Holiday rentals in Winchester

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!

Chalet 638 - state park, golf & The Caverns

Short walk to a state park with golfing. This first floor living space has a kitchen, walk-in closet, large wood fireplace, workout equipment, washer/dryer, grill, fire pit and lots of space. Old Stone Fort Archeological Park with multiple hiking trails, fishing, canoeing and a $9 a round golf course are seconds away. Close to I-24 this centrally located Tennessee property gives equal access from Nashville to Chattanooga. Explore parks, vineyards, distilleries and Tennessee history from here.

Tiny House

You will feel right at home in this adorable Tiny Home with RV Hookups! This picture-perfect little cottage has a bedroom with queen size bed, full bath with tile walk-in shower, full kitchen with all of the amenities, and living room with queen size sleeper sofa. The back porch offers peace, quiet, and spectacular mountain views. This property is super convenient to Tims Ford Lake, The Caverns music venue, Jack Daniels Distillery, University of the South, and historic downtown Winchester.

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.

The Nest at The Retreat @ Deer Lick Falls

The Retreat offers a cozy cottage for down time & you have the option to hike trails down to falls area, socialize with other guests or sit and have your own Fire in our fire pit on the property and just relax! Local Restaurants minutes away, lake access 10 minutes away with beautiful woodsy setting perfect for getting away from the hustle of everyday life! Covered patio for relaxing and you can eat outdoors with a grill guests can use and a fully equipped kitchen if you choose to cook.

The Hangout on Heath Lane

Enjoy a peaceful experience at this centrally-located home. The Hangout is half a mile from the beautiful Twin Creeks Marina and 1 mile to historic downtown Winchester! Other local attractions include: -Grab a coffee and enjoy a tasty breakfast or lunch at Walnut Hill Coffee Shop -For a delicious, upscale dinner, be sure to visit Filo's Tavern -Head out for a tour and tasting at Jack Daniels Distillery -Grab some tickets to the Cavern's for a memorable concert experience.

Cozy Cabin close to Tims Ford Lake & Jack Daniels

A cozy cabin awaits you located close to Tim's Ford Lake-1/2 mile from Holiday Landing Marina & Blue Gill Restaurant. Lynchburg, home to popular Jack Daniel's Distillery-only 12 miles away; Nashville-90 mins. Made from handcrafted red cedar, you will be met with a woodsy aroma when entering. Special touches can be found throughout including Jacuzzi tub! Truly a unique wooded cottage, equipped to ensure a relaxing getaway. Pet friendly with an additional pet fee.

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!

Homestead Haven

Enjoy your stay at Homestead Haven with a beautiful view of the farm. We have a 72 acre farm and a family business located walking distance from the airbnb. Take a short stroll down the hill to see the lovely plants and meet your host! This 2 bedroom guesthouse is the perfect stay for you and your loved ones. Conveniently located in Winchester, a short drive to the beautiful historic downtown Winchester and Tim’s ford Lake!