Family-friendly vacation rentals in Winchester

4.86 out of 5 average rating, 211 reviews

A comfortable living area is observed, featuring a light-colored sectional sofa and a dark wooden coffee table. Large windows provide natural light, while a rustic dining table and chairs are visible in the background. Decorative wall art and assorted accents highlight the cozy atmosphere.

Cabin in Winchester

Private Dock - Best Cabin Tims Ford Lake

Great cabin located directly on Tims Ford Lake. Cabin has been updated and includes nice, well stocked kitchen as well as a deck (with grill). Enjoy our dock - fish, swim and use our two kayaks, paddle board and a canoe. Plenty of space to tie your boat up to our dock in a mostly private cove. Please read the guest access section for more details on lake access. Close to some great attractions - Jack Daniels Distillery (19 mi), Bonnaroo (25 mi), Univ. of the South (19 mi), Winchester (5 mi)

KitchenFamilyBathroom

5 out of 5 average rating, 100 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

Imagine sipping your coffee while watching the deer pass through 5 acres of forest from our steam sauna. Imagine enjoying a private marked path on property or hopping in your car to hike a 9 mile, 5 hour trail just 15 min from home, then recovering in the hot tub. If you want a private city escape, our shipping container treehouse is for you! PRIVACY NOTE: There are ZERO shared spaces, no on else on property. While we live in a 'neighborhood' you cannot see another home from our treehouse.

Indoor spacesFamilyHiking

5 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

KitchenIndoor spacesParking

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!

Indoor spacesKitchenGetting around

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, 122 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 :)

Indoor spacesFamilyNearby

4.96 out of 5 average rating, 171 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

Welcome to Camp Mae, a Scandinavian inspired A-Frame stay in Monteagle, TN. Minimalist designed yet elegant, offering the perfect escape- minutes from the Fiery Gizzard hiking trail and Monteagle. Relax in the hot tub or gather around the fire pit. For eco-conscious travelers, we provide an electric car charger. Experience seclusion of the mountains while only minutes from world class hiking, local restaurants and shops. This retreat harmonizes luxury with nature in a serene setting.

Indoor spacesFamilyTV

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.

4.99 out of 5 average rating, 238 reviews

2BR Nature Getaway in Tiny Home w/ Lake access

Nature's Nook is a charming two-bedroom cottage. Combining nature with cutting-edge design draws inspiration from all over. Providing a fairytale experience with a cozy interior amidst towering trees. Nature's Nook embraces the beauty of nature with the inside scent of a campfire-lit night to birds singing good morning. This provides the ideal getaway to relax but still includes hiking and adventure. Nature is calling you at the Nook. . . Follow us on our socials @NaturesNookTN

Indoor spacesFamilySleep quality

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.

Indoor spacesKitchenRiver

Superhost

Cabin in Winchester

4.82 out of 5 average rating, 164 reviews

VACATION CABIN - Sunday Morning Rentals

We are in Winchester, TN, and are located within a SHORT 5 MINUTE WALKING DISTANCE to Tims Ford Lake and Devil Step Boat Launch. Sunday Mornings Rentals is a completely equipped cabin that ensures a relaxing getaway. Perfect for all of your boating, fishing, and hiking recreations. The charming town square is approximately 5 miles from the rental - offering unique shops, a quaint theatre, and restaurants that are sure to provide enjoyment for everyone. PETS NOT ALLOWED.

KitchenIndoor spacesBackyard

4.98 out of 5 average rating, 381 reviews

Cabin in Coalmont

The Coalmont Cabin - Romantic Lakefront Escape

A quiet lakeside retreat made for slow mornings and star-filled nights. Wake to coffee on the deck as the fog drifts across the water, geese gather along the shoreline, and the world feels still for just a little longer. Spend your afternoons out on the lake, gliding through lily pads in a moment that feels like a scene from The Notebook. Tucked among the trees with a saltwater spa beneath the stars, The Cabin is where peaceful seclusion meets unforgettable memories.

KitchenIndoor spacesCheck-in

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!

KitchenIndoor spacesBathroom

Superhost

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

4.85 out of 5 average rating, 693 reviews

Scandinavian Treetop Bliss @ Terralodge

Soar into our Scandinavian treehouse on Monteagle’s "bio-gem"! Luxuriate in king beds, a hot tub, and smokeless firepit. Swim or fish in the shared pond, hike to our cave, or play lawn games. With fiber WiFi, 4K TV, and full kitchen, it’s perfect for work or play. Near Monteagle (7 min), Sewanee (15), The Caverns (25), plus epic hikes and lakes. Chattanooga (45 min), Nashville (90). Book this luxe treetop escape!

Indoor spacesFamilyQuiet

Popular amenities for Winchester family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 147 reviews

A modern cabin is shown with a sleek design, featuring a covered porch with a rail and stone base. Large windows allow natural light to enter, surrounded by trees in autumn colors. A grassy area is visible in the foreground.

Home in Tracy City

Cozy Two Bedroom Cabin with Hot Tub in Waters Edge

FamilyKitchenDecor

4.97 out of 5 average rating, 268 reviews

A treehouse structure is seen illuminated in the evening, showcasing a welcoming ambiance. A black calf stands in the grass near a fenced area, with the surrounding farm landscape and trees forming a serene backdrop.

Farm stay in Morrison

Phelps Pharm, I Was Almost A Treehouse

KitchenFamilyHiking

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.

4.99 out of 5 average rating, 100 reviews

Tiny Home in the Mountains w/firepit and Hot Tub

Indoor spacesKitchenComfort

A welcoming sign displays "The Fallen Acorn" beside the gravel driveway. The modern house features a combination of dark siding and natural stone elements, surrounded by a well-maintained landscape with rocks and trees. A distant view of the water is visible, enhancing the serene setting.

4.91 out of 5 average rating, 101 reviews

Quaint lakeside escape w/ hot tub & fire pit

FamilyKitchenCondition

4.96 out of 5 average rating, 194 reviews

Home in Tracy City

3-BR Luxury Home with Hot Tub & Arcade Games

Indoor spacesKitchenNearby

4.87 out of 5 average rating, 188 reviews

An outdoor gathering space is shown with a fire pit surrounded by stone seating. A cozy tiny home is visible in the background, adorned with warm string lights. Additional seating with Adirondack chairs is positioned nearby, contributing to a welcoming atmosphere.

Tiny home in Monteagle

Mac's Lodge Tiny Home

Indoor spacesFamilyLocation

4.89 out of 5 average rating, 492 reviews

A rustic log cabin is set within a spacious green yard, surrounded by trees. A gravel path leads to the entrance, with stairs ascending to the front porch. Windows provide views of the natural landscape, reflecting a serene outdoor environment.

Home in South Pittsburg

Martin Springs Cabin.

KitchenIndoor spacesQuiet

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.

4.94 out of 5 average rating, 244 reviews

Where Tiny Living Meets Big Lake Escapes

Indoor spacesKitchenParks

Family- and pet-friendly home rentals

5 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

Indoor spacesFamilyHospitality

4.92 out of 5 average rating, 132 reviews

Cabin in Sequatchie

Fireside Cabin on the Bluff

KitchenFamilyView

4.98 out of 5 average rating, 124 reviews

Home in Tracy City

Little Green Cottage

KitchenIndoor spacesNearby

4.94 out of 5 average rating, 216 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

Indoor spacesKitchenHot tub

4.96 out of 5 average rating, 222 reviews

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.

Home in Lynchburg

TN Fire 3 bedroom 2 bath beautiful new home

KitchenFamilyAir conditioning

4.93 out of 5 average rating, 141 reviews

A cozy bedroom features a spacious bed with soft, patterned bedding. Above the bed, a framed artwork adds a touch of color. A closet with neatly arranged shelves and a blue dresser is visible, providing ample storage. Soft lighting enhances the room's atmosphere.

Home in Sewanee

Relax & Unwind in Cozy Farm Stay 7 mins from I-24

FamilyIndoor spacesWalkability

4.89 out of 5 average rating, 312 reviews

A charming cottage is nestled among tall trees in a wooded area. The building features large windows that invite natural light, while a gravel pathway leads to the entrance. Dense greenery surrounds the cottage, creating a tranquil atmosphere.

Tiny home in Monteagle

The Nest at The Retreat @ Deer Lick Falls

Indoor spacesKitchenHiking

4.94 out of 5 average rating, 293 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

FamilyIndoor spacesGrill

Family-friendly home rentals with a pool

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, 60 reviews

Lakefront Haven | Hot Tub | Kayaks, Firepit

KitchenIndoor spacesValue

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

Indoor spacesKitchenBathroom

4.93 out of 5 average rating, 128 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

Indoor spacesKitchenCondition

4.94 out of 5 average rating, 71 reviews

Basecamp Retreat TimsFordLake

FamilyKitchenPool

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, 26 reviews

Barefoot Dreams

Indoor spacesKitchenLocation

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, 49 reviews

The Modern Mainstay at Barefoot Bay

Indoor spacesFamilyCleanliness

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!

FamilyIndoor spacesCondition

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.