Holiday rentals with a patio in Winchester

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.

Location, location, location!

No detail has been left undone when it comes to cleanliness, decor, or amenities. Tims Ford Boat Launch <1/4 mile, walk to Twin Creeks, Walk to historic Winchester square (< 1mile) where you can enjoy several dining/shopping options. Hike the mountains, tour Sewanee, Jack Daniels or Dickel, boat at Tims Ford, float the Elk, or just relax at this oh so quaint home. The location is also convenient for concerting at The Caverns. If you are tired of boring and unclean rentals, look no further!

The Hangout on Heath Lane

Welcome to The Hangout on Heath Lane! Just 1/2 mile from Twin Creeks Marina and 1 mile from historic downtown Winchester, our new 2-bedroom retreat is the perfect home base for lake weekends, concerts at The Caverns, Jack Daniel's tours, and family getaways. Enjoy modern comforts, sparkling cleanliness, and the small-town charm that keeps guest coming back! We also suggest: -Coffee & breakfast or lunch at Walnut Hill Coffee Shop -For a delicious, upscale dinner, go visit Filo's Tavern

Meadow View Retreat

Enjoy your stay at Meadow View Retreat with a beautiful view of the farm. We have a 72 acre farm and a family business located walking distance from the airbnb. We are a 10 minute drive to Tim’s Ford Lake, Twin Creeks Marina & historic downtown Winchester + 15 minutes from University of the South. This 2 bedroom guesthouse is the perfect stay for you and your loved ones. Enjoy the private, quiet back porch with a view of the pond and the farm. Beautiful sunrise + sunset views too!

1940 Renovated Cottage Near Square/Lake Summer Fun

WELCOME to this beautiful, newly renovated COTTAGE near the Winchester Square and Tim's Ford Lake. This Historic Home, built in 1948 is full of CHARACTER but yet modern and stylishly furnished. Within walking distance to the Winchester Square and just 1 mile from Twin Creeks Marina this beautiful home is convenient, comfortable, and welcoming for all guests. This is the home that you have been looking for that is BUDGET friendly but also packed with AMENITIES in the perfect location!

Modern Monteagle A-frame with Hot Tub

Welcome to Camp Mae, a Scandinavian inspired A-Frame stay in Monteagle, TN. Minimalist designed yet elegant, offering the perfect escape- minutes from the Fiery Gizzard hiking trail and Monteagle. Relax in the hot tub or gather around the fire pit. For eco-conscious travelers, we provide an electric car charger. Experience seclusion of the mountains while only minutes from world class hiking, local restaurants and shops. This retreat harmonizes luxury with nature in a serene setting.

Restful Modern Tiny House Nestled into the Plateau

Welcome to the Fringeless Orchid Tiny Home! Vacation time is precious. That’s why The Fringeless Orchid was created. Retreat from everyday life to mountain time in Tracy City, Tennessee. Tucked into a wooded lot with a creek running through the back, you’re sure to leave “normal” life at home while you enjoy time away. Breathe-in the mountain air as you enjoy our two-bedroom, two-bathroom tiny house designed with ultimate relaxation and synchronicity with nature in mind.

Honeysuckle Hill Tiny Home - Fire Pit Pet Friendly

Welcome to Honeysuckle Hill - your cozy retreat in the peaceful Water’s Edge community of Tracy City, TN, just minutes from Monteagle and Sewanee. Perfectly tucked into the South Cumberland Plateau, this area offers the best of both worlds: endless outdoor adventure and small-town charm with great restaurants and unique shopping nearby. Inside, Honeysuckle Hill invites you to slow down and savor Southern charm with high ceilings, abundant natural light, and classic decor.

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.

Basecamp Retreat TimsFordLake

Welcome to Basecamp Retreat! Modern lake luxury on Tims Ford Lake. This 3-bedroom, 2.5 bath cozy retreat, located in the gated community of Barefoot Bay, is the perfect home base for your visit. Offering modern comforts and convenience in a prime location with picturesque lake views, Basecamp provides a comfortable and inviting space to relax and recharge. Located 2 miles from Twin Creeks Marina & Resort and 1 mile from downtown Winchester.

Window Rock | Jackson Point · Modern Bluff Retreat

A design-led retreat on seven private acres above the valley. Two bedrooms, 2.5 baths, panoramic views. Near Sewanee on Tennessee's Cumberland Plateau — close to MICHELIN-recognized dining, world-class hiking, and some of the darkest skies in the Southeast. Soak in the cedar tub. Put a record on the vinyl station. Sit on the deck at sunset and forget to check your phone. See more images and videos on our social media: @windowrockmodern.

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.