Family-friendly holiday rentals in Winchester

The exterior of the cabin is displayed, featuring a blend of stone and modern siding. Surrounding trees are visible, with a clear path leading up to the entrance. A detached garage can be seen to the left of the cabin, set among the natural landscape.

4.99 out of 5 average rating, 118 reviews

Spacious Lakeside Retreat w/ Hot Tub & King Beds

Take it easy at this unique and tranquil getaway home. Our custom built tiny cabin has 744 sq ft of indoor living with two private bedrooms and 2 full baths. The loft is great for kids. Additional amenities include fireplace, dedicated working space and fully stocked kitchen. Outdoor area includes a large deck, fire pit, luxury hot tub and grill. Sits on 2 acres of wooded land & features a community lake down the street. If you have additional guests, ask about our tree house located next door.

4.89 out of 5 average rating, 474 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.

This country cabin is a great base for exploring the nearby South Cumberland Park and surrounding area. Convenient to Sweetons Cove Gulf, The Caverns, Adventure Offroad Park, Sewanee, Monteagle, South Pittsburg/Cornbread Festival, Jasper Highlands. right next to I-24. You can't see any other homes from the cabin and adjacent meadow. Year round creek in the property. Meadow trail. New Hot Tub and all new Tuft & Needle mattresses for 2022! Basic amenities provided. Includes Wi-Fi and DVD player.

4.94 out of 5 average rating, 210 reviews

The exterior of the property features a unique sloped roof with a combination of stone and wood materials. Surrounded by greenery, the entrance is approached via a paved path that leads to a welcoming entrance area. Outdoor seating is visible on the balcony, nestled among the trees.

Home in Manchester

Chalet 638 - state park, golf & The Caverns

Short walk to a state park with golfing. This first floor living space has a kitchen, walk-in closet, large wood fireplace, workout equipment, washer/dryer, grill, fire pit and lots of space. Old Stone Fort Archeological Park with multiple hiking trails, fishing, canoeing and a $9 a round golf course are seconds away. Close to I-24 this centrally located Tennessee property gives equal access from Nashville to Chattanooga. Explore parks, vineyards, distilleries and Tennessee history from here.

4.95 out of 5 average rating, 279 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

1200 sq. ft. very rustic converted pole barn. The floors are stained concrete and the walls are rough saw mill hewn poplar boards. Located on 3 acres of beautiful well kept property. It does not border the lake but is surrounded by Tims Ford Lake and less than 5 minute drive to 3 boat docks and launches. Close to restaurants, shopping venues, hiking trails, water falls and golfing. Pool table, cornhole set, board games & cards in cabin. Visit historic Franklin County and surrounding areas.

4.9 out of 5 average rating, 294 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

The Retreat offers a cozy cottage for down time & you have the option to hike trails down to falls area, socialize with other guests or sit and have your own Fire in our fire pit on the property and just relax! Local Restaurants minutes away, lake access 10 minutes away with beautiful woodsy setting perfect for getting away from the hustle of everyday life! Covered patio for relaxing and you can eat outdoors with a grill guests can use and a fully equipped kitchen if you choose to cook.

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, 102 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 :)

4.96 out of 5 average rating, 127 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.

5 out of 5 average rating, 103 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 light-filled living area is depicted, featuring a spacious white sofa, a wooden coffee table, and a modern entertainment unit with a large screen. Two hanging chairs are visible, accompanied by a lush greenery plant. Large windows provide views of the surrounding trees.

4.98 out of 5 average rating, 158 reviews

the tiny bungalow @ waters edge | tiny house

welcome to our favorite little bungalow. located in tracy city, tn @ the waters edge tiny house community. cozied in the woods, we love to host our guest not just with a retreat but an experience. we have deigned our place to have what you need, so you can show up and rest. our tiny bungalow is perfectly designed for that romantic getaway, a writers retreat, an escape for friends to connect over an open fire, or a family adventure hiking the trails + paddling out on the 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, 124 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.

Superhost

A charming farmhouse is set against a backdrop of open green space, featuring a covered front porch and large windows that provide natural light. The exterior is highlighted by a green metal roof and white siding, creating a welcoming presence in a serene rural setting.

4.82 out of 5 average rating, 136 reviews

Spacious 4BR/3BA Home Near Tims Ford Lake

Welcome to your beautifully renovated 1940s 4-bedroom, 3-bathroom vacation home near Tims Ford Lake! This spacious historic retreat comfortably sleeps 8 and offers everything you need for a relaxing getaway in Winchester, TN. Enjoy fast Wi-Fi, a Roku Smart TV, and a large private yard perfect for watching the sunrise from the back porch and sunset from the front. Large bedrooms, a cozy reading nook, and a spacious kitchen and living area awaits you!

Campervan/Motorhome in Sewanee

A vintage Airstream is nestled among lush greenery, highlighted by hanging flower baskets and potted plants. A wooden deck with a welcome mat provides outdoor seating, creating a cozy atmosphere for relaxation. Ambient lighting adds to the inviting setting.

4.93 out of 5 average rating, 212 reviews

Airstream #97 at The Grove

Sleep in a vintage 1997 Airstream! Fully updated with modern comforts, #97 is nestled in our forest campground, the perfect spot for your laid back Mountain getaway. The Grove at Natural Bridge features 3 vintage Airstreams, a shared well appointed bathhouse and restrooms. Located just a short drive (2.2 miles) from The University of the South and walking distance to Natural Bridge State Park.

Popular amenities for Winchester family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 152 reviews

The tiny home sits nestled by the waterfront, surrounded by trees. A large deck features two lounge chairs and a hot tub, with string lights illuminating the area. A fire pit and seating are positioned near the water, enhancing the serene outdoor environment.

Tiny home in Coalmont

The Coalmont Cove - Romantic Lakefront Escape

4.92 out of 5 average rating, 119 reviews

A rustic log cabin is set amidst trees, featuring a spacious front porch with wooden railings and outdoor seating. Stone accents complement the structure, which is partially surrounded by lush greenery. The cabin's design merges natural beauty with comfortable outdoor living space.

Cabin in Tullahoma

Private lakefront log cabin w/dock & hot tub

4.96 out of 5 average rating, 250 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

4.85 out of 5 average rating, 627 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

4.96 out of 5 average rating, 102 reviews

Cabin in Monteagle

Cozy Bluff View Cabin w/ Hot tub in Monteagle

4.86 out of 5 average rating, 148 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

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, 226 reviews

Proof That Less Really Is More.

5 out of 5 average rating, 184 reviews

A cozy sleeping area is shown with a spacious bed covered by a textured blanket. The elevated tent features open mesh windows, offering unobstructed views of the landscape beyond, with natural light illuminating the wooden walls and nearby bedside lamp.

Tent in Altamont

Luxury Safari Tent | 15 Mins to Top TN Waterfall

Family- and pet-friendly home rentals

5 out of 5 average rating, 235 reviews

A single-story house is depicted, featuring a welcoming front porch with a ramp for accessibility. Lush greenery surrounds the home, with flowering shrubs adding color. Large windows are framed by burgundy shutters, and the backdrop reveals rolling hills under a clear blue sky.

Cottage in Whitwell

Granny's Guest House

4.93 out of 5 average rating, 102 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

4.92 out of 5 average rating, 133 reviews

A charming cottage built with light-colored stone is framed by lush green shrubs and blooming hydrangeas. The entrance features a covered archway, with windows on either side allowing natural light to enter. A well-maintained pathway leads to the front door.

Home in Lynchburg

Mulberry Cottage Guest House

4.94 out of 5 average rating, 193 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

The exterior of the tiny home is surrounded by trees and features large windows that allow for natural light. A covered porch with seating provides a welcoming entryway, while a firepit area is visible, surrounded by lush greenery and stone pathways.

4.95 out of 5 average rating, 244 reviews

The Water & Woods Tiny Home Water's Edge

4.9 out of 5 average rating, 194 reviews

A spacious living area features large windows that let in natural light and provide views of the surrounding trees. A comfortable dark leather sofa is arranged with a rustic wooden coffee table. A wooden rocking chair adds to the cozy atmosphere, beside a staircase made of light-colored wood.

Home in Sewanee

Return Guest House and Writers’ Retreat

4.92 out of 5 average rating, 132 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

4.98 out of 5 average rating, 638 reviews

Farm stay in Dunlap

Come Stay & Play at the farm

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, 46 reviews

Lakefront Haven–Hot Tub & Heated Porch

Superhost

A serene view of a meandering lake is surrounded by lush greenery and wooded banks. The water reflects the blue sky and scattered white clouds, creating a calm and peaceful landscape. The vibrant colors of nature are prominently displayed in this tranquil setting.

5 out of 5 average rating, 15 reviews

Luxurious Lakefront! Marina, Fire Pit, Location!

Superhost

Cabin in Bryant

4.83 out of 5 average rating, 115 reviews

Eagles Nest Cabin – Bluff Views & Hot Tub!

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

A modern house with a striking dark exterior stands against a colorful sunset. The façade features large windows framed by light trim, with a prominent gabled entrance. The surrounding yard is well-maintained, and a glimpse of the lake is visible in the background.

4.93 out of 5 average rating, 61 reviews

Basecamp Retreat TimsFordLake

4.87 out of 5 average rating, 61 reviews

Cabin in Jasper

Chic 2BR Cabin D by MHM Luxury Properties

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, 37 reviews

The Modern Mainstay at Barefoot Bay

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.