area features a light-colored sectional sofa, accompanied by a decorative plant. A dining table is set nearby, and natural light enters through multiple windows. The space is complemented by a patterned area rug and a decorative wall art piece.

Home in Elgin

My Lagoon - 3 br Entire SF home Sleeps 8. King Bed

Welcome to your lagoon. An entire single family house boasting 3 bedrooms with a King bed, 2 queens and a Sofa bed. A true home away from home freshly renovated with tasteful modern coziness. 2 car garage w/ plenty of driveway space for 4 more. You are 25 mins from O'Hare Airport, 35 from the Epic Chicago Dwntwn. Stay Local? Plenty to do ! 10 mins to Now arena, 10 mins to Woodfield Mall, mins away is Villa Olivia, Arboretum, Main Event and more. Short Term, Keyless entry make yourself at home.

Indoor spacesFamilyQuiet

4.92 out of 5 average rating, 321 reviews

The image showcases a serene riverbank along the Fox River, with manicured green grass leading to the water's edge. Two decorative stone vases sit beside a paved area that meets the river, and trees line the opposite bank under a clear blue sky.

Home in South Elgin

Riverfront rental

Riverfront Rental Sits on a quiet street in downtown South Elgin. This home gives you complete access to the Fox River. The bedrooms are on the main level, along with a beautiful kitchen featuring cherry cabinets and an island with breakfast bar, and an awesome four-season porch overlooking the backyard and the beautiful river setting. The second-level loft has great natural light . Outside, you'll find concrete patio and walkway, and stairs leading down to the river and firepit. no pets

Indoor spacesFamilyTV

4.88 out of 5 average rating, 111 reviews

The exterior of a two-story home is displayed, featuring a spacious deck above the entrance. A well-maintained lawn surrounds the property, accented by trees and shrubbery. The driveway leads to a two-car garage, and a pathway leads towards the entrance of the house.

Home in Algonquin

On the Fox River Front/Sauna/Hot Tub/Kayaks/Grills

On Fox River in Algonquin Kick back and relax in this calm, tastefully finished space. Nestled amidst a picturesque waterfront and greenery, this stylish property exudes an elegance, harmoniously blending into the serene natural surroundings. It is a perfect combination of comfort and convenience. Located within a short range to fantastic "Old Town District" of Algonquin/superb restaurants, pubs, entertainment as well as parks and trails, simply just mere moments away from array of amenities.

Indoor spacesFamilyLocation

4.89 out of 5 average rating, 157 reviews

The exterior of a charming historic home features dark blue siding and a welcoming front porch with three steps leading up to the entrance. Large windows on either side of the door allow for natural light, while lush greenery surrounds the property, enhancing its curb appeal.

Home in Elgin

Charming Elgin Home with a Great Location

Come enjoy this beautifully restored and charming historic home from the early 1920s. Our place is good for couples, families or for a getaway with friends. Outdoor space with fully fenced backyard. This 2 bed 1 bath has been fully restored and is absolutely adorable! Walking distance to downtown Elgin (less than one mile) and Metra station (only one hour train ride into the city!), and less than 5 minute drive to I-90. Relax and get cozy in this adorable space.

FamilyKitchenAir conditioning

4.96 out of 5 average rating, 182 reviews

Home in Huntley

The Main Event Game House on the Huntley Square!

Step into the Main (Street) Event at The Huntley Square and experience a perfect fusion of historic charm and contemporary luxury. Our meticulously renovated 1920s gem, updated in 2023, promises an unforgettable getaway. Whether it's a special occasion or a gathering with loved ones, our Airbnb, located just one block from the delightful historic Huntley Square, offers endless activities. Explore the town or enjoy our expansive Main Event Game Enclave right at home!

FamilyKitchenWalkability

4.97 out of 5 average rating, 109 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!

Spacious 4BR/3BA modern home (2,082 sq ft) in Geneva—ideal for families, groups, and pets! Main-floor king suite perfect for mobility needs. Enjoy smart TVs in every bedroom, NEW dual zone HVAC Aug 2025, fast Wi-Fi, dedicated workspace, full kitchen with granite counters, washer/dryer, kid gear, and game options. Relax in the fenced backyard with fire pit and ample seating. Free driveway & street parking. Walk to downtown shops, Fox River Trail, wine bars, and more!

Indoor spacesKitchenGetting around

4.81 out of 5 average rating, 216 reviews

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

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.

Indoor spacesFamilyRiver

4.97 out of 5 average rating, 117 reviews

A charming blue house is situated in a spacious yard, surrounded by green grass and blooming white flowers. A stone pathway leads to a seating area with two chairs and a small table, framed by lush greenery and a wooden fence in the background.

Guest house in Elgin

Carriage House

This unique place has a style all its own. Completely renovated 1900 Carriage house . Originally a saloon and dance hall . Totally fenced and great play area for children and pets. The Little Blue House is on same property . It sleeps four and is also available for rent . I do not take guest without a five stay history.

FamilyIndoor spacesCleanliness

Popular amenities for Elgin family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.83 out of 5 average rating, 104 reviews

An outdoor deck overlooks the river, featuring a circular arrangement of comfortable chairs with decorative cushions. A fire pit is situated in the center, and a covered area with a hot tub is visible in the background, surrounded by lush greenery.

Home in St. Charles

THE RIVER HOUSE Water front! Hot Tub,Sauna!

KitchenFamilyValue

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

KitchenIndoor spacesCleanliness

4.9 out of 5 average rating, 230 reviews

Villa in Ringwood

Living the High Life Pool House

Indoor spacesKitchenCondition

4.91 out of 5 average rating, 143 reviews

Home in Montgomery

Skip the hotel! Relax here!

FamilyKitchenOutdoor spaces

4.92 out of 5 average rating, 294 reviews

Home in McHenry

River House with Deck and Hot Tub

FamilyKitchenAir conditioning

4.95 out of 5 average rating, 179 reviews

A spacious bathroom features large skylights that illuminate a freestanding tub, set beneath an arched window overlooking greenery. Two modern lounge chairs are situated nearby, enhancing the tranquil ambiance. The glass-enclosed shower and soft neutral tones create a serene and relaxing environment.

Farm stay in Harvard

Eden Farm: Family Stays & Intimate Moments

Indoor spacesFamilyLocation

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, 509 reviews

Master qtr close to nature & easy urban facilities

FamilyKitchenNearby

4.87 out of 5 average rating, 186 reviews

A modern living area features a sleek fireplace and large glass doors opening to a deck with lounge chairs overlooking the water. Sunlight shines through, creating a bright and airy feel, while the serene lake and surrounding greenery are visible outside.

Home in Twin Lakes

Cove at 420: Modern Lake Front Home near Chicago

Indoor spacesKitchenAir conditioning

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 109 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

KitchenIndoor spacesQuiet

4.91 out of 5 average rating, 313 reviews

An inviting coral front door featuring a bicycle-themed welcome sign. Two bright red mailboxes are mounted beside the door, complementing the cheerful color scheme. Light filters through a sheer curtain in the window above the door, enhancing the welcoming entryway.

Flat in St. Charles

Vintage Charm

Indoor spacesKitchenCondition

4.85 out of 5 average rating, 187 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

KitchenIndoor spacesWifi

4.94 out of 5 average rating, 122 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 spacesFamilyAmenities

4.94 out of 5 average rating, 136 reviews

The exterior of a Tudor-style home is displayed, featuring a combination of white stucco and dark wood accents. The building is complemented by a brick base, with steps leading to the front door. Lush greenery surrounds the structure, enhancing its charming appeal.

Flat in St. Charles

Tudor by the Fox- downtown St. Charles

KitchenFamilyLong stay

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.

4.9 out of 5 average rating, 395 reviews

a SIMPLE place

Indoor spacesKitchenHospitality

Guest suite in St. Charles

4.84 out of 5 average rating, 190 reviews

Cozy, Comfy, Close to Downtown

KitchenFamilyLayout

5.0 out of 5 average rating, 22 reviews

Home in Elgin

Quiet 3BR Home Next to Hospital w Fast WiFi

KitchenIndoor spacesLocation

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 238 reviews

A red sofa is positioned in front of a brick fireplace, creating a cozy seating area. A wooden coffee table is placed in front of the sofa. Soft lighting is cast from a lamp beside the sofa, and framed photographs adorn the walls.

Guest suite in Bartlett

Cozy & Spacious Suite in Quiet Neighborhood

FamilyIndoor spacesDecor

Apartment 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, 126 reviews

Just remodeled apartment close to airport and mall

FamilyIndoor spacesParking

4.9 out of 5 average rating, 101 reviews

The charming Victorian home features a welcoming front porch adorned with hanging flower baskets and a large American flag. A brick pathway leads through manicured hedges and colorful flower beds, enhancing the inviting outdoor space surrounded by mature trees.

Home in Woodstock

Grand 1800s Victorian Gem: Updated/by Downtown

FamilyIndoor spacesNearby

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

Game Room Suite with hot tub & Event Yurt up to 25

KitchenFamilyValue

4.89 out of 5 average rating, 132 reviews

An open kitchen area is showcased with a wooden dining table and two white chairs. Modern appliances, including a microwave and a decorative wall with floral wallpaper, add a touch of charm. An oversized clock hangs above, contributing to the inviting ambiance.

Apartment in Lake Geneva

LG Quaint Condo on Lakeshore Dr.

KitchenFamilyCleanliness

Cottage in Fontana-on-Geneva Lake

A vibrant pool area is surrounded by a spacious deck featuring lounge chairs and umbrellas. Guests can be seen enjoying the water, with the large building in the background showcasing expansive windows that invite natural light. The atmosphere is lively and welcoming.

4.98 out of 5 average rating, 116 reviews

Fontana, Wis, Lake Geneva 4bd 2.5ba Abbey Springs

KitchenIndoor spacesParking

4.98 out of 5 average rating, 172 reviews

An aerial view of a swimming pool surrounded by a spacious wooden deck. Six comfortable loungers are positioned around the pool, with additional seating areas visible. An umbrella-covered table is set for outdoor dining, harmonizing with the greenery in the yard.

Flat in Logan Square

Fun & cozy getaway w/POOL/game room/FREE parking

KitchenIndoor spacesCheck-in