House holiday rentals in Winchester

5.0 out of 5 average rating, 66 reviews

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

Lush green trees frame a peaceful view of the lake, where a floating dock is visible alongside moored boats. A paved pathway leads down to the water's edge, surrounded by manicured grass and natural stone. Clear blue skies reflect off the calm surface of the water.

4.94 out of 5 average rating, 119 reviews

Beautiful Tims Ford lakefront home

Beautiful 3 level lake front home right by the water with no steps to the dock. Plenty of room for large groups of people and great for families with kids. Five bedrooms with a bonus room that has plenty of extra beds. Located less than a mile from public boat ramp. Located in quiet cul-de-sac, on a cove with no wake next to the main channel. If there are any dates that are blocked off that you want please message us because we may have some blocked off dates that we can open up for you.

An outdoor seating area features blue and white lounge chairs arranged around a central fire pit. The shaded porch swing offers a serene view of the lake, framed by lush greenery. The dock and numerous boats can be seen in the background.

4.96 out of 5 average rating, 128 reviews

Private dock/gazebo on quiet cove. Tims Ford Lake!

Indulge in the tranquility of Tims Ford Lake, TN! Our exquisite 5-star cottage, just 6 miles from Tims Ford State Park/Marina, beckons you to unwind. Conveniently situated 18 miles from Tullahoma and 8 miles from Winchester, our boat-friendly haven features a private dock and a circular drive. Minimum rental age: 25. Ensure a seamless stay by signing our legal Rental Agreement and presenting a government-issued ID. Book now for a worry-free lakeside escape – your perfect retreat awaits!

A modern guesthouse is set against a backdrop of lush greenery and a serene pond. The building features dark siding with wooden accents, while a well-maintained lawn leads to a gravel path. Bright blue skies and scattered clouds provide a peaceful atmosphere.

4.98 out of 5 average rating, 84 reviews

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!

A modern two-story house features a green exterior with white trim and a welcoming porch. An American flag hangs from the porch, and soft outdoor lighting illuminates the entrance. A driveway leads to a garage, with trees providing a natural backdrop.

5.0 out of 5 average rating, 109 reviews

Lakeside Retreat at The Reserve w/ Golf Cart

Beautiful lakeside home on Tim's Ford Lake! Short Walk or Golf Cart ride to Blue Gill Grill & Holiday Landing Marina. Boat Parking on the Driveway during your stay! First Floor: Master Bed with Full Bath, Dining Room, Living Room, Kitchen (Fully stocked with basic spices and cooking utensils). Outside Patio with Fire Place and seating. Second Floor: BR 2- King Bed. BR 3 Queen Bed, Loft Space, Sectional Couch, Pull out Queen. *No Smoking *Max 10 Guest *Front Door Security Cam*

A serene outdoor space features four red Adirondack chairs arranged around a circular stone fire pit. The scene is illuminated by the warm glow of the setting sun, casting soft light through the surrounding trees and reflecting on the tranquil lake in the background.

4.9 out of 5 average rating, 132 reviews

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.

The exterior of a modern custom home is displayed, featuring a combination of white and blue siding. A spacious green lawn surrounds the property, while a circular seating area with chairs is positioned in front of the home, inviting outdoor relaxation.

5.0 out of 5 average rating, 26 reviews

Barefoot Dreams

Barefoot Dreams is a newer custom lake home vacation rental in the gated community of Barefoot Bay on Tims Ford Lake in Winchester TN. This luxury lake house rental is perfect for families and groups seeking a Tims Ford Lake cabin, waterfront getaway, or Tennessee lake vacation home. Enjoy stunning water views, modern design, and an open-concept layout. Ideal for boating, fishing, swimming, and lakefront relaxation. A peaceful yet fun-filled family vacation rental on the lake.

A contemporary two-story home showcases a light-colored exterior with a gabled roof and a covered front porch. A balcony extends from the upper level, complemented by a ceiling fan. The landscaped area features low shrubbery and a paved pathway leading to the entrance.

5.0 out of 5 average rating, 49 reviews

The Modern Mainstay at Barefoot Bay

Welcome to The Modern Mainstay, your stylish retreat by the shores of Tims Ford Lake! This pet friendly contemporary home is just 1/2 mile from the historic downtown square where you can enjoy doing a bit of shopping or dining. Or sit on the front porch with lake views, and take in the serene surroundings. Take a dip in our lakefront community pool. Enjoy access to the lakefront common area for fishing, swimming in the lake, and relaxing by the fire pit with a glass of wine.

4.99 out of 5 average rating, 144 reviews

Home in Decherd

"Near Caverns and Sewanee 2-bedro/2-bath w/EV char

2 bedroom, 2 full bathrooms, totally remodeled home with a large fenced back yard and fully equipped modern kitchen. Easy drive less than 7-mi to Sewanee, and just 10-miles/ 10-12 min to The Caverns. The "Farm View" house offers country views with privacy. A serene place to relax, unwind and retreat while enjoying pastures and country views. "EV/Tesla wall charger", Starlink internet w/ streaming tv. Only 3.5 miles off 1-24 exit 127, Pelham, Winchester.

4.94 out of 5 average rating, 71 reviews

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.

5.0 out of 5 average rating, 117 reviews

A spacious screened porch features comfortable seating, including a cozy sofa and armchair, overlooking a serene lake view. Large glass panels invite natural light, while a wooden deck extends outside, providing access to the lakefront and enhanced outdoor experience.

Home in Tracy City

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.

A modern house exterior is depicted, featuring a gable roof and a mix of vertical and horizontal siding. Black window frames and decorative wood accents provide contrast against the light-colored façade. A paved driveway leads to a single-car garage, with a white vehicle parked nearby.

4.88 out of 5 average rating, 41 reviews

Luxury 3BR lakeside escape

Discover serenity at New Latitude in Twin Creeks Village! Nestled near the picturesque shores of Tim’s Ford Lake, our 3-bedroom, 3-bathroom retreat offers a haven for relaxation and rejuvenation. Enjoy the scenic charm of Twin Creeks Village, where tranquility meets luxury just moments from Twin Creeks Marina. Indulge in lakeside living at New Latitude. Book your getaway now and experience the beauty and calm of Tim’s Ford Lake!

Popular amenities for Winchester house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 103 reviews

A spacious timber frame home is situated on a hillside overlooking a lush valley, with mist rising from the trees. A pool is positioned near the house, surrounded by a manicured lawn. The outdoor area includes a fire pit, enhancing the tranquil atmosphere.

Home in South Pittsburg

Cozy Cabin in the Clouds

The exterior of a modern two-story home is displayed, featuring a light-colored facade with black accents. A garage door complements the structure, while a decorative blue door offers an inviting entrance. The manicured lawn extends towards the serene lake visible in the background.

5.0 out of 5 average rating, 60 reviews

Lakefront Haven | Hot Tub | Kayaks, Firepit

Two kayaks in vibrant orange and blue are positioned on a concrete patio, adjacent to a green lawn. Trees with budding leaves and flowering branches frame the serene lakeside view. A covered deck above provides shade, enhancing the inviting outdoor space.

4.91 out of 5 average rating, 45 reviews

Luxurious New Build LakeHouse Tim’s Ford 4BR4Bath

Superhost

The entryway features a welcoming porch with two comfortable seating areas, one composed of wooden rocking chairs and another wicker chair. A decorative welcome mat greets guests, while a handcrafted wreath adorns the door, inviting all into the cozy interior beyond.

4.79 out of 5 average rating, 28 reviews

Lakeside Luxe | Lake + Pool Access

5.0 out of 5 average rating, 25 reviews

Tennessee Pearl: lakefront-amazing views-lake toys

A three-story home with a light-colored exterior and brown shutters is showcased. Two wooden garage doors complement the design. A neatly landscaped front yard features two evergreen shrubs beside the entrance. Large windows allow plenty of natural light into the living spaces.

4.75 out of 5 average rating, 12 reviews

The Mimosa @ Twin Creeks Resort w/ free pontoon!

The living area features a large sectional sofa in a soft blue hue, arranged around a dark wooden coffee table. A stone fireplace stands against a white-painted wall, with a television mounted above it. Windows provide views of the surrounding lake, allowing natural light to brighten the space.

4.87 out of 5 average rating, 39 reviews

EASY PEASY on Tim's Ford Lake, golf cart, pool

A spacious two-story brick house is framed by green lawns and neatly trimmed bushes. Large windows with black shutters line the front, and a covered entrance is visible on the left. A clear blue sky serves as the backdrop, enhancing the home's inviting presence.

4.92 out of 5 average rating, 13 reviews

The Perfect Getaway

Weekly house rentals

5.0 out of 5 average rating, 26 reviews

Lakeside Manor Retreat

5.0 out of 5 average rating, 14 reviews

Lakefront Lodge

A covered porch features comfortable seating arrangements, with two cushioned chairs positioned around a circular wooden table. A spacious grassy yard extends beyond the porch, framed by lush greenery and trees. The tranquil waters of Tims Ford Lake can be glimpsed in the background.

5.0 out of 5 average rating, 39 reviews

Sunset Cottage +Dock on Tims Ford Sleeps 12

The single-story home features a light-colored exterior with a gabled roof. A concrete driveway leads to the garage. Surrounding the house are well-maintained lawns with small trees and shrubs, set against a backdrop of open fields and a clear blue sky.

4.95 out of 5 average rating, 77 reviews

Extend your Summer in TN~Golf~Fish~Hike Great deal

5.0 out of 5 average rating, 10 reviews

Water's Edge - Lakeside retreat

The front entrance of the cottage features a welcoming green door framed by white siding and a covered porch. A potted plant adds a touch of greenery beside the entrance, and a stone pathway leads to the door, inviting guests inside.

4.92 out of 5 average rating, 51 reviews

Cottage on Cedar

The entrance features a wooden door with multiple glass panels, complemented by a dark brown welcome mat and a tall, rustic sign that reads 'WELCOME.' The porch is framed by vertical siding and surrounded by greenery.

4.98 out of 5 average rating, 40 reviews

A quiet getaway.

The exterior of a two-story blue house is showcased, featuring a peaked roof and white trim. A welcoming red front door is framed by large windows, and landscaped beds with shrubs are neatly arranged along the foundation.

5.0 out of 5 average rating, 70 reviews

Luxury Living at Tim's Ford Lake, w/ Golf Cart

Private house rentals

Superhost

5.0 out of 5 average rating, 4 reviews

Spring Fun, Fishing, & Fire Pit. Cove Sweet Cove!

A close-up view features a stylish light fixture beside a dark, round table. The background showcases a textured wallpaper with bold, black plant motifs. A soft white bed is highlighted, accompanied by a decorative pillow with black and white fringe.

5.0 out of 5 average rating, 23 reviews

Location, location, location!

5.0 out of 5 average rating, 39 reviews

Serene Lake House Retreat with New Golf Cart

The kitchen features modern stainless steel appliances, including an oven and microwave, set against green cabinets. A spacious granite countertop with a farmhouse sink is complemented by decorative floating shelves displaying dishware and plants, while a patterned backsplash adds visual interest.

4.87 out of 5 average rating, 55 reviews

1940 Renovated Cottage Near Square/Lake Summer Fun

An aerial view of a lakefront property features a large house surrounded by well-maintained greenery. A private dock extends into the water, equipped with seating areas, and a pathway leads from the house to the dock, creating a harmonious outdoor space.

5.0 out of 5 average rating, 73 reviews

Tims Ford lakefront, hot tub, dock & boat ramp

A lively scene unfolds at the dual-level private dock, where guests enjoy various water activities. Individuals are seen jumping from the dock into the lake, while others paddle nearby. Bright umbrellas provide shade, and boats rest on the water, enhancing the vibrant atmosphere.

4.95 out of 5 average rating, 65 reviews

Grand Lakeview: Double decker dock, Fire Pit, Spa

5.0 out of 5 average rating, 10 reviews

The Cozy Cottage at Tim's Ford Lake (Sleeps 6)

A golf cart is parked in the driveway in front of a cottage, featuring a covered porch with two blue chairs. The cart is equipped with comfortable seating, black detailing, and all-terrain tires, designed for easy access to the nearby marina.