House holiday rentals in Winchester

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

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 • Hot Tub • Fantastic community pool for the hot summer days • Screened in, heated porch with TV and sound system • Kayak, 2 Paddleboards 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

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*

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, 48 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, 143 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, 70 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.

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!

4.99 out of 5 average rating, 107 reviews

Home in Estill Springs

Waterfront Access | Lake Views | Dock | Pool Table

Indulge yourself with private waterfront access and stunning million dollar views in this sunny slice of paradise. Experience our waterfront lounge, on-site boat dock, outdoor fireplace, pool table, mini golf putting green, tiki lamps, luxurious jacuzzi tub with spa jets, outdoor dining, sleepy sunroom, charcoal grill, 4K smart TV's, and fully inspired gourmet chef's kitchen. Welcome to "Lakeside Paradise."

Popular amenities for house rentals in Winchester

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

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, 44 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

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

5.0 out of 5 average rating, 25 reviews

Tennessee Pearl: lakefront-amazing views-lake toys

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, 38 reviews

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

An open living space features two patterned armchairs positioned across from a spacious sofa. The area is well-lit by multiple ceiling fans and recessed lighting. Large windows provide ample natural light and scenic views, while a dining area with high-backed stools is visible in the background.

5.0 out of 5 average rating, 14 reviews

The Old Fashioned w/ lake view & FREE pontoon!

A private salt-water pool is surrounded by a spacious patio. Several lounge chairs offer comfortable seating options, complemented by red umbrellas providing shade. A barbecue grill is visible nearby, and a low white fence encircles the area, with a backdrop of residential buildings and a clear sky.

4.93 out of 5 average rating, 29 reviews

TC Easy Breeezee

Weekly house rentals

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, 76 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 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.

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, 38 reviews

Sunset Cottage +Dock on Tims Ford Sleeps 12

5.0 out of 5 average rating, 25 reviews

Lakeside Manor 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

Superhost

5.0 out of 5 average rating, 4 reviews

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

Private house rentals

A green A-frame cabin is surrounded by trees, featuring a welcoming front porch with two chairs. A stone pathway leads to the entrance, and an American flag is displayed proudly nearby. The outdoor area showcases well-maintained grass and landscaping, enhancing the cabin's natural setting.

4.98 out of 5 average rating, 49 reviews

A-Frame on Tims Ford Lake Private Boat Dock w/slip

5.0 out of 5 average rating, 10 reviews

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

5.0 out of 5 average rating, 39 reviews

Serene Lake House Retreat with New Golf Cart

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 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!

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

5.0 out of 5 average rating, 44 reviews

A serene view of the lake house is captured from across the water, revealing its modern architecture and spacious deck. Lush greenery surrounds the property, and a private fishing dock extends into the calm lake, reflecting the house and surrounding trees.

Home in Tracy City

The Little Lake House @The Retreat at Waters Edge