
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.

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)

*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".

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!

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.

Tiny Home in the Mountains w/firepit and Hot Tub
Allow yourself to take a deep breath in and relax at the Bird House. Our home is well-designed with extra space for a family yet still small enough to feel cozy. Relax in the private hot tub or around the firepit with adirondack chairs, café lights, and firewood provided!! Grill out on gas grill. Beautiful landscaping and plenty of privacy. Enjoy the peacefulness and return to a simple pace of life here at the Bird House. 3 bicycles are provided in addition to a nice canoe for use on lake!

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.

Lakeside Family Escape-Modern Log Home; Pvt. Dock
Escape to our secluded lakeside retreat, overlooking a tranquil cove and featuring peaceful water views, modern accommodations and appliances, stylish interiors, a game room and plenty of room for making family memories. Enjoy breathtaking lake views from our 2 spacious decks, swim or fish off our private dock, or explore the stunning cove views on a kayak. Rent a boat or jet ski nearby, play a round of golf or visit the world-famous Jack Daniel's Distillery and the Lynchburg town square.

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!

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 :)

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

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.

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.
Popular amenities for Winchester kayak rentals
Holiday House Rentals with a Kayak

Cozy Two Bedroom Cabin with Hot Tub in Waters Edge

Lake Life

Whitetail Creek Lodge Close to Campus

Barefoot Dreams

Spring Fun, Fishing, & Fire Pit. Cove Sweet Cove!

Aqua-dream

Lakeshore Modern- steps to water

A-Frame on Tims Ford Lake Private Boat Dock w/slip
Cottages with a kayak

Tims Ford Lake Cottage Twin Creeks Resort & Dock!

Cozy Tiny Cottage Escape, Tennessee

Magical Tiny Cottage Escape, TN

Canoe Cove - Charming Lakefront Retreat, Sleeps 6

Waterfront Cottage at Ketners Mill Arena-2

Clementine Cottage

Stunning Cottage Nestled Amidst Trees with Fire

Tim's Ford Lake 4 bedroom cottage with golf cart
Cabin rentals with a kayak

The Cabin

Lillypad Cove at The Retreat at Water's Edge

Scenic Cabin Escape, Monteagle TN

Cabin Escape w/ Fire Pit, Monteagle

Atypical Cabin in Clifftops near Sewanee

Cabin at Normandy Lake

Vinay's Valley Adventure at The Retreat

Seq River 2BR Cabin - newly remodeled. Tiny home 1
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $450 NZD | $440 NZD | $450 NZD | $460 NZD | $533 NZD | $618 NZD | $578 NZD | $606 NZD | $452 NZD | $440 NZD | $537 NZD | $443 NZD |
| Avg. temp | 5°C | 8°C | 12°C | 17°C | 21°C | 25°C | 27°C | 27°C | 23°C | 17°C | 11°C | 7°C |
Destinations to explore
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- Cloudland Canyon State Park
- Tennessee Aquarium
- Monte Sano State Park
- Rock City
- Chattanooga Choo Choo
- South Cumberland State Park
- Coolidge Park
- Point Park
- Hunter Museum of American Art
- Von Braun Center, North Hall
- Chattanooga Zoo
- Raccoon Mountain Caverns & Campground
- Old Stone Fort State Archaeological Park
- Creative Discovery Museum
- U.S. Space & Rocket Center
- Huntsville Botanical Garden
- Cathedral Caverns State Park
- Cumberland Caverns
- Lowe Mill Arts And Entertainment
- Burritt on the Mountain
- Short Mountain Distillery
- Discovery Center
- Chattanooga Whiskey Experimental Distillery
- Henry Horton State Park





