
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 $13 SGD 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 & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Winchester holiday rentals include wifi 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 rentals with kayak in Winchester
Guests agree: these rentals with 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".

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.

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! We even have a 2022 Crest tritoon with a 200 HP motor that is available to rent for experienced boaters! This is truly a one of kind property. We look forward to serving you!

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.

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!

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.

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

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!

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.

Blue Heron Lake House
The Blue Heron Lake House is situated in the Tennessee River Gorge and takes advantage of the breathtaking lake and mountain views from almost every room in the home. Come and enjoy the great outdoor living space with multiple decks. Fish and swim off of long covered dock or lounge in the sun. With kayaks, canoes and a paddleboard for you the explore the beautiful Tennessee river. Dock has a lift for a pontoon. Svec Connect Internet Provider 1 Gig.

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 kayak rentals in Winchester
House rentals with a kayak

Cozy Two Bedroom Cabin with Hot Tub in Waters Edge

Kayak Kove* DOCK* Lakefront*NEW

Whitetail Creek Lodge Close to Campus

Barefoot Dreams

A-Frame on Tims Ford Lake Private Boat Dock w/slip

Lakefront Lodge

Lakeside Serenity: Cove Retreat

Peaceful Getaway on Kayak Way – Winchester
Cottage rentals with a kayak

Bluebird Rest- Peaceful Lake Retreat

Lakeside Cottage Inside Full-Service Marina Resort

Canoe Cove - Charming Lakeside Retreat, Sleeps 6

Waterfront Cottage at Ketners Mill Arena-2

Clementine Cottage

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

Mountain lake log cabin at Deerhead Lake

The Cabin

Charming Tiny Cabin Minutes from Town

Atypical Cabin in Clifftops near Sewanee

Cabin at Normandy Lake

Sunflower Shores Log Cabin Dunlap Tn Deerhead Lake

Tennessee River Gorge® Treehouse 2

Hickory Hideaway at The Retreat at Deer Lick Falls
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $338 SGD | $331 SGD | $338 SGD | $300 SGD | $421 SGD | $439 SGD | $434 SGD | $456 SGD | $340 SGD | $331 SGD | $404 SGD | $333 SGD |
| 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 |
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- Pet-friendly rentals Winchester
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- Rentals with a patio Winchester
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- Family-friendly rentals Winchester
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- Rentals with a firepit Winchester
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- Rentals with lake access Winchester
- Rentals with a kayak Franklin County
- Rentals with a kayak Tennessee
- Rentals with a kayak United States
- Cloudland Canyon State Park
- Tennessee Aquarium
- Monte Sano State Park
- Chattanooga Choo Choo
- Coolidge Park
- Hunter Museum of American Art
- Point Park
- South Cumberland State Park
- Creative Discovery Museum
- Raccoon Mountain Caverns & Campground
- Chattanooga Zoo
- Old Stone Fort State Archaeological Park
- U.S. Space & Rocket Center
- Von Braun Center, North Hall
- Short Mountain Distillery
- Cathedral Caverns State Park
- Cumberland Caverns
- Huntsville Botanical Garden
- Lowe Mill Arts And Entertainment
- Burritt on the Mountain
- Discovery Center
- Chattanooga Whiskey Experimental Distillery
- Chattanooga Convention Center
- Tennessee River Park





