Holiday rentals with a kayak in Winchester

Winchester's Premier Downtown Loft!

Escape to The Heritage Lofts where you'll find all of the comforts of home right off the Winchester square! You'll immediately fall in love with its classic, yet contemporary styling. This spacious apartment showcases an open kitchen and living area. Its ample natural light will buoy your spirits and it boasts plenty of room to stretch your legs after a busy day taking in everything that the square has to offer. Rest well in a king size bed and enjoy this charming piece of Winchester's heritage!

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.

Cozy Lake Cottage W/Pool, Hot Tub,Kayaks, SUPs

Enjoy lake living at one of the newest lakefront neighborhoods on Tim's Ford Lake. This cozy cottage is in a beautiful gated community and has lake views from the front porch. It is only a 1 min walk to the community pool overlooking the lake and direct lake access for kayaks and paddleboards that we include for you! This beautiful home also boasts a hot tub, fire pit, and game room for your family to enjoy! You are also centrally located and only 5 min from Twin Creeks Marina and downtown!

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!

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.

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.

Cozy tiny home ☆Sleeps 4 w/ great outdoor space

Relax & unwind at our tiny home located in Tracy City Sleeps 4-Queen bed in private bedroom & upstairs loft Covered deck w/ gas firepit Campfire in backyard Electric fireplace inside Outdoor obstacle course for kids Fully stocked kitchen 3 Tv's, DVD players & DVD's Fishing poles Great restaurants and shops Bike and hiking trails nearby Kayak & canoe rentals Gas grill 90 min from Nashville, 45 min from Chattanooga, & 15 min from the University of the South in Sewanee.

Peaceful Getaway on Kayak Way – Winchester

Welcome to Southern Reserve – One of Twin Creeks' Few True Waterfront Homes! Located in the heart of Winchester, TN, ‘Southern Reserve’ is a rare gem in the Twin Creeks community—one of the very few homes that sits directly on the water at beautiful Tims Ford Lake. This modern 6-bedroom, 5-bath retreat features two spacious master suites and a third lake-view king bedroom, making it perfect for multiple couples with kids seeking a shared, yet private, lakeside getaway.