Holiday rentals with a kayak in Winchester

Find and book unique kayak rentals on Airbnb

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 830 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!

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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Guest favourite
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
4.86 out of 5 average rating, 211 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".

Top Guest favourite
A firepit area is surrounded by Adirondack chairs, arranged in a circular formation on a flat surface near the calm waters of the lake. Lush greenery and trees frame the peaceful setting, with the serene water reflecting the surrounding nature.
Home in Tracy City
5 out of 5 average rating, 101 reviews

Lakefront w/ Hot Tub + Kayaks + Firepit

Sycamore Shores is a private, lakefront (75 acre calm water lake), home located near Monteagle and Sewanee. It's nestled among the trees with an oversized, covered deck to take in the amazing views of the lake. Whether you’re coming to take the kayaks out or fish on the lake, hike to nearby waterfalls, enjoy a hot tub under the stars, zip line, or to enjoy a concert at the Caverns (ONLY 15 MINS AWAY!), Sycamore Shores is the perfect getaway! Stay one night or a week, you'll love your time here!

Guest favourite
Cabin in Tracy City
4.92 out of 5 average rating, 443 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
4.92 out of 5 average rating, 199 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, 124 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!

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
4.96 out of 5 average rating, 147 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
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, 238 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

Top Guest favourite
Cabin in Coalmont
4.98 out of 5 average rating, 381 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
4.88 out of 5 average rating, 251 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, 115 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.

Top Guest favourite
A spacious outdoor deck features a wooden dining table and chairs, overlooking a serene lake. The calm water reflects the colors of the sunset, surrounded by trees. A stone fire pit is visible, enhancing the tranquil setting.
Home in Winchester
4.98 out of 5 average rating, 109 reviews

Best Views on Lake, TIki Hut, Boat Rental + More

If you are looking for the perfect getaway to a luxury lake home that has countless amenities and postcard like views then look no further! This newly renovated lake front home boasts the best views on the lake, tiki hut, multiple outdoor decks, covered patio, hot tub, game room, theatre, kayaks, SUPs and plenty more! This is truly a one of kind property. We look forward to serving you!

Popular amenities for Winchester kayak rentals

When is the best time to visit Winchester?

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Avg. price$452 NZD$441 NZD$452 NZD$462 NZD$535 NZD$620 NZD$580 NZD$609 NZD$453 NZD$441 NZD$539 NZD$445 NZD
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