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Family-friendly vacation rentals in Winchester

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Quick stats about vacation rentals that are family-friendly in Winchester

  • Total vacation rentals

    Explore 130 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at G$2,092 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,160 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Winchester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winchester rentals

  • 4.9 Average rating

    Winchester stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Winchester

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite
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)

4.86 out of 5 average rating, 212 reviews
Top guest favorite
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.
Home in Winchester

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

4.98 out of 5 average rating, 62 reviews
Guest favorite
A modern tiny home is surrounded by open grass fields, featuring a welcoming porch with wooden steps. Large windows provide natural light, while the exterior showcases a black siding and a gable roof. A gravel path leads to the entrance, enhancing accessibility.
Tiny home in Winchester

Tiny House

You will feel right at home in this adorable Tiny Home with RV Hookups! This picture-perfect little cottage has a bedroom with queen size bed, full bath with tile walk-in shower, full kitchen with all of the amenities, and living room with queen size sleeper sofa. The back porch offers peace, quiet, and spectacular mountain views. This property is super convenient to Tims Ford Lake, The Caverns music venue, Jack Daniels Distillery, University of the South, and historic downtown Winchester.

4.95 out of 5 average rating, 87 reviews
Top guest favorite
Home in Winchester

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

5.0 out of 5 average rating, 68 reviews
Top guest favorite
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.
Home in Winchester

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.

4.94 out of 5 average rating, 120 reviews
Top guest favorite
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.
Home in Winchester

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.

5.0 out of 5 average rating, 41 reviews
Top guest favorite
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.
Home in Winchester

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!

4.98 out of 5 average rating, 87 reviews
Guest favorite
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.
Home in Winchester

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 :)

4.98 out of 5 average rating, 122 reviews
Guest favorite
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.
Home in Winchester

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.

4.89 out of 5 average rating, 133 reviews
Top guest favorite
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.
Home in Winchester

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.

5.0 out of 5 average rating, 26 reviews
Guest favorite
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.
Apartment 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.

4.97 out of 5 average rating, 39 reviews
Top guest favorite
Home in Winchester

Water's Edge - Lakeside retreat

Experience spring by the water at this beautiful lakefront retreat designed for relaxing family getaways and group stays. The home features a private dock, spacious outdoor entertaining areas, panoramic lake views, and a hot tub perfect for unwinding after days spent outdoors. Gather around the outdoor gas fire pit in the evenings or enjoy meals together in the spacious dining areas inside. A peaceful and comfortable home base for enjoying the beauty of the season.

5.0 out of 5 average rating, 12 reviews

Popular amenities for Winchester family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
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

4.97 out of 5 average rating, 178 reviews
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

Scandinavian Treetop Bliss @ Terralodge

4.85 out of 5 average rating, 704 reviews
Top guest favorite
Cabin in Coalmont

The Coalmont Cabin - Romantic Lakefront Escape

4.98 out of 5 average rating, 384 reviews
Guest favorite
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!

4.89 out of 5 average rating, 255 reviews
Top guest favorite
A hot tub is positioned among trees, offering a view of the lake and surrounding nature. The clear blue water of the hot tub reflects sunlight, while a wooden pathway leads to the water's edge in the background. The serene atmosphere is enhanced by green foliage.
Home in Tracy City

Lakefront w/ Hot Tub + Kayaks + Fire Pit

5.0 out of 5 average rating, 106 reviews
Top guest favorite
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

4.97 out of 5 average rating, 271 reviews
Top guest favorite
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 in the Mountains w/firepit and Hot Tub

4.99 out of 5 average rating, 103 reviews
Top guest favorite
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.
Tiny home in Tracy City

Spacious Lakeside Retreat w/ Hot Tub & King Beds

4.99 out of 5 average rating, 144 reviews

Family- and pet-friendly home rentals

Top guest favorite
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

5.0 out of 5 average rating, 109 reviews
Top guest favorite
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.
Cabin in Lynchburg, Moore County

Cozy Cabin on Tims Ford Lake

4.97 out of 5 average rating, 235 reviews
Top guest favorite
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

4.94 out of 5 average rating, 294 reviews
Guest favorite
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

4.98 out of 5 average rating, 241 reviews
Top guest favorite
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

4.95 out of 5 average rating, 221 reviews
Top guest favorite
A charming cabin with a green metal roof is situated on a grassy hillside. Surrounding trees frame the view, while steps lead from the driveway to the entrance. The cabin overlooks the valley, providing a scenic backdrop of rolling hills in the distance.
Cabin in Altamont

Sunrise Mountain Cabin

4.97 out of 5 average rating, 630 reviews
Top guest favorite
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.
Guesthouse in Lynchburg, Moore County

Country Guest House

4.96 out of 5 average rating, 325 reviews
Top guest favorite
Tiny home in Tracy City

Nature lovers dream retreat/the Square Root

4.99 out of 5 average rating, 112 reviews

Family-friendly home rentals with a pool

Top guest favorite
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

5.0 out of 5 average rating, 106 reviews
Top guest favorite
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

4.93 out of 5 average rating, 131 reviews
Top guest favorite
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

4.99 out of 5 average rating, 104 reviews
Guest favorite
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.
Home in Winchester

Luxurious New Build LakeHouse Tim’s Ford 4BR4Bath

4.92 out of 5 average rating, 48 reviews
Top guest favorite
Home in Winchester

Tennessee Pearl: lakefront-amazing views-lake toys

5.0 out of 5 average rating, 26 reviews
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.
Home in Winchester

Lakeside Luxe | Lake + Pool Access

4.79 out of 5 average rating, 28 reviews
Guest favorite
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.
Home in Winchester

The Perfect Getaway

4.92 out of 5 average rating, 13 reviews
Top guest favorite
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.
Home in Winchester

The Modern Mainstay at Barefoot Bay

5.0 out of 5 average rating, 49 reviews

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$37,238 GYDG$33,891 GYDG$40,376 GYDG$47,280 GYDG$56,276 GYDG$68,828 GYDG$65,272 GYDG$60,669 GYDG$45,606 GYDG$47,280 GYDG$47,699 GYDG$39,121 GYD
Avg. temp5°C8°C12°C17°C21°C25°C27°C27°C23°C17°C11°C7°C

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