
Vacation rentals with a kayak in Winchester
Find and book unique kayak rentals on Airbnb
Quick stats about vacation rentals with a kayak in Winchester

Total vacation rentals
Explore 20 vacation rentals in Winchester

Nightly prices starting at
Winchester vacation rentals start at G$2,092 GYD per night before taxes and fees

Verified guest reviews
Over 800 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Winchester vacation 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 kayak rentals in Winchester
Guests agree: these kayak rentals 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.

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!

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 :)

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

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.

Serene Retreat with High-Speed WiFi
This Riverside Retreat at River Walk is the perfect getaway for those seeking river life with high-speed WiFi and modern amenities. Built in the 1800s, this historic cabin offers unique charm. Enjoy a serene waterfall on the property, private access to the Elk River, and sensational views from your porch. We also provide complimentary gourmet coffee to enhance your stay. River Walk is ideal for a staycation or a truly memorable experience!

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.

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
House rentals with a kayak

Cozy Two Bedroom Cabin with Hot Tub in Waters Edge

Kayak Kove* DOCK* Lakefront*NEW

Barefoot Dreams

Lakefront Lodge

Lakeside Serenity: Cove Retreat

Blue Heron Lake House

Peaceful Getaway on Kayak Way – Winchester

Tennessee Pearl: lakefront-amazing views-lake toys
Cottage rentals with a kayak

The Someday Lake House at Tims Ford Lake

Bluebird Rest- Peaceful Lake Retreat

Chattanooga River Escape

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

Dock & Hot Tub: Tennessee River Cabin Getaway

The Cabin

Lillypad Cove at The Retreat at Water's Edge

Eagle Lake Cabin Coalmont

Cabin at Normandy Lake

Sunflower Shores Log Cabin Dunlap Tn Deerhead Lake

Tennessee River Gorge® Treehouse 2
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$49,158 GYD | G$43,301 GYD | G$49,158 GYD | G$49,158 GYD | G$69,031 GYD | G$71,960 GYD | G$71,123 GYD | G$74,679 GYD | G$55,643 GYD | G$54,179 GYD | G$66,102 GYD | G$54,597 GYD |
| 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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- Rentals with pools Winchester
- Rentals with outdoor seating Winchester
- Rentals with lake access Winchester
- Rentals with a patio Winchester
- Rentals with a fireplace Winchester
- Family-friendly rentals Winchester
- Rentals with a washer and dryer Winchester
- Rentals with a fire pit Winchester
- Cabin rentals Winchester
- House rentals Winchester
- Pet-friendly rentals 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
- Rock City
- Hunter Museum of American Art
- Creative Discovery Museum
- South Cumberland State Park
- Raccoon Mountain Caverns & Campground
- Chattanooga Zoo
- U.S. Space & Rocket Center
- Cathedral Caverns State Park
- Dublin Park
- Point Park
- Cumberland Caverns
- Burritt on the Mountain
- Chattanooga Whiskey Experimental Distillery
- Old Stone Fort State Archaeological Park
- Huntsville Botanical Garden
- Finley Stadium
- Lowe Mill Arts And Entertainment
- Short Mountain Distillery
- Discovery Center




