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, 206 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, 295 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".

Guest favourite
Cabin in Tracy City
4.92 out of 5 average rating, 434 reviews

Waterfall Log Cabin

Cozy Log Cabin just feet away from the top of our 2 magnificent private waterfalls. The Falls at Sewanee Creek is located in America’s most biodiverse area on Tennessee's Eco-Rich Cumberland Plateau. Walk to the observation bench at the top of the biggest 50 ft waterfall. Follow the trail behind the falls. Adventure awaits on a rugged, bouldering hike, past cascades and the second big waterfall to two private caves. Disclaimer: Flow of all Waterfalls is subject to weather fluctuations.

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
4.93 out of 5 average rating, 192 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.

Top Guest favourite
Home in Tracy City
4.98 out of 5 average rating, 116 reviews

Little Green Cottage

Relax & unwind where mother nature meets modern nature at the Little Green Cottage. Each space is thoughtfully designed for a comfortable & luxurious stay. Enjoy an open layout w/ vaulted ceilings & natural earth-tone features, a full functioning kitchen & dining area, bedrooms w/ king size beds that each come with their own attached bathroom & a large screen porch w/ a view that will take your breath away. All the fun, recreational activities are right outside your door! Dog friendly!

Top Guest favourite
A wooden dock extends over the tranquil water, featuring kayaks and paddleboards secured alongside. An upper deck with several chairs offers a relaxing space, while views of the lush surroundings create a calming atmosphere. The water sparkles under clear blue skies.
Home in Winchester
4.98 out of 5 average rating, 117 reviews

Lake Home, Dock, Theatre, Hot Tub, FirePit, Kayaks

Take it easy at this unique and tranquil getaway. This beautiful lake home is one of it's kind at Tim's Ford. The house is nestled in a quiet rural neighborhood with woods in the backyard. The dock is only a small golf cart ride away. Enjoy beautiful lake views at your own private dock! This house is equipped with an amazing home theatre system, game room, hot tub, fire pit, kayaks and plenty more amenities! Tim's Ford Dam is only one mile away and has a public boat launch for you :)

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
4.98 out of 5 average rating, 128 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.

Top 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
4.99 out of 5 average rating, 229 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 charming cabin sits amid lush green grass, complemented by surrounding trees and shrubs. An American flag gently waves from the front porch, which features welcoming seating. Sunlight bathes the exterior, highlighting the rustic logs and metal roof.
Cabin in Fayetteville
4.84 out of 5 average rating, 165 reviews

Cozy Cabin with River Access

Rustic bliss at this 3BR/2BA log house on the Elk River—only 5 min from downtown & 15 min from Jack Daniel's Distillery! Modern perks for ultimate comfort: high-speed WiFi, 50" HDTV w/ streaming, stocked kitchen, washer/dryer, AC, heat, grill, crackling fire pit w/ firewood, hammock by the waterfall, kayaks, and complimentary gourmet coffee. Pet-friendly paradise! Sleeps 8: 1king, 2queens, sofa. Effortless self check-in; free parking. Your serene riverfront adventure awaits!

Guest favourite
Cabin in Coalmont
4.98 out of 5 average rating, 369 reviews

The Coalmont Cabin - Romantic Lakefront Escape

A quiet lakeside retreat made for slow mornings and star-filled nights. Wake to coffee on the deck as the fog drifts across the water, geese gather along the shoreline, and the world feels still for just a little longer. Spend your afternoons out on the lake, gliding through lily pads in a moment that feels like a scene from The Notebook. Tucked among the trees with a saltwater spa beneath the stars, The Cabin is where peaceful seclusion meets unforgettable memories.

Guest favourite
A serene lake scene features a boat silhouetted against a vibrant sunset, where rays of light filter through scattered clouds. The calm waters reflect the warm hues of the fading day, with distant tree-covered hills framing the horizon.
Cabin in Manchester
4.89 out of 5 average rating, 246 reviews

Fire Lake Lodge Volleyball, Hot Tub, Kayaks!

PRIVACY, FUN, and HI SPEED INTERNET await for all at the newly finished Fire Lake Lodge at beautiful Normandy lake. You can Walk to the beach/lake access area from the cabin, but why walk when you have your very own golf cart and kayaks! Hot tub, Beach Volleyball court, pool table, 6’ fire pit, outdoor shower and more! Everything is PRIVATE, nothing is shared on this almost two acre property located right above the boat ramp at fire lake.

Top Guest favourite
A spacious screened porch features comfortable seating, including a cozy sofa and armchair, overlooking a serene lake view. Large glass panels invite natural light, while a wooden deck extends outside, providing access to the lakefront and enhanced outdoor experience.
Home in Tracy City
5 out of 5 average rating, 105 reviews

Catch & Release - Spacious Lakefront Getaway

Escape to this bright, spacious 2BR/2BA lakefront retreat—one of the largest homes in the Retreat at Water’s Edge. Sip coffee on the screened porch, kayak or fish from the semi-private dock, and gather by the firepit at sunset. Minutes from world-class hiking, including the nationally acclaimed Fiery Gizzard Trail, yet set on a calm, family-friendly lake perfect for kids to explore and unplug. Ideal for couples, families, or both.

Popular amenities for Winchester kayak rentals

When is the best time to visit Winchester?

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Avg. price$454 NZD$444 NZD$454 NZD$403 NZD$566 NZD$590 NZD$583 NZD$612 NZD$456 NZD$444 NZD$542 NZD$448 NZD
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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 $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 800 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, Wifi and Pool across Winchester rentals

  • 4.9 Average rating

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

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