Family-friendly holiday rentals in Winchester

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, 89 reviews

Meadow View Retreat

Enjoy your stay at Meadow View Retreat with a beautiful view of the farm from the peaceful, serene back yard. We have a 72 acre farm and a family business located walking distance from the airbnb where you can grab a coffee, a bite to eat + stroll around the greenhouses! This 2 BDR house is the perfect stay for families, couples getaway or business trips. Conveniently located in Winchester, a short drive to the beautiful historic downtown Winchester, Tim’s ford Lake and Sewanee University.

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.

4.97 out of 5 average rating, 64 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

Home in Lynchburg, Moore County

A private dock extends into the calm waters of Tims Ford Lake, surrounded by lush greenery and gentle hills. Bright blue skies with scattered clouds reflect on the serene surface, enhancing the peaceful natural landscape.

Lakeside Family Escape-Modern Log Home; Pvt. Dock

Escape to our secluded lakeside retreat, overlooking a tranquil cove and featuring peaceful water views, modern accommodations and appliances, stylish interiors, a game room and plenty of room for making family memories. Enjoy breathtaking lake views from our 2 spacious decks, swim or fish off our private dock, or explore the stunning cove views on a kayak. Rent a boat or jet ski nearby, play a round of golf or visit the world-famous Jack Daniel's Distillery and the Lynchburg town square.

5.0 out of 5 average rating, 106 reviews

5.0 out of 5 average rating, 71 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, 121 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.

4.95 out of 5 average rating, 129 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 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, 42 reviews

Sunset Cottage +Dock on Tims Ford Sleeps 12

Welcome to Sunset Cottage, a spacious and serene lakeside escape nestled in the heart of Winchester. Located less than a mile from the town square, this charming cottage offers both the tranquility of lakefront living and the convenience of nearby dining and shopping. Relax as you take in breathtaking sunset views from the back covered porch. With a private boat dock, you can easily set out for a day on the water. Designed for comfort and relaxation, Sunset Cottage is the ideal getaway.

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, 124 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 :)

5.0 out of 5 average rating, 109 reviews

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.

Home in Tullahoma

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 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.

4.96 out of 5 average rating, 69 reviews

Grand Lakeview: Double decker dock, Fire Pit, Spa

Escape to the Captain's Quarters, a charming lakeside sanctuary. Unwind in our multi-level retreat, featuring floor-to-ceiling windows, a gourmet kitchen, and serene master suites with enchanting lake views. Designed to accommodate large groups, this spacious home boasts six bedrooms, and offers a total of 11 beds, ensuring privacy and comfort. Indulge in the great outdoors with our private dock, a hot tub, and delightful amenities, all set against the backdrop of Tim's Ford Lake.

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, 134 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.

4.98 out of 5 average rating, 41 reviews

A modern kitchen area features light wooden cabinets and stainless steel appliances. A round dining table with black chairs is set with a decorative centerpiece. Natural light filters through a window, enhancing the neutral color palette of the space.

Flat in Winchester

Clean Lines and Simple Comfort

This 2 bed, 2 bath apartment duplex is located just two miles from Tims Ford Lake. Whether you’re in town for a weekend or an extended stay, this space offers everything you need for a relaxing and comfortable visit. Each room features a comfortable queen bed, fresh linens and ample closet space. The kitchen is stocked with cookware, stainless steel appliances, and a coffee maker for your morning brew. Book your stay and enjoy an experience that’s clean with a blend of style.

Popular amenities for Winchester family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 105 reviews

The exterior of a cozy house is surrounded by trees, featuring a well-maintained yard with a fire pit and four adirondack chairs arranged on gravel. A spacious porch with steps leads to the entrance, inviting relaxation in a natural setting.

Tiny home in Tracy City

Tiny Home w/ Firepit + Hot Tub + Canoe

4.85 out of 5 average rating, 726 reviews

A modern treehouse sits elevated among the trees, featuring a large deck with wooden chairs and a hot tub. A grill is positioned on one side, with lush greenery surrounding the structure, providing a sense of privacy and seclusion in a serene environment.

Treehouse in Monteagle

Scandinavian Treetop Bliss @ Terralodge

4.97 out of 5 average rating, 180 reviews

An A-frame cabin is nestled among tall trees, showcasing a modern design with large glass windows. A wooden deck surrounds the entrance, featuring a seating area with chairs and a fire pit. The outdoor area is partially landscaped with natural ground cover.

Cabin in Monteagle

Modern Monteagle A-frame with Hot Tub

4.98 out of 5 average rating, 388 reviews

Cabin in Coalmont

The Coalmont Cabin - Romantic Lakefront Escape

5.0 out of 5 average rating, 108 reviews

A firepit area is surrounded by Adirondack chairs, arranged in a circular formation on a flat surface near the calm waters of the lake. Lush greenery and trees frame the peaceful setting, with the serene water reflecting the surrounding nature.

Home in Tracy City

Lakefront w/ Hot Tub + Kayaks + Fire Pit

4.89 out of 5 average rating, 256 reviews

A serene lake scene features a boat silhouetted against a vibrant sunset, where rays of light filter through scattered clouds. The calm waters reflect the warm hues of the fading day, with distant tree-covered hills framing the horizon.

Cabin in Manchester

Fire Lake Lodge Volleyball, Hot Tub, Kayaks!

4.94 out of 5 average rating, 248 reviews

A bright living area features large windows allowing natural light to illuminate the space. A comfortable sofa is paired with a modern ceiling fan. A well-equipped kitchen island is positioned in the foreground, enhancing the open layout towards the inviting outdoor space.

Tiny home in Tracy City

Where Tiny Living Meets Big Lake Escapes

Treehouse in Beersheba Springs

A modern tree loft is set among lush greenery, featuring large windows that provide ample natural light. A spacious deck surrounds the structure, which includes a private hot tub and a swing. The contemporary design is complemented by natural wood accents.

Modern Treehouse Loft | Epic Views · Hot Tub

4.9 out of 5 average rating, 163 reviews

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 670 reviews

Farm stay in Dunlap

The Farmstay at Little Tail Farms

4.95 out of 5 average rating, 225 reviews

A spacious living room showcases wood-paneled walls and ceiling. Two comfortable sofas and an armchair are arranged around a wooden coffee table. Decorative pillows add color. Natural light filters through light-filtering shades on the windows, and a large framed photograph is displayed on the wall.

Cabin in Tullahoma

Cozy Cabin close to Tims Ford Lake & Jack Daniels

Cabin in Lynchburg, Moore County

A view from the porch reveals the serene waters of Tims Ford Lake, bordered by lush greenery. The railing is partially visible, with sunlight filtering through the trees, creating dappled shadows on the deck. A bird feeder hangs nearby, inviting wildlife.

Cozy Cabin on Tims Ford Lake

4.97 out of 5 average rating, 237 reviews

4.94 out of 5 average rating, 294 reviews

A welcoming porch area features vibrant red flooring, complemented by a metal table and chairs. A vintage mailbox stands prominently, while a grill and a chiminea add to the rustic charm. Potted plants are placed nearby, enhancing the outdoor living space.

Cabin in Estill Springs

Holliday Hide Away

4.98 out of 5 average rating, 245 reviews

A charming black cottage nestled among tall trees is visible. The entrance features a small deck with steps leading to the door. A kayak rests on the ground nearby, and seating areas can be seen on the gravel pathway, surrounded by lush greenery.

Tiny home in Tracy City

2BR Nature Getaway in Tiny Home w/ Lake access

4.94 out of 5 average rating, 110 reviews

The exterior showcases a charming house with large windows and a spacious wooden deck. Outdoor seating is arranged on a gravel surface, illuminated by string lights overhead, contributing to a cozy atmosphere. Lush greenery surrounds the property, enhancing the sense of privacy.

Home in Sewanee

The Sewanee House: Main House + Guest Wing

Guest house in Lynchburg, Moore County

The exterior of the guest house is visible, featuring a covered porch with two chairs positioned on a stone patio. The grey siding contrasts with the wooden beams and red metal roof, while a driveway and a fenced yard can be seen in the background.

Country Guest House

4.96 out of 5 average rating, 327 reviews

Home in Lynchburg, Moore County

A welcoming front porch features multiple wooden rocking chairs arranged neatly along the covered area, with a central entryway leading to the home. The porch is framed by wooden beams and offers a view of the expansive lawn and nearby structures.

TN Fire 3 bedroom 2 bath beautiful new home

4.96 out of 5 average rating, 230 reviews

Family-friendly home rentals with a pool

4.93 out of 5 average rating, 132 reviews

The cabin is situated amidst lush greenery, featuring a sturdy wooden deck supported by stone pillars. Large windows are framed by natural wood, allowing sunlight to illuminate the rustic facade while the surrounding trees enhance the tranquil atmosphere.

Cabin in Tullahoma

Private lakefront log cabin w/dock & hot tub

5.0 out of 5 average rating, 109 reviews

A shipping container home is surrounded by lush trees, featuring large windows that offer views of the forest. Natural light filters in, illuminating the interior space, which is thoughtfully designed to blend with the outdoor scenery.

Treehouse in Sewanee

Private Treehouse Retreat! Sauna|Hot Tub|Pool

4.99 out of 5 average rating, 105 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

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.

4.93 out of 5 average rating, 15 reviews

The Perfect Getaway

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, 51 reviews

The Modern Mainstay at Barefoot Bay

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

Superhost

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.

4.88 out of 5 average rating, 50 reviews

Luxurious New Build LakeHouse Tim’s Ford 4BR4Bath

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.