Vacation rentals in Kendall County

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Top-rated vacation rentals in Kendall County

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Guest favorite
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
4.86 out of 5 average rating, 29 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!

Top guest favorite
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.
Home in Plano
5 out of 5 average rating, 9 reviews

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

Guest favorite
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.
Home in Aurora
4.9 out of 5 average rating, 177 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.

Top guest favorite
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, 16 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.

Guest favorite
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
4.87 out of 5 average rating, 155 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.

Guest favorite
A wooden deck furnishes an outdoor dining area with a large table and chairs, set against a backdrop of lush greenery and expansive views of the river. The tranquil water glistens in the sunlight, bordered by trees that enhance the natural setting.
Home in Plano
4.9 out of 5 average rating, 41 reviews

Retreat on Fox River w/ Stunning Views & Hot Tub!

Experience the ultimate riverfront getaway at this stunning home that sets the standard for luxury and elegance along the Fox River. The interior spans 6,300+ sq. ft. across 3 levels of impeccably designed space and features 7 bedrooms, 6 king-size beds, and 4.5 baths to comfortably accommodate up to 16 guests. Set on over 2 acres of wooded grounds, the estate features a long list of luxe amenities including a dock, hot tub, fire pit, 2 kitchens, entertainment room & parking for 10 cars.

Guest favorite
A spacious room is highlighted by a patterned bedspread on a comfortable bed, with a wooden headboard. A flat-screen television is mounted on the wall, and a small kitchen area with bar stools is visible. Natural light enters through a window, enhancing the inviting space.
Guesthouse in Oswego
4.91 out of 5 average rating, 107 reviews

The Loft-Rustic Retreat and Sauna

This unique space features a beautiful relaxing yard space and easy walking distance to downtown Oswego.. If you need a place to work quietly or stay overnight this is the ideal location to get rest and relaxation, as well as, enjoy the local tranquilities. Antique shopping, River adventures, Bike trails, and more! The Fox River Trail is a few blocks from the Loft and goes North all of the way up to Algonquin. Along the trail is the River where you can tube, kayak, canoe, fish…

Superhost
A light-filled living area is presented with a soft blue couch and a glass coffee table atop a textured rug. A comfortable armchair complements the seating arrangement. French doors lead to an outdoor deck, enhancing the connection with nature.
Townhouse in Yorkville
4.79 out of 5 average rating, 154 reviews

Riverfront Townhome in Downtown Yorkville

➢ Everything is sanitized/washed/cleaned after every guest ➢ Right on Fox river ➢ Raging Waves Waterpark - 4.1mi ➢ Yak Shack (Canoe & kayak rental) - 0.8mi ➢ Saw Wee Kee Park - 6mi ➢ Fast, Dedicated Wifi ➢ Free parking in attached garage for 2 compact-size cars + additional free parking onsite. ➢ 3 Smart TVs (Living Room, Bedrooms) ➢ Fully equipped + stocked kitchen / bathroom / laundry ➢ Located Downtown Yorkville ➢ Pack 'n Play ➢ High chair ➢ Kurig coffee maker ➢ King size beds

Guest favorite
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.
Home in Oswego
4.9 out of 5 average rating, 136 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.

Home in Montgomery
4.86 out of 5 average rating, 7 reviews

Charming 2-Bedroom Duplex with Modern Amenities

1100 SF unit is 15 min away from Chicago Premium Outlets - a discount mall, and I-88 which take you straight downtown. This property has 2 bedrooms, &.1 bathrooms. Master suite has a King bed, and 2nd bedroom has a Double bed. The living room has room for 1 air mattress. Plenty of Kitchen utensils, including cooking spices and oils! Children friendly & lots of technology. The space Nice sized home, with 1 car garage parking, driveway, and public parking.

Top guest favorite
A functional kitchen area features wooden cabinetry and modern appliances. Ample countertop space is complemented by tile flooring. A small dining table with chairs is positioned near a window, allowing natural light to illuminate the space. A doorway leads to a cozy bedroom.
Guest suite in Oswego
4.96 out of 5 average rating, 72 reviews

1 Bed w/ Full Kitchen A Mile From Downtown Oswego

Enjoy a stay within walking distance of 3 parks and about a mile from downtown Oswego and its quaint shopping area. Nestled in the middle of a great neighborhood, you'll feel safe and be able to enjoy a quick getaway or an extended stay. If you're interested in visiting Chicago, we're close enough for day trips to the city (about 45 miles) but far enough to save some money. You'll definitely have a great time here!

Top guest favorite
A stone fire pit is surrounded by seating, with a crackling fire at its center. The serene Fox River is visible in the background, framed by lush greenery. Two chairs and a small table are positioned nearby, providing a comfortable area for relaxation.
Cottage in Plano
5 out of 5 average rating, 14 reviews

Fox River House

Relax with your family and friends at this peaceful place! Enjoy beautiful Fox River in the back yard! The house is minutes away from downtown Yorkville, Raging Waves Waterpark and right next to beautiful Silver Springs park. There are ton of fun activities and places to explore around! The nearby towns offer great restaurants and events. We provide the firewood for your stay!

Popular amenities for Kendall County vacation rentals