Holiday rentals with a kayak in Winchester

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Top-rated Accommodation with a Kayak in Winchester

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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A comfortable living area is observed, featuring a light-colored sectional sofa and a dark wooden coffee table. Large windows provide natural light, while a rustic dining table and chairs are visible in the background. Decorative wall art and assorted accents highlight the cozy atmosphere.
Cabin in Winchester
4.85 out of 5 average rating, 199 reviews

Private Dock - Best Cabin Tims Ford Lake

Great cabin located directly on Tims Ford Lake. Cabin has been updated and includes nice, well stocked kitchen as well as a deck (with grill). Enjoy our dock - fish, swim and use our two kayaks, paddle board and a canoe. Plenty of space to tie your boat up to our dock in a mostly private cove. Please read the guest access section for more details on lake access. Close to some great attractions - Jack Daniels Distillery (19 mi), Bonnaroo (25 mi), Univ. of the South (19 mi), Winchester (5 mi)

Guest favourite
An outdoor fire pit area is illuminated by string lights, creating a cozy atmosphere at night. Four wooden chairs are positioned around a central fire pit, surrounded by landscaping stones and plants. The tiny home stands in the background, showcasing large windows.
Tiny home in Tracy City
4.93 out of 5 average rating, 291 reviews

*The Honeysuckle House* - Tiny House, Big Living!

The Honeysuckle House is a luxury waterfront tiny home created for reconnection, rejuvenation and restoration. It is a respite where you can come and be one with nature as you look out upon the peaceful lake from the oversized screened-in porch, the open air deck or from the private fire pit area. This home sits on 1 acre with large, mature trees and has direct access to the lake for paddle boarding, fishing, kayaking or canoeing. The Honeysuckle House is the perfect place to come and "unplug".

Top Guest favourite
A well-lit living area features large windows allowing natural light to flood the space. A comfortable brown sofa is complemented by patterned cushions. Glass doors open to a deck, and a small table with decorative items sits nearby.
Tiny home in Tracy City
4.98 out of 5 average rating, 148 reviews

Cozy Tiny Home w/large deck, hot tub and firepit

The Trail House is perfectly placed among the trees with many tall windows to take advantage of the gorgeous views. The large 2-tiered deck has two separate sitting areas. You can take the kayaks out for a day on the lake. Hike, bike, cave, kayak, fish, and swim at the base of the waterfalls or sit and relax. Do it all, do absolutely nothing, or a little of both here at the Trail House. Have a second home on same property you can rent listed as New Tiny Home in the Mountains. Last Picture.

Guest favourite
The living area features warm wooden walls and a vaulted ceiling complemented by large windows that offer natural light. A comfortable sofa is arranged in front of a stone fireplace, with a wooden coffee table placed centrally, enhancing the cozy ambiance.
Cabin in Dunlap
4.96 out of 5 average rating, 146 reviews

Sunflower Shores Log Cabin Dunlap Tn Deerhead Lake

Sunflower shores is a true log cabin, in a small neighborhood built on the shores of a clean quiet lake in Middle Tennessee. Relax, unwind, have coffee or cocktails on the deck. Swim, fish, take out the canoe or kayak, birdwatch, hike in nearby Savage Gulf or Fall Creek Falls. Go to Chattanooga, take in the sights and come back for an evening by the outdoor fire ring, or inside fireplace. Pick apples at the local orchard or buy Amish goods from the local farms. Unplug and enjoy your life.

Guest favourite
A two-story cottage is elevated on wooden stilts, surrounded by trees and fallen leaves. Large windows provide views of the natural surroundings, while a spacious deck wraps around the structure, offering outdoor seating options.
Cottage in Whitwell
4.92 out of 5 average rating, 169 reviews

Relaxing 1 bedroom cottage at Ketners Mill Arena

1 bedroom relaxing cottage with a pullout sofa for additional guests. This cottage has a full kitchen - 1 bath and a very nice deck where you can hear the sounds of Ketners Mill dam. This property is a great get away but also not to far away from Chattanooga and and has an enormous amount of outdoor activity near by. This cabin sits directly on the Sequatchie River. Fish from your very on secluded beach, kayak down the sequatchie river or take a walk on the farm and pet some of our horses.

Guest favourite
A cozy bedroom area features a wooden ladder leading to a loft space. A bed with a plaid duvet cover is positioned against a wall of natural wood paneling, while a rustic door opens to a bathroom with modern amenities.
Cabin in Fayetteville
4.86 out of 5 average rating, 173 reviews

Nature’s Tiny Riverside Hideaway

Nature's Riverside Hideaway is a tiny cabin and the perfect get-a-way for those who want a natural river experience but want HIGH SPEED WiFi and modern amenities. Only 2 miles from the historic Fayetteville square and approximately 15 minutes from Jack Daniels Distillery in Lynchburg, Tennessee, a waterfall located on the property, private access to the Elk River and a separate entrance, River Walk is perfect for a close to home staycation or a unique experience that you will never forget!

Guest favourite
A modern cabin is shown with a sleek design, featuring a covered porch with a rail and stone base. Large windows allow natural light to enter, surrounded by trees in autumn colors. A grassy area is visible in the foreground.
Home in Tracy City
4.97 out of 5 average rating, 116 reviews

Cozy Two Bedroom Cabin with Hot Tub in Waters Edge

New 2 bedroom cabin in the Water's Edge community. Spacious family room to enjoy fireplace, TV, and dining area. Private hot tub! Master bedroom has a king sized bed. The second bedroom has 2 twin bunk beds, trundle, and a loft. Outdoor living space patio with a grill, table, couch, and firepit. Multi video game system. There is a community lake, playground, and hiking trail. We have two stand-up paddle boards, 1 adult kayak, and 1 child kayak. Pack n' play and high chair available.

Guest favourite
The image captures the Tennessee River surrounded by rolling green hills, illuminated by soft sunlight breaking through the clouds. Lush vegetation is visible along the riverbank, creating a serene coastal landscape contrasted by the dramatic sky.
Apartment in Chattanooga
4.93 out of 5 average rating, 202 reviews

River Gorge Condo 10 min from Downtown and trails!

This unit is part of the newly constructed River Gorge Condos. The condos are right on the Tennessee River. You will get to enjoy the views of the Tennessee River Gorge and the surrounding mountains! This is a perfect spot for a relaxing weekend getaway! Our location is just minutes from great trails and other activities if you love the outdoors. We are also only 10 minutes from Downtown Chattanooga. There are many great restaurants, the TN aquarium, and other tourists attractions.

Top Guest favourite
A welcoming entryway is presented with red double doors flanked by seasonal decorations. A wooden porch features a patterned rug and a simple chair beside a seasonal wreath. Natural elements like leaves and potted plants add to the cozy atmosphere.
Guesthouse in Tracy City
4.99 out of 5 average rating, 120 reviews

Fiery Gizzard Homeplace & Cottage

A private cottage located close to area restaurants and outdoor activities. Approximately 5 minutes to FIERY GIZZARD trailhead as well as dining in Monteagle and Tracy City. Our cottage has a private courtyard where you can grill, chill, and make a fire! A large custom walk-in shower with great water pressure and endless hot water. A large smart tv with excellent internet. Very comfortable bedding and a nice leather recliner. Snacks and drinks in the refrigerator are complementary.

Guest favourite
A charming black cottage nestled among tall trees is visible. The entrance features a small deck with steps leading to the door. A kayak rests on the ground nearby, and seating areas can be seen on the gravel pathway, surrounded by lush greenery.
Tiny home in Tracy City
4.98 out of 5 average rating, 198 reviews

2BR Nature Getaway in Tiny Home w/ Lake access

Nature's Nook is a charming two-bedroom cottage. Combining nature with cutting-edge design draws inspiration from all over. Providing a fairytale experience with a cozy interior amidst towering trees. Nature's Nook embraces the beauty of nature with the inside scent of a campfire-lit night to birds singing good morning. This provides the ideal getaway to relax but still includes hiking and adventure. Nature is calling you at the Nook. . . Follow us on our socials @NaturesNookTN

Guest favourite
A serene cabin is surrounded by colorful autumn foliage, reflecting beautifully on the calm water. The warm glow from large front windows invites guests to experience the cozy atmosphere inside, while a small dock is visible along the shoreline.
Cabin in Coalmont
4.98 out of 5 average rating, 324 reviews

The Coalmont Cabin – Romantic Lakefront Escape

The Coalmont is a 4 acre waterfront retreat on top of the South Cumberland Mountains of Tennessee, between Nashville and Chattanooga. This 460 sq ft "tiny" cabin sleeps up to 4. Amenities abound with boats, hot tub, fishing, zip line, lawn games, large decks for gathering, fire pit, and beautiful scenery. Perfect retreat for couples looking for a romantic getaway, families wanting to unplug and reconnect with quality time, or anyone looking for a quiet place to work remotely.

Top Guest favourite
The interior showcases high ceilings with a large clock prominently displayed above a comfortable seating area. Natural light filters through multiple windows, highlighting a cozy living space that opens onto a covered deck featuring a circular seating arrangement around a firepit.
Tiny home in Tracy City
4.99 out of 5 average rating, 289 reviews

Cozy tiny home ☆Sleeps 4 w/ great outdoor space

Relax & unwind at our tiny home located in Tracy City Sleeps 4-Queen bed in private bedroom & upstairs loft Covered deck w/ gas firepit Campfire in backyard Electric fireplace inside Outdoor obstacle course for kids Fully stocked kitchen 3 Tv's, DVD players & DVD's Fishing poles Great restaurants and shops Bike and hiking trails nearby Kayak & canoe rentals Gas grill 90 min from Nashville, 45 min from Chattanooga, & 15 min from the University of the South in Sewanee.

Popular amenities for Winchester kayak rentals

Quick stats about holiday rentals with a kayak in Winchester

  • Total holiday rentals

    Explore 20 holiday rentals in Winchester

  • Nightly prices starting at

    Winchester holiday rentals start at $139 AUD per night before taxes and fees

  • Verified guest reviews

    Over 720 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Winchester holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Winchester rentals

  • 4.9 Average rating

    Winchester stays are highly rated by guests—averaging 4.9 out of 5!