Holiday rentals with a kayak in Illinois

Samson's Whitetail Mountain Lakeside Cabin

The rustic lakeside treehouse has two bedroom loft upstairs, one lower bedroom, amazing views of our private lake and an assortment of animals (deer, axis, fallow, elk, and rams) that roam freely on the gated property. Enjoy kayaking, fishing,or lounge around the lake. Plan a trip to Garden of the Gods, Jackson Falls, Tunnel Hill Trail or Shawnee National Forest finishing the evening roasting hotdogs around the fire. *No parties or events allowed during your stay. DOOR CODE SENT PRIOR TO ARRIVAL

Private Beach • Lakefront • Kayaks • Sunsets

The Havana Cabana is your home away from home. Take time to breathe and just be by soaking in your surroundings and being with the people that matter most. We strive to provide you with a relaxing atmosphere and great amenities. You will have full access to your own private, sandy beach (directly behind the home) with amazing sunset views and great fishing. We provide 3 adult kayaks, one double and one child (under 150 pounds), and a pedal boat. Great outdoor fire-pit for s’mores and memories.

Last-Minute Deal! River View/ Firepit/Kayaks/Bikes

Escape to this charming, eclectic cabin bungalow on the tranquil Rock River, perfect for couples, families, and friends. Just steps from the water, it offers stunning views, abundant wildlife, and a peaceful ambiance while remaining close to shops and restaurants. Inside, enjoy vibrant decor, cozy living spaces, and natural light throughout. The large wrap-around deck invites relaxation, with steps leading directly to the river. A serene, thoughtfully crafted retreat for your perfect getaway

Octagon treehouse Hottub-pool-fireplace-firepit

Unique "tree house" - an octagon tiny house, surrounded by the woods! 2 bedroom, 2 bathroom home you can enjoy the views of nature all around, with floor to ceiling windows. One king bed, one queen bed. Modern comforts with fun flash blacks. Private hot tub and firepit look into serene woods! Sit by the indoor gas fireplace and enjoy our record collection. Soak in a Japanese soaking tub. Enjoy fall colors or watch snow fall! Community indoor poor, seasonal outdoor pool, gym access

Custom Floating Suite-HOT TUB!

Enjoy a stay directly on the backwaters of the Mississippi River. This custom cabin is floating right on the water, and you won't find anything like it! Grab your loved one or friend and surround yourself in nature, while soaking in the hot tub on the floating patio, or in the beautiful tub inside. Relax in the king size bed thats in front of one of the two fireplaces. The cabin has everything you need, including a small kitchen. This floating oasis is located at Millennium Marina.

Eden Farm: Family Stays & Intimate Moments

Unwind and find your inspiration just 1.5 hours from Chicago at our Elite Farm Retreat. Designed for executives, families, and intimate weddings. High-speed Wi-Fi, Smart TVs, and workspaces enhance your stay. This 5,000 sq ft estate blends modern comfort with rustic charm on 10 peaceful acres near Lake Geneva. Luxurious bedrooms, a Jacuzzi, and premium entertainment await. Two outdoor cameras monitor the front yard and driveway. No indoor cameras. Book now.

LilyPad-pondside cabin, kayaks, trail, country

Perfect for a couple, an outdoorsman, or travelers! This country cabin is located on our 20 acre property, less than 10 minutes from Rend Lake, I 57 access, and public hunting land and within an hour of the Shawnee National Forest. Includes the use of kayaks, hammocks and a walking trail. Portable bow target use available upon request. Gas grill, firepit and firewood available. Outdoor outlet and spigot. Children welcome!

Hidden Gem - Rock River

The Eagle’s Nest: A Cozy Family Escape! Unplug and unwind at The Eagle’s Nest, a renovated cabin on stilts nestled on 5 private wooded acres with stunning views of the Rock River and Kyte Creek—just 5 minutes from Oregon, IL! Hike, fish, kayak, or relax by the firepit under the stars. Perfect for families and outdoor lovers, this peaceful retreat offers adventure and tranquility. Book now and escape the city hustle!

Virginia Lake Getaway/Fishing/Hot Tub/Hammock

Welcome to your charming log cabin located in Virginia, IL. This 1-bedroom, 1-bathroom cabin is designed to provide you with rustic comfort, making your stay truly exceptional. Nestled on a bluff overlooking the serene Virginia Lake, this 1850's log cabin combines historic charm with modern luxuries. Set on 80acres of timber and water for you to explore. Hike, kayak, fish or just relax and enjoy!