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 out of 5 average rating, 53 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

A spacious outdoor deck features a wooden dining table and chairs, overlooking a serene lake. The calm water reflects the colors of the sunset, surrounded by trees. A stone fire pit is visible, enhancing the tranquil setting.

4.99 out of 5 average rating, 101 reviews

Best Views on Lake, TIki Hut, Boat Rental + More

If you are looking for the perfect getaway to a luxury lake home that has countless amenities and postcard like views then look no further! This newly renovated lake front home boasts the best views on the lake, tiki hut, multiple outdoor decks, covered patio, hot tub, game room, theatre, kayaks, SUPs and plenty more! We even have a 2022 Crest tritoon with a 200 HP motor that is available to rent for experienced boaters! This is truly a one of kind property. We look forward to serving 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, 127 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 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, 107 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 out of 5 average rating, 20 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 out of 5 average rating, 40 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.

A modern structure features a sleek black exterior with wooden shutters. A covered porch is highlighted by two chairs and a potted plant, inviting relaxation. Lush greenery surrounds the home, providing a serene outdoor environment.

5 out of 5 average rating, 56 reviews

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.

4.99 out of 5 average rating, 134 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, 137 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, 66 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.

4.98 out of 5 average rating, 291 reviews

The exterior of a modern cabin is showcased at sunset, featuring a metal roof and large windows. The structure is surrounded by greenery and dramatic rock formations, with warm lights illuminating the porch area, creating a welcoming ambiance facing the Tennessee River and mountain views.

Home in Chattanooga

Our Catty Shack

Oliver and Lacey (the cats) would love to welcome you to Our Catty Shack! ***NOTE: Our Catty Shack comes WITH indoor/outdoor CATS*** This spiritual retreat is nestled between imposing ridgelines, abuts a state forest, and faces the powerful Tennessee river. Enjoy dramatic sun and moon rises. Luxuriate in the hot tub. Feast your eyes on the views. Only 15 minutes to downtown Chattanooga - with the peace of the country - have it all here.

5 out of 5 average rating, 103 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.

Popular amenities for Winchester house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.74 out of 5 average rating, 23 reviews

Lakeside Luxe | Lake + Pool Access

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, 24 reviews

TC Easy Breeezee

5 out of 5 average rating, 15 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, 12 reviews

The Old Fashioned w/ lake view & FREE pontoon!

4.88 out of 5 average rating, 48 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

4.9 out of 5 average rating, 21 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

4.93 out of 5 average rating, 59 reviews

Home in Chattanooga

Cliffside Infinity Pool • Hot Tub • Epic Views

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, 35 reviews

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

Weekly house rentals

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!

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, 70 reviews

Whiskey Trails Cottage

5 out of 5 average rating, 37 reviews

A modern home is set against a backdrop of leafy trees, featuring extensive glass walls that reflect the surrounding landscape. A spacious deck extends from the structure, supported by sleek pillars, with several outdoor seating options positioned for relaxation.

Home in Monteagle

"A Modern Vue"-Luxury-Hot Tub-Arcade

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.

5 out of 5 average rating, 8 reviews

Tennessee Whiskey -Cozy Screened Porch + Fireplace

4.91 out of 5 average rating, 23 reviews

Home in Estill Springs

Aqua-dream

A spacious private dock extends over the water, featuring a covered section for shade. Wood platforms provide ample space for seating, complemented by a ladder for easy access to the lake. Surrounding greenery enhances the serene lakeside environment.

4.99 out of 5 average rating, 77 reviews

Best Home on Tims Ford - Private Dock - Hot Tub

5 out of 5 average rating, 11 reviews

Home in Whitwell

A-mazing new lakefront cabin

5 out of 5 average rating, 49 reviews

On Water w/ Private Dock, Entire Home, sleeps 14

Private house rentals

4.95 out of 5 average rating, 41 reviews

The property is set along a scenic creek, featuring a multi-level staircase leading down to the water's edge. Surrounding trees provide a natural backdrop, while a spacious outdoor area offers seating and recreational options. A well-maintained lawn is visible alongside the building.

Home in South Pittsburg

Waterfront•Hot Tub•Arcade•Sweetens Cove Lodge

4.8 out of 5 average rating, 143 reviews

Charming Retreat 5 Min to Tims Ford Lake; Sleeps 8

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 out of 5 average rating, 66 reviews

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

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, 102 reviews

Emerald Cove Cottage

A bright sunroom with panoramic lake views features large windows allowing natural light to fill the space. A comfortable white sofa is accompanied by two rattan chairs, creating a relaxing atmosphere. A ceiling fan maintains airflow, and light wood flooring enhances the openness.

4.97 out of 5 average rating, 77 reviews

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

5 out of 5 average rating, 35 reviews

Serene Lake House Retreat with New Golf Cart

5 out of 5 average rating, 78 reviews

Home in Monteagle

Mountain Mist - HOT TUB & King bed w/ fire pit

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.