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)

FamilyKitchenComfort

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.

KitchenIndoor spacesBathroom

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

Indoor spacesFamilyAccess

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 spacesKitchenHospitality

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!

Indoor spacesFamilyLaundry

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 spacesKitchenQuiet

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

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.

FamilyIndoor spacesPets

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.

Indoor spacesKitchenValue

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.

Indoor spacesKitchenNearby

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!

FamilyIndoor spacesCondition

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, 692 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 spacesFamilyDecor

4.99 out of 5 average rating, 109 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."

Indoor spacesFamilyView

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

Indoor spacesFamilyComfort

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

FamilyIndoor spacesHiking

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, 100 reviews

Quaint lakeside escape w/ hot tub & fire pit

Indoor spacesFamilyComfort

4.96 out of 5 average rating, 194 reviews

Home in Tracy City

3-BR Luxury Home with Hot Tub & Arcade Games

KitchenFamilyLaundry

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

FamilyKitchenLaundry

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

FamilyIndoor spacesBackyard

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.

FamilyIndoor spacesView

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

KitchenIndoor spacesCheck-in

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

KitchenFamilyNearby

4.92 out of 5 average rating, 132 reviews

Cabin in Sequatchie

Fireside Cabin on the Bluff

FamilyIndoor spacesDecor

4.97 out of 5 average rating, 267 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

KitchenIndoor spacesParks

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

KitchenIndoor spacesNearby

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

FamilyKitchenCheckout

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

Indoor spacesFamilyAccuracy

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

KitchenFamilyAccess

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

FamilyKitchenLocation

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

Indoor spacesKitchenDecor

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 spacesFamilyAccuracy

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

FamilyKitchenAccuracy

4.94 out of 5 average rating, 71 reviews

Basecamp Retreat TimsFordLake

FamilyIndoor spacesComfort

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 spacesFamilyView

4.89 out of 5 average rating, 27 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

KitchenIndoor spacesOutdoor spaces

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 spacesAccess

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.