Holiday houses in Kendall County

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Top-rated holiday rentals in Kendall County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home in Yorkville

4.82 out of 5 average rating, 17 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!

Guest favourite

Home in Aurora

4.9 out of 5 average rating, 172 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 favourite

Home in Plainfield

4.95 out of 5 average rating, 56 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).

Superhost

Home in Oswego

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!

Guest favourite

Home in Montgomery

4.86 out of 5 average rating, 147 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 favourite

Home in Plano

4.91 out of 5 average rating, 35 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 favourite

Guesthouse in Oswego

4.91 out of 5 average rating, 106 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

Townhouse in Yorkville

4.79 out of 5 average rating, 153 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 favourite

Home in Oswego

4.89 out of 5 average rating, 132 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.

Guest favourite

Cabin in Yorkville

4.95 out of 5 average rating, 19 reviews

Log Cabin in Woods: 3 King Beds at Relaxing Oasis

Nestled in a wooded area, Deer Run Lodge Log Cabin offers a unique blend of seclusion and comfort, perfect for those seeking a tranquil getaway. This charming log cabin can comfortably accommodate up to 6 guests, featuring 3 bedrooms and 2 bathrooms. Area Activities: - Raging Waves - Fox River is perfect for water activities - Marge Cline Whitewater Course - Silver Springs State Park - Saw Wee Kee Park for mountain biking. Restaurants within a 5-20 minute drive.

Barn in Oswego

4.94 out of 5 average rating, 31 reviews

The GC Barn - Town & Country Escape

Welcome to this exceptional luxury residence—a unique blend of history and modern design. Once a dairy barn, it features high-end craftsmanship and a signature silo that honors its heritage. Please note: This home is not an event venue—maximum 20 registered guests. All vehicles must be parked in the driveway; no street parking allowed. This home is in a quiet residential area with longtime neighbors; we kindly ask that all house rules be respected.

Top Guest favourite

Guest suite in Oswego

4.96 out of 5 average rating, 67 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!