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House vacation rentals in Kendall County

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Top-rated house rentals in Kendall County

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A bright and airy attic space is presented, featuring a spacious bed with a red coverlet. Decorative pillows add color to a cozy seating area with a dark sofa. Overhead fans complement the pleasing ambiance, and a kitchenette is subtly integrated in the background.

Home in Yorkville

5 out of 5 average rating, 4 reviews

3BR Retreat in a House 2Floor

Welcome to your peaceful 3BR retreat! Nested in a tranquil rural setting yet close to Raging Waves and Greater Chicago Area. This sun-filled 2nd floor unit offers Artsy Romantic style w nature views. Enjoy a private entrance, balcony overlooking a fruit garden, cozy kitchenette, elegant décor, workstations in every room! Perfect for families, couples, or small groups. For your romantic mood we got 4 U Smart RGB Lights & Smart Lights & Music in the Bathroom. Breed Deeper, Rest Better, have Fun!

A serene creek flows through a lush green landscape, surrounded by trees with budding leaves. In the background, a house is partially visible amid the foliage, creating a peaceful natural setting.

Little Rock Woods Retreat

Escape from it all at our tranquil getaway in the woods. Wander the trails exploring nature on this 26 Acre wooded property, including 1000 ft of frontage along Little Rock Creek. Gather with family & friends for a BBQ on the large screened porch and adjoining deck, play bags or shoot hoops in the spacious yard or just enjoy watching the wildlife and listening to the owls hooting back & forth. With 2 kitchens and 2 laundry areas, smart TVs throughout this is the ideal spot for family gatherings

A spacious master bedroom features a large bed with a neutral-coloured duvet, accompanied by decorative pillows. A ceiling fan provides ventilation, and natural light filters through sheer curtains. A cozy chair offers additional seating, with framed art adorning the walls.

4.89 out of 5 average rating, 168 reviews

Large Family Home w/Garage-King beds, Fast Wi-Fi

Relax and enjoy this open, well lit piece of suburbia designed and furnished to be the fully outfitted home away from home. Before every reservation this home is throughly cleaned and given ozone and UV treatment to sanitize. This home includes amenities like the fire pit and grill on the back porch, the 2 car garage, and a finished basement with a ping pong table and PlayStation. Particular favorites also include the fully outfitted kitchen, and the large master bedroom with a private bath.

A spacious living area is presented with a large, U-shaped sectional sofa and a matching armchair. A coffee table sits in the center, complemented by light hardwood floors and a patterned area rug. Natural light filters through a nearby dining space, featuring a table set for meals.

Home in Montgomery

5 out of 5 average rating, 6 reviews

5 bdrm/2.5 bth/Fenced Yard/Quiet St /Pet friendly

Escape with your family at this tranquil retreat, nestled in the heart of Montgomery near highways 34 and 25. Situated on a quiet street, this spacious home boasts five bedrooms, ensuring ample space for everyone. The master bedroom features a queen-size bed and en-suite bathroom, other bedrooms offer: queen bed, full-size bed, twin bed with twin bed trundle, and the last bedroom offers a bunk bed. The property also has a fenced yard with a patio, ideal for outdoor entertaining & relaxation.

A spacious brick home with a steeply pitched roof is framed by manicured lawns and vibrant trees. The front of the house features large windows and an inviting entryway, along with two garage doors. A clear blue sky enhances the home's bright exterior.

Home in Plainfield

4.94 out of 5 average rating, 54 reviews

WATER FRONT LUXURY HOME WILL FEEL LIKE A RESORT!

LUXURY HOME WITH A SPECTACULAR VIEW OF THE WATER. EXECUTIVE BRICK HOME WITH BRAZILIAN CHERRY-HARD WOOD FLOORS. FLOOR TO CEILING WINDOWS IN FAMILY ROOM WITH 14' CEILINGS/DECORATIVE BRICK FIREPLACE. GOURMET KITCHEN W/ MAPLE CABINETS/GRANITE & SS APPS/EATING ISLAND. SUNROOM WITH BEAUTIFUL VIEW OF POND. LUXURY MASTER SUITE W/ LUXURY BATH. FULL FINISHED BASEMENT WITH 9' FOOT CEILINGS INC FULL BATH & BED. TRANQUIL BRICK PAVER PATIO. (Plus 100-acre park, paths, soccer & baseball fields, & more).

A spacious living area is arranged with a dark sectional sofa and two accent chairs. A wooden coffee table is positioned in front, adorned with a bowl of greenery. Large windows allow natural light to fill the room, complemented by neutral-toned curtains and modern decor.

4.63 out of 5 average rating, 8 reviews

Your Unique Stay by the Tracks | LCP Collection

Our cozy home offers charm, comfort, and a touch of adventure! Located in Oswego, it’s perfect for relaxing or exploring. Here’s the fun part—you’re right by a railroad track! Occasionally, you’ll hear the friendly rumble of a passing train. Think of it as a cheerful wave from the conductor! We’ve added sound machines to keep things peaceful, and most guests say it adds charm to their stay. Also enjoy our game room with a classic Arcade Game! Hop aboard and book your unique getaway today!

A single-story ranch home is presented with a dark blue exterior and white shutters. A neatly trimmed lawn and concrete pathway lead to the front door. Flanking the entrance, small shrubs add greenery, while a tall evergreen tree stands nearby.

Home in Montgomery

4.86 out of 5 average rating, 145 reviews

Nice, Private Ranch Home

Nice private ranch home in a quiet neighborhood. Fox River and the river bike trail are only 3 minutes away, Rush Copley Medical Center, lots of shopping and dining options within minutes, Phillips park zoo, and water park very close, major roadways to Chicago. 10 min, from downtown Aurora where you can find the Hollywood Casino, Paramount theatre, many shopping stores and you can enjoy a walk along the Fox river, Fox valley mall and the Chicago premium outlets mall are only 20min away.

A spacious living room features a soft, light-colored sofa adorned with nature-themed cushions. A coffee table sits in front of the sofa on a patterned rug. A large window allows natural light to fill the room, complemented by wall art depicting an elephant in a forest.

Home in Montgomery

4.89 out of 5 average rating, 35 reviews

Quiet area/Petfriendly/Wi-fi/5 beds/1.5 bath

Discover a unique jungle-inspired getaway in a quiet, spacious neighborhood. Perfect for families and pet lovers, this home features a fenced backyard with a BBQ and outdoor seating for relaxation. Enjoy nearby activities such as fishing, a water park, parks, a zoo, scenic trails, go-karts, golfing, mini golf, and shopping just minutes away. Key Details ★Pets Welcome (ck rules) ★Free Driveway Parking (no garage access) ★No Parties, Events, Smoking, or Vaping Indoors ★60 mins to Chicago

A spacious living room features a large sectional sofa and two blue upholstered chairs, arranged around a black coffee table on a light area rug. A flat-screen TV is mounted on the wall, flanked by shelves with decorative items. Natural light enters through large windows with sheer curtains.

4.89 out of 5 average rating, 130 reviews

Cozy 4-bedroom ranch - minutes from everything

Relax and have fun with the whole family at this peaceful place to stay. It is located within walking distance from US Route 34 in the middle of shopping centers such as Meijer, Jewels, Target, Walmart, great restaurants, bars, entertainment, hair and nail salons, gas stations, etc. There are 5 beds (1 king and 4 queens plus a queen-size air mattress and a twin pull-out bed) and 3 couches waiting for their guests. The house is cleaned and sanitized before every reservation.

A spacious living room is highlighted by a large, ornate mirror above a classic fireplace. Soft gray carpeting covers the floor, and two tall windows provide natural light, framed by elegant drapes. A comfortable sectional sofa and a wooden TV stand complete the inviting space.

5 Bedroom Home and Private Woods

Welcome to Oakberry, a luxurious country estate nestled on a picturesque hill within 8+ acres of pristine forest, just minutes from Oswego. This serene retreat offers a blend of natural beauty and modern comfort. Recently renovated, this home offers contemporary conveniences with the timeless character of its 19th-century craftsmanship. Immerse yourself in nature's tranquility while enjoying the elegance of this unique home. Your dream getaway awaits—welcome to Oakberry!

A comfortable living room is shown with a gray sofa and armchairs arranged around a dark coffee table. Natural light fills the space through two large windows. A flat-screen TV is positioned on a media console, complementing the modern decor.

5 out of 5 average rating, 4 reviews

Aurora Rental - Shiloh

2200 SF unit is 15 min away from Chicago Premium Outlets - a discount mall, and I-88 which take you straight downtown. This property has 3 bedrooms, & 2.5 bathrooms. Master suite has a King bed, and 2 bedrooms has a Queen. The basement has a private area with a day bed, featuring 2 Twin mattresses! The living room has room for 1 air mattress (Total of 6 beds). Plenty of Kitchen utensils, including cooking spices and oils! Children friendly & lots of technology.

A charming bungalow exterior is adorned with vibrant decorations, including red lanterns and festive displays. The porch features white railings and blooming planters, providing a welcoming atmosphere. A pathway leads to the front door, framed by greenery and a grassy lawn.

Quaint Oswego Downtown Bungalow

Enjoy Staying at this Downtown Oswego Charming Bungalow . Downtown Oswego .3 M Event Centers Venue 5126 - 2 M Norfolk Farm Weddings - 6.2 M Ashley Farm Events - 6.7 M Bear Cave Lake Events 4.4 M Fox River Trail - .4 M River Edge Park - 6.2 Miles Caterpillar Corporate - Montgomery 2.5 M (Interns/Rotations Welcome) Hospitals within 14 Miles Travel Clinicians Welcome! Rush-Copley Hospital Edwards Hospital Mercy Hospital Delnor Hospital

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Kendall County house rentals

Free parking on premises

Air conditioning

House rentals with a pool

A private inground pool is surrounded by a spacious patio featuring multiple lounge chairs. The pool is marked with depth indicators, showcasing its range from 3 feet to 5 feet. Lush greenery and a white fence provide a serene atmosphere, with a shaded blue umbrella positioned nearby.

4.93 out of 5 average rating, 76 reviews

Ottawa Oasis. Billiards. Pool. King Bed!

A spacious living area is characterized by a plush gray sofa and a round coffee table. Decorative wall elements and a vibrant red holiday tree enhance the modern decor. Soft lighting is provided by a statement chandelier hanging from the ceiling.

Home in Glen Ellyn

4.78 out of 5 average rating, 18 reviews

Pardizes Suites

A charming two-story house is depicted, featuring a blue exterior with white trim and large windows. The front porch offers a welcoming entrance, while the backdrop showcases a marina with numerous boats docked on calm waters.

5 out of 5 average rating, 3 reviews

The Lookout at Heritage Harbor

A swimming pool is seen surrounded by a white fence, with colorful pool floats inviting fun. Sunlight reflects off the clear blue water, and lush green trees provide a natural backdrop. A patterned mat lies at the edge, enhancing the relaxing atmosphere.

Home in Glen Ellyn

4.95 out of 5 average rating, 20 reviews

Glen Ellyn Home

A porch area offers a view of the calm harbor, featuring several boats moored along the water's edge. Two comfortable chairs with blue cushions sit on the wooden deck, inviting relaxation. Green grass extends towards the water, with trees lining the distant shore under a clear sky.

4.67 out of 5 average rating, 6 reviews

Harbor Inn- Ship, Captain, Crew

An expansive outdoor space showcases a landscaped backyard with an in-ground pool, surrounded by a protective fence. Loungers are positioned around the pool, and a covered seating area is visible, providing shaded relaxation options. Nearby, a well-maintained lawn extends into the background.

Home in Plainfield

4.76 out of 5 average rating, 45 reviews

30 mins to CHI• 3 Kings• BBQ Grill• Spacious• Pool

A charming two-story lake house is highlighted, featuring a light gray exterior and white railings. The property includes a spacious porch on the upper level. Lush green landscaping surrounds the home, with well-maintained shrubs and a clear pathway leading to the entrance.

4.62 out of 5 average rating, 13 reviews

Casa Azul

4.5 out of 5 average rating, 6 reviews

Celebrate at Hacjenda house

Weekly house rentals

A spacious living area is presented with a large, U-shaped sectional sofa and a matching armchair. A coffee table sits in the center, complemented by light hardwood floors and a patterned area rug. Natural light filters through a nearby dining space, featuring a table set for meals.

Home in Montgomery

5 out of 5 average rating, 6 reviews

5 bdrm/2.5 bth/Fenced Yard/Quiet St /Pet friendly

A spacious living area is arranged with a dark sectional sofa and two accent chairs. A wooden coffee table is positioned in front, adorned with a bowl of greenery. Large windows allow natural light to fill the room, complemented by neutral-toned curtains and modern decor.

4.63 out of 5 average rating, 8 reviews

Your Unique Stay by the Tracks | LCP Collection

A spacious open living area features a cozy sitting arrangement with two cream-colored chairs and an orange sofa. A large kitchen island with seating overlooks the room, while a modern fireplace adds warmth to the ambiance. Natural light brightens the space through large windows.

4.79 out of 5 average rating, 80 reviews

Moxie - w/ Game Room- 4 Kings, Sleeps 15

Top guest favorite

The cozy blue house is surrounded by vibrant autumn foliage, featuring a newly built wooden porch that offers views of the seasonal colors. A lawn covered with fallen leaves enhances the picturesque setting, inviting a sense of tranquility.

Home in Yorkville

4.99 out of 5 average rating, 72 reviews

Patriotic Cottage on the Hill

A spacious two-story brick home features a symmetrical façade with multiple windows, providing ample natural light. A well-maintained front yard is bordered by lush greenery, while a large driveway leads to two garages, enhancing the home's accessibility.

5 out of 5 average rating, 17 reviews

Serene 5-Bedroom Retreat, Oswego

A spacious master bedroom features a large bed with a neutral-coloured duvet, accompanied by decorative pillows. A ceiling fan provides ventilation, and natural light filters through sheer curtains. A cozy chair offers additional seating, with framed art adorning the walls.

4.89 out of 5 average rating, 168 reviews

Large Family Home w/Garage-King beds, Fast Wi-Fi

A hot tub is nestled under a metal canopy, offering privacy with curtains that can be drawn. Steps lead up to the tub, surrounded by a concrete patio. Fallen leaves lay on the grass nearby, contributing to the serene outdoor setting.

Home in Montgomery

4.81 out of 5 average rating, 54 reviews

Skip the hotel! Relax here!

A spacious living room features a large sectional sofa and two blue upholstered chairs, arranged around a black coffee table on a light area rug. A flat-screen TV is mounted on the wall, flanked by shelves with decorative items. Natural light enters through large windows with sheer curtains.

4.89 out of 5 average rating, 130 reviews

Cozy 4-bedroom ranch - minutes from everything

Private house rentals

A spacious living area is presented with a large, U-shaped sectional sofa and a matching armchair. A coffee table sits in the center, complemented by light hardwood floors and a patterned area rug. Natural light filters through a nearby dining space, featuring a table set for meals.

Home in Montgomery

5 out of 5 average rating, 6 reviews

5 bdrm/2.5 bth/Fenced Yard/Quiet St /Pet friendly

A spacious living area is arranged with a dark sectional sofa and two accent chairs. A wooden coffee table is positioned in front, adorned with a bowl of greenery. Large windows allow natural light to fill the room, complemented by neutral-toned curtains and modern decor.

4.63 out of 5 average rating, 8 reviews

Your Unique Stay by the Tracks | LCP Collection

A spacious open living area features a cozy sitting arrangement with two cream-colored chairs and an orange sofa. A large kitchen island with seating overlooks the room, while a modern fireplace adds warmth to the ambiance. Natural light brightens the space through large windows.

4.79 out of 5 average rating, 80 reviews

Moxie - w/ Game Room- 4 Kings, Sleeps 15

Top guest favorite

The cozy blue house is surrounded by vibrant autumn foliage, featuring a newly built wooden porch that offers views of the seasonal colors. A lawn covered with fallen leaves enhances the picturesque setting, inviting a sense of tranquility.

Home in Yorkville

4.99 out of 5 average rating, 72 reviews

Patriotic Cottage on the Hill

A spacious two-story brick home features a symmetrical façade with multiple windows, providing ample natural light. A well-maintained front yard is bordered by lush greenery, while a large driveway leads to two garages, enhancing the home's accessibility.

5 out of 5 average rating, 17 reviews

Serene 5-Bedroom Retreat, Oswego

A spacious master bedroom features a large bed with a neutral-coloured duvet, accompanied by decorative pillows. A ceiling fan provides ventilation, and natural light filters through sheer curtains. A cozy chair offers additional seating, with framed art adorning the walls.

4.89 out of 5 average rating, 168 reviews

Large Family Home w/Garage-King beds, Fast Wi-Fi

A hot tub is nestled under a metal canopy, offering privacy with curtains that can be drawn. Steps lead up to the tub, surrounded by a concrete patio. Fallen leaves lay on the grass nearby, contributing to the serene outdoor setting.

Home in Montgomery

4.81 out of 5 average rating, 54 reviews

Skip the hotel! Relax here!

A spacious living room features a large sectional sofa and two blue upholstered chairs, arranged around a black coffee table on a light area rug. A flat-screen TV is mounted on the wall, flanked by shelves with decorative items. Natural light enters through large windows with sheer curtains.

4.89 out of 5 average rating, 130 reviews

Cozy 4-bedroom ranch - minutes from everything

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