Vacation 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.

Luxurious New Build LakeHouse Tim’s Ford 4BR4Bath

Fully furnished - a unique Tim’s Ford 3 level house! 4 bedrooms LakeHouse with 3 decks, theatre room, 2 furnished kitchens. Free Kayaks with jackets. Soak in the Sun or feel the breeze from the three decks - with breathtaking views. Next door Swimming pool n boat ramp. Twin creek Marina n restaurant - 5 mins drive. Downtown Winchester restaurants - 5 min drive. 3 cars parking + guests parking. Wheel chair ramp access. Family n friends celebrate lake life at Lakehouse! Pls declare your pets

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!

Moonwakes & Mimosas: Adventure and Convenience

* SWEETENS COVE GOLF CLUB IS ONLY 3 MINUTES AWAY! Whether you are looking for a base camp for your outdoor adventures or a low key spot to relax between wedding events or festivals, we have you covered! Not even one mile from I24 and right off the main road through town, we offer nature and convenience. Book your stay at Moonwakes & Mimosas and discover the wealth of natural beauty and outdoor fun our little corner of the world offers. Follow us on social media at Moonwakes and Mimosas!

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.

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.