House vacation 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 out of 5 average rating, 56 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 out of 5 average rating, 58 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

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.

4.97 out of 5 average rating, 79 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 wooden dock extends over the tranquil water, featuring kayaks and paddleboards secured alongside. An upper deck with several chairs offers a relaxing space, while views of the lush surroundings create a calming atmosphere. The water sparkles under clear blue skies.

4.98 out of 5 average rating, 117 reviews

Lake Home, Dock, Theatre, Hot Tub, FirePit, Kayaks

Take it easy at this unique and tranquil getaway. This beautiful lake home is one of it's kind at Tim's Ford. The house is nestled in a quiet rural neighborhood with woods in the backyard. The dock is only a small golf cart ride away. Enjoy beautiful lake views at your own private dock! This house is equipped with an amazing home theatre system, game room, hot tub, fire pit, kayaks and plenty more amenities! Tim's Ford Dam is only one mile away and has a public boat launch for you :)

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 out of 5 average rating, 108 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, 129 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.

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 out of 5 average rating, 42 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.

5 out of 5 average rating, 19 reviews

Lakeside Manor Retreat

Enjoy your stay at this gorgeous modern style sanctuary, nestled on 2 acres near Tim’s Ford Lake. A private oasis, only 2 blocks from Twin Creeks Community & 6 blocks from Historic Downtown. Featuring gorgeous kitchen w/bar, wine fridge, ice machine, granite islands ,2 master suits with XL soaking tubs, 4 bedrooms, 3.5 baths, 7 TVs, air hockey & more! Sleeps 12. Plenty of parking. Message us with any questions. Thank you for your interest in Lakeside Manor Retreat

4.99 out of 5 average rating, 137 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.

The exterior view showcases a Craftsman-style house bordered by a spacious deck. A wooden pergola arches over part of the deck, enhancing the outdoor living space. The yard features manicured grass and is enclosed by a black fence for added privacy.

4.93 out of 5 average rating, 138 reviews

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.

4.94 out of 5 average rating, 67 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.

Popular amenities for Winchester house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.92 out of 5 average rating, 26 reviews

TC Easy Breeezee

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.

4.75 out of 5 average rating, 24 reviews

Lakeside Luxe | Lake + Pool Access

5 out of 5 average rating, 16 reviews

A wooden dock extends over the calm lake, with two Adirondack chairs positioned for lakeside relaxation. Kayaks in various colors are visible at the front, surrounded by lush greenery and trees that frame the serene water.

Home in Monteagle

Lakefront, 3 Boats + Pizza Oven, Gorgeous!

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 out of 5 average rating, 13 reviews

The Old Fashioned w/ lake view & FREE pontoon!

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 out of 5 average rating, 21 reviews

Barefoot Dreams

4.88 out of 5 average rating, 51 reviews

A charming home with a light-colored exterior is set amidst lush greenery. A spacious deck with seating options faces a stone patio surrounded by vibrant foliage, creating an inviting outdoor area. Large windows provide ample natural light, enhancing the connection to the surrounding nature.

Home in Sewanee

Forest Retreat: Poolside Bliss Close to Campus

4.91 out of 5 average rating, 23 reviews

The welcoming exterior of a two-story farmhouse is shown, featuring a front porch with seating options. Lush greenery and hanging plants frame the entrance, complemented by a neatly manicured lawn. The light-colored siding contrasts with the dark accents of the porch, creating a harmonious outdoors.

Home in Lynchburg

Private indoor pool & sauna

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.

4.86 out of 5 average rating, 36 reviews

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

Weekly house rentals

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 out of 5 average rating, 30 reviews

Sunset Cottage +Dock on Tims Ford Sleeps 12

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 out of 5 average rating, 23 reviews

Location, location, location!

5 out of 5 average rating, 43 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

5 out of 5 average rating, 14 reviews

Lakefront Lodge

A spacious covered dock extends over the tranquil waters, featuring two large swings for relaxation. Kayaks are positioned nearby, surrounded by lush greenery. Steps lead up from the dock to the home situated among the trees, creating a serene lakeside setting.

5 out of 5 average rating, 25 reviews

Lakeside Serenity: Cove Retreat

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.

4.86 out of 5 average rating, 51 reviews

1940 Renovated Cottage Near Square/Lake Summer Fun

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.

4.97 out of 5 average rating, 36 reviews

A quiet getaway.

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, 61 reviews

Grand Lakeview: Double decker dock, Fire Pit, Spa

Private house rentals

4.8 out of 5 average rating, 143 reviews

Charming Retreat 5 Min to Tims Ford Lake; Sleeps 8

4.98 out of 5 average rating, 50 reviews

Home in Sewanee

Whitetail Creek Lodge Close to Campus

The exterior of the home is highlighted by a white facade with teal shutters. Four rocking chairs are positioned on the porch, complemented by potted plants. A pathway leads to the entrance, framed by green trees providing a natural setting.

4.9 out of 5 average rating, 104 reviews

Emerald Cove Cottage

5 out of 5 average rating, 21 reviews

The exterior of the property features a traditional single-story home with a welcoming porch and a spacious front yard. A covered carport is adjacent to the house, providing shelter. Lush green trees frame the scenic view, enhancing the overall appeal of the property.

Home in Estill Springs

Timberhill Home-Walk to the Lake!

4.97 out of 5 average rating, 78 reviews

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

5 out of 5 average rating, 37 reviews

Serene Lake House Retreat with New Golf Cart

An open-concept area is featured, showcasing a rustic wooden dining table surrounded by stools. Modern pendant lights hang above, illuminating the space. A cozy seating area with a large TV is visible in the background, complemented by light-colored walls and warm wooden flooring.

5 out of 5 average rating, 73 reviews

Whiskey Trails Cottage

A charming two-story house features a blue and white exterior with a welcoming front porch. Two wooden rocking chairs sit invitingly on the porch. Lush greenery surrounds the property, complemented by a broad driveway leading up to the entrance.