
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)
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*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".
LocationValueIndoor spaces

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!
ValueLocationWalkability

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.
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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.
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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!
Outdoor spacesLocationParks

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.
LocationOutdoor spacesAccuracy

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 :)
Outdoor spacesLocationAccuracy

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
ValueOutdoor spacesLayout

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.
LocationValueBathroom

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

Lake Life
LocationOutdoor spacesCleanliness

Whitetail Creek Lodge Close to Campus
Outdoor spacesLocationPets

Barefoot Dreams
Outdoor spacesValueLaundry

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

Aqua-dream
LocationOutdoor spacesSleep quality

Lakeshore Modern- steps to water
LocationOutdoor spacesIndoor spaces

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

Lakefront Lodge
LocationOutdoor spacesKitchen
Cottages with a kayak

Tims Ford Lake Cottage Twin Creeks Resort & Dock!
Location

Magical Tiny Cottage Escape, TN

Clementine Cottage
LocationOutdoor spacesCleanliness

Stunning Cottage Nestled Amidst Trees with Fire

Relaxing 1 bedroom cottage at Ketners Mill Arena
LocationValueAmenities

Cozy Tiny Cottage Escape, Tennessee

Canoe Cove - Charming Lakefront Retreat, Sleeps 6
LocationOutdoor spacesKitchen

Waterfront Cottage at Ketners Mill Arena-2
ValueLocationAccuracy
Cabin rentals with a kayak

The Cabin
LocationComfortFamily

Lillypad Cove at The Retreat at Water's Edge
Outdoor spacesLocationLayout

Scenic Cabin Escape, Monteagle TN

Cabin Escape w/ Fire Pit, Monteagle

Atypical Cabin in Clifftops near Sewanee

Cabin at Normandy Lake
LocationOutdoor spacesGetting around

Vinay's Valley Adventure at The Retreat
Outdoor spacesValueComfort

Seq River 2BR Cabin - newly remodeled. Tiny home 1
Outdoor spacesLocationPets
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 | $439 NZD | $450 NZD | $460 NZD | $533 NZD | $618 NZD | $577 NZD | $606 NZD | $451 NZD | $439 NZD | $536 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
- Coolidge Park
- South Cumberland State Park
- Point Park
- Hunter Museum of American Art
- Chattanooga Zoo
- Raccoon Mountain Caverns & Campground
- Old Stone Fort State Archaeological Park
- Huntsville Botanical Garden
- Creative Discovery Museum
- Cathedral Caverns State Park
- Lowe Mill Arts And Entertainment
- Burritt on the Mountain
- Cumberland Caverns
- Discovery Center
- Chattanooga Whiskey Experimental Distillery
- Barfield Crescent Park
- Henry Horton State Park
- Von Braun Center, North Hall
- Tennessee River Park





