Family-friendly vacation rentals in Winchester

Lakefront Haven on Tims Ford w/ Kayak and SUP

Welcome to Lakefront Haven! This home offers a seamless blend of comfort and luxury, providing a retreat for a lakefront getaway. • Lakefront property + beautiful views • Spa Getaway • Fantastic community pool for the hot summer days • Screened in, heated porch with TV and sound system • Kayak, Paddleboard and Peleton provided • Deck with gas Weber grill • Backyard firepit with chairs • Well equipped kitchen • Less than two miles from Twin Creeks Marina • Walkable to the downtown Square

Unbeatable Charm & Convenience On The Square!

Escape to The Heritage Lofts, just off of the thriving Winchester square. Just minutes from Tims Ford Lake, this fabulous newly-renovated apartment has it all! Stock up for your next adventure downstairs at Russells Outdoor and Trading Company then head next door to Walnut Hill for coffee and breakfast before setting out for the day. Grab a bite to eat at Jefferson's a few doors down and relax in the comfortable confines of your cozy king-sized bed. There isn't a more convenient spot in town!

Stayframe: designer getaway w/ private lake access

Welcome to our custom-built Aframe in the woods just 90 minutes from Nashville. This quiet retreat perched on the Cumberland Plateau gives you access to the hikes and waterfalls the area is known for, while offering an elevated guest experience. Enjoy the soaking tub, gas fireplace, fast wifi, Smart TV, well-appointed kitchen, and bluff views. Sewanee University, Cumberland Caverns, Fiery Gizzard, and Sweetens Cove are all within a short drive. Sorry, no parties, events, or photoshoots.

Holliday Hide Away

1200 sq. ft. very rustic converted pole barn. The floors are stained concrete and the walls are rough saw mill hewn poplar boards. Located on 3 acres of beautiful well kept property. It does not border the lake but is surrounded by Tims Ford Lake and less than 5 minute drive to 3 boat docks and launches. Close to restaurants, shopping venues, hiking trails, water falls and golfing. Pool table, cornhole set, board games & cards in cabin. Visit historic Franklin County and surrounding areas.

Rare Flat Lot w/Beautiful Views, Dock, Hot Tub

Escape to this charming lakeside retreat, where stunning sunsets and unbeatable water views await! Sitting right on the water, this cozy home offers a dock with a slip, two paddleboards, two kayaks, and a hot tub for ultimate relaxation. Dine outdoors by the lake, gather around the fire pit table, or enjoy the kid's game room with foosball and an arcade. With its vintage charm and unbeatable location, this is the perfect getaway for families and friends looking for lakefront fun!

Dock on Lake! Walk to Downtown Shops/Rest/Movies!

Charming, *Pet Friendly* well-loved 1950s lake house on Tim’s Ford Lake. Walking distance to grocery and downtown movie theatre, boutiques, restaurants and library. Near Twin Creeks marina/restaurant where you can rent boats. While here, you can swim at the dock; play darts, checkers or fuse ball; go out on the lake; walk to the Oldham Theatre; go hiking in Tim’s Ford State Park or nearby Sewanee; go to the Tullahoma drive-in theatre; or visit nearby Jack Daniel’s distillery.

Hot tub, game room, fire pit and a view!

This modern, Scandinavian style cabin, sits on 20 private acres at a 1360 ft. elevation. The style sets it apart from other cabins. It is 13 miles from The Caverns concert venue (about a 20 minute drive). The cabin is close to Sewanee, which has many hiking trails and is home to The University of the South (about 7 miles from our cabin/ a 16 minute drive.) Other local hiking and recreation options include the South Cumberland State Park and Tims Ford State Park.

Lovely Lake View Home at Twin Creeks Marina

This Craftsman-style, lake-view house is located in the private, gated lakeside community of Twin Creeks Village at scenic Tim's Ford Lake in Winchester, TN. It features an open floor plan with 4 bedrooms, 3 baths, game room, screened porch and huge deck overlooking the lake. Use the included golf cart to go to the swimming pools, marina, bar & grill or on-site convenience store. Information on boat & jet ski rentals are available at the marina shop.

Woodland Ct. Cottage

This one bedroom guesthouse is the perfect stay for you and your loved ones! Conveniently located in the heart of Tullahoma! Within walking distance of just about everything you need from grocery stores, restaurants, local coffee shops, and more! We are located just 20min from the famous Jack Daniels Distillery and 15 min from George Dickle! If you are interested in some nearby hiking be sure and check out Short Springs and Rutledge falls!