Holiday rentals with a kayak in Illinois

Lakeside Lodge w/Private Beach and Dock

Nestled on the shores of Borah Lake, our 2-story lodge is the perfect escape for families and anglers. Enjoy a myriad of water adventures: swim, fish, or dock your boat right at your doorstep, or regular viewing of White Squirrels and other wildlife💗 As the sun sets, retreat into our cozy haven or gather around a crackling campfire. Embrace the essence of lake-life in a place where each moment is not just spent, but cherished. Ready for an unforgettable stay? Book your dream retreat today! 😍

Location · Outdoor spaces · Hospitality

GOOSE ISLAND CABIN -Secluded Riverside Eco-Retreat

Nestled along the banks of the Rock River under tall oaks, ye ol cabin was built by early settlers in 1907. Legit rustic charm. Secluded yet only 10 mins from the fun town of Oregon. 100 acres of private property, bordering Lowden-Miller State Forest. Includes use of canoes/kayaks, large riverfront yard, grills, hammocks, deck, porch and firewood. $33/night per person or pet after first 2 people. Message Tim about accomodating larger groups and events. Closed for winter November through March.

Location · Value · Air conditioning

Riverfront Firepit, Kayaks, Huge Deck

Firepit ready for relaxing nights by the river. Kayaks included for warm days Wake up to sweeping Rock River views, sip coffee on the wrap-around deck, paddle out in the kayaks, and end your evening by the firepit as the sky glows at sunset. This eclectic riverfront bungalow blends vibrant décor with cozy comfort and seamless indoor-outdoor living. Perfect for girls’ weekends, fishing trips, romantic escapes, or peaceful fall getaways — just steps from the water and minutes to shops and dining

Location · Value · Quiet

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.

Outdoor spaces · Value · Cleanliness

LilyPad-pondside cabin, kayaks, trail, country

Great for a couple, an outdoorsman, or travelers! This cabin is located on our 20 acre property, less than 10 minutes from Rend Lake, I57 access, and public hunting land and within 1 hour of the Shawnee National Forest. Includes use of kayaks, fishing poles for the catch & release pond, and a walking trail. Bow target use available upon request. Gas grill, firepit and firewood. PLEASE NOTE: its a 12x20 studio cabin with 1 full bed and 1 twin sized foam couch sleeper. We don't allow pets.

Location · Outdoor spaces · Amenities

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

Value · Location · Decor

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.

Value · Location · Amenities

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 !

Outdoor spaces · Value · Pets

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.

Value · Location · Kitchen

Platypus Hills, Lake, Heated Pool, Hot tub,Firepit

This cozy 2-bedroom country house sits on 8 acres, sleeps 4 and overlooks Clinton Lake with amazing views. We offer a hot tub, heated pool, kayaks, 10 miles of hiking, hunting, and horse trails. The boat ramp is located at the end of the driveway and across the street. We are located 30 minutes between Bloomington & Champaign. All guests must be 18+. An additional $50 per person per night over 2. Pool open May-Sept. PLEASE READ THE ENTIRE LISTING TO ENSURE IT MEETS YOUR NEEDS.

Outdoor spaces · Value · TV

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!

Value · Outdoor spaces · Kitchen

Scenic 2BR A-Frame w/ Hot Tub & Views

Stay at Wildflower Cabin, a scenic 2BR A-frame perched atop Sunrise Hill with the best views of the three cabins. This pet-friendly retreat features a wildflower-inspired interior, hot tub, stocked pond, Smart TV, WiFi, workspace & furnished kitchen. Enjoy the patio, firepit & nearby wineries, Giant City & hiking. Perfect for couples or small groups looking for beauty, comfort & nature in Southern Illinois.

Outdoor spaces · Value · Wi-Fi