Holiday rentals with a fireplace in Kendall County

Private Riverfront: Kayak-Fire Pit-Near Water Park

Escape to a peaceful riverfront retreat on over half an acre with beautiful water views! Ideal for families, couples, or those working in the area, the home offers wildlife sightings, a cozy fireplace, fire pit, and game room with Nintendo Switch. Watch the sunrise or full moon rise from a beautiful patio. Private chef, sound healing yoga, private driver, and kayak rentals are available upon request for an additional fee. Golf, dining, shopping, and Illinois’ largest water park are minutes away.

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

Private Pickleball Court, Seats for All, See Deer

Arrive under the trees, soak in the quiet, and watch deer while you sip a hot beverage from the coffee bar. At Deer Run Lodge, you get two fully equipped homes connected by a sunroom—space to gather when you want, and privacy when you need. Spend the day playing pickleball on the regulation court, grill on the deck, soak in 2 hot tubs, then end by the fire pit beneath the stars. Though it feels secluded, you’re minutes from restaurants, the Fox River, and less than 15 minutes from Raging Waves.

5 bdrm 7 bed 2.5 bth Ranch w Fenced Yard Sleeps 10

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.

Yorkville private room 1

"Yorkville Private Room is great for couples, solo adventurers, and business travelers. Experience the comfortable and casual vibe. Room 1 is a private room with a shared bathroom for up to 2 guests. It is one of our brightest rooms. Our place offers a unique blend of comfort and charm, making it truly special. Nestled in a serene location, it is perfect for relaxation and rejuvenation. Whether you're here for a getaway or a special occasion, our place promises an unforgettable experience."

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!

Yorkville private room 3

Yorkville Private Room is great for couples, solo adventurers, and business travelers. Experience the comfortable and casual vibe. Room 3 is a private room with a shared bathroom for up to 2 guests. It is one of our brightest rooms. Our place offers a unique blend of comfort and charm, making it truly special. Nestled in a serene location, it is perfect for relaxation and rejuvenation. Whether you're here for a getaway or a special occasion, our place promises an unforgettable experience.

Luxury private River Cabin retreat with zipline

Escape to this modern riverfront cabin surrounded by mature trees and peaceful nature. Enjoy private river access, complimentary kayaks, and an exciting zipline adventures. Relax by the river, explore the area, or simply unwind in a serene setting. You'll feel miles away from it all while still being just minutes from restaurants, grocery stores, bars, and local attractions. Perfect for couples, families, and friends seeking a unique blend of comfort, adventure, and relaxation.

Wooded Oasis: Pickleball, Hot Tub, Corn Hole, Pets

Wake to birdsong, a deer or two grazing at the tree line, and your first cup from the coffee bar on the private deck. Soak in the hot tub, grill lunch, and end the day by the fire while stars peek through the trees. When you want to explore, you’re minutes from the Fox River, Raging Waves, Silver Springs State Park, the Marge Cline Whitewater Course, and mountain biking at Saw WeeKee Park—then it’s back to your quiet, wooded hideaway.

Log Cabin Oasis: Pickleball, Hot Tub, Deer, Pets

Visitors call Deer Run Lodge “a hidden gem,” “peaceful and spotless,” and “the perfect mix of rustic and modern.”They mention seeing deer every day, super-comfy beds, thoughtful touches, and wonderful, responsive hosts. Whether you’re planning a family weekend, couples’ retreat, or friends’ getaway, this cabin delivers relaxation, comfort, and a front-row seat to nature’s quiet magic.

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!

Luxury Riverfront Retreat w/ Game Room + Fire Pit

Welcome to Dovehill, a luxury riverfront escape where comfort, connection, and adventure meet. Perfect for families, friends, and group getaways, this elegant 3-bedroom, 3-bath home offers direct access to the Fox River, resort-style amenities, and expansive outdoor living — all set against the peaceful backdrop of nature.