Vacation rentals with a kayak in Illinois

Crooked Lake Getaway- lakefront

Newly built, secluded 2 bedroom, 2 bath lakehouse on multiple wooded acres nestled between Kennekuk County Park & Kickapoo State Park. Sleeps six (2 bedrooms with 2 queen beds plus pull-out couch). Access Kickapoo mountain bike trails from the property. Spend your time in complete privacy, swimming or paddling kayaks & canoes down the mile-long Crooked Lake, playing on the private dock and dockside Lillypad (floating water mat), relaxing in the hottub, or making s’mores around the firepit.

Private Guest Lake House On 37 Acres In Country

Private guest lake house, located next to main house, on private lake in the country. 2 bedroom, 1 full bath, full kitchen, washer and dryer and large attached screen porch. Private 37 acres of woods and prairie. Fishing and walking trails. Great window views of lake, woods, prairies and river valley. Please note, this guest house is located 1 mile down a county maintained gravel road. 25 minutes from Galesburg, IL, 20 minutes from Monmouth, IL and 35 minutes from Macomb, IL.

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

Shagbark Landing

Forget your worries in this spacious and serene space. Drive down the lane to a secluded 3 bedroom home newly furnished. Enjoy yourself in an open concept floor plan where there is lots of room to spread out. Spend your evenings in the living room or the family room that has a fireplace. From the family room you can step out on a deck and enjoy the view of the pond. We are located 8.5 miles from Vandalia where there are historical landmarks, great restaurants, and quaint shops.

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.

TheGlassCabin@HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

Cozy Lakefront Retreat w/ Dock, Kayaks & Games

Welcome to Lake Shore Cottage, hosted by Beyond the Path Vacation Rentals, where your experience is our priority. Enjoy lakefront living: fish from the private dock, paddle kayaks, relax by the fire pit, and enjoy the peaceful waterfront views. Comfortable beds, fast Wi‑Fi, huge digital game board, smart TV, fully equipped kitchen, quiet safe neighborhood, minutes to Scovill Zoo, Devon Amphitheater, Nelson Park, Splash Cove, restaurants, shopping, and available boat rental.

Hidden Gem - Rock River

The Eagle’s Nest: A Cozy Family Escape! 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. Book now and escape the city hustle! For price transparency, the nightly rate includes a 15.5% Airbnb service fee and a flat $80 cleaning charge to cover the cleaning service bill.

Eden Farm: Family Stays & Intimate Moments

Unwind and find your inspiration just 1.5 hours from Chicago at the Ten Acre Farmhouse Retreat. Designed for families, intimate moments, and retreats. 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.

Lake House off Route 66

Lake House Cabin is the best property in the area and offers a 2 acre lot at the end of a peninsula off Route 66. *Includes private lake access with fishing dock. *House has a fenced in dog area with doggie door. *Swimming, paddle boat and fishing allowed* *Crappie, bass bluegill, blue cat and channel cat. *Smoking allowed outside* *Pets 2 max *Crate pets when left alone. *4 person paddle boat *4 Guests Max including kids. *Wifi *No parties*

Private Cabin w/Pool on Lake Centralia, sleeps 12.

Welcome to Deer Creek Cabin on Lake Centralia. Relax with the whole family at this peaceful private retreat. A large deck surrounds the pool for all your family fun. Fishing and kayaking are just steps away. Enjoy your morning coffee in the screened-in porch overlooking a quiet cove of the beautiful lake. It is common to see deer, geese, ducks, turtles, and blue heron. As night falls, cozy up around the fire pit to make more family memories.

Riverfront Retreat | Kayaks • Fire Pit • Bikes

Wake up directly on the Rock River and unwind at this cozy 2-bedroom waterfront cottage. Perfect for couples, small families, girls’ weekends, and Quad Cities getaways. 🌊 Riverfront views 🛶 Kayaks + canoe 🔥 Riverside fire pit 🚲 2 bikes + nearby trail 🕹️ Pac-Man arcade 🎶 Record player ☕ Coffee + tea bar 🔥 Gas fireplace 🐴 Horse views 📺 55” TV 🛏️ 2 queen bedrooms Relax, recharge, and enjoy life on the river.