Family-friendly vacation rentals in Winchester

Find and book unique family-friendly homes on Airbnb

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 ﺩ.ﺇ 37 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
4.86 out of 5 average rating, 211 reviews

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)

KitchenFamilyWifi

Top guest favorite
Home in Winchester
5.0 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 spacesKitchenParking

Guest favorite
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.
Home in Winchester
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!

KitchenFamilyParks

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
4.98 out of 5 average rating, 85 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!

FamilyKitchenPets

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
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 :)

FamilyKitchenView

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
4.97 out of 5 average rating, 234 reviews

Cozy Cabin on Tims Ford Lake

Come stay at a hand built log cabin nestled right on Tims Ford Lake. Enjoy a cup of coffee and watch birds fly in a rocking chair on the front porch. Relax in the porch swing as you see fish jump from the water. Grill out on the back porch while watching the sun set. There is a dock available for fishing. The cabin is five miles from Tims Ford State Park, eight miles from Jack Daniels Distillery and downtown Lynchburg, eleven miles from Tullahoma, and fifteen miles from Winchester.

FamilyKitchenOutdoor spaces

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
4.93 out of 5 average rating, 130 reviews

Private lakefront log cabin w/dock & hot tub

Be one with nature at this unique, tranquil getaway on Tim’s Ford Lake. Enjoy the two fireplaces in a “rustic” meets “modern” log cabin on 10 acres of privacy that is adjoined to over 2000 acres of park land. There is 450 ft of lake front & private dock to store your boat/toys, but the dock is not usable Nov 1 to April 1. Enjoy nature walks, spend lake time with friends or just relax taking in the amazingly beautiful views, hot tub and amenities. This truly is our happy place.

Indoor spacesFamilyHospitality

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
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.

KitchenIndoor spacesCheck-in

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.

FamilyIndoor spacesBeach

Top guest favorite
Cabin in Coalmont
4.98 out of 5 average rating, 381 reviews

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.

FamilyKitchenLocation

Guest favorite
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.
Home in Winchester
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!

Indoor spacesFamilyCleanliness

Top guest favorite
The A-frame exterior is surrounded by lush greenery, creating a serene environment. A gravel driveway leads to the entrance, with a porch featuring seating and a suspended swing. A small woodland area contains neatly stacked firewood and a bicycle, enhancing the rustic charm.
Tiny home in Tracy City
4.97 out of 5 average rating, 102 reviews

A-Frame Nature Getaway/Lake Access/Pet Friendly

Discover the enchanting Hiker's Hideaway, a cozy retreat nestled in nature. Blending modern design with natural elements, this hideaway offers a fairytale experience surrounded by majestic trees. Immerse yourself in the beauty of nature, from the scent of a crackling campfire to the melody of birds at dawn. Perfect for those seeking relaxation and adventure, Hiker's Hideaway beckons you to answer the call of the wild...

KitchenFamilyValue

Popular amenities for Winchester family-friendly rentals

When is the best time to visit Winchester?

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Avg. priceﺩ.ﺇ 654ﺩ.ﺇ 595ﺩ.ﺇ 709ﺩ.ﺇ 830ﺩ.ﺇ 988ﺩ.ﺇ 1,208ﺩ.ﺇ 1,146ﺩ.ﺇ 1,065ﺩ.ﺇ 801ﺩ.ﺇ 830ﺩ.ﺇ 837ﺩ.ﺇ 687
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