
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.

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

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

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

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

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

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

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

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

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

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

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

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
Family-friendly home rentals with a hot tub

Modern Monteagle A-frame with Hot Tub
KitchenIndoor spacesWifi

Lakefront w/ Hot Tub, Kayaks, & Firepit
KitchenFamilyComfort

Tiny Home in the Mountains w/firepit and Hot Tub
Indoor spacesFamilyLaundry

Fire Lake Lodge Volleyball, Hot Tub, Kayaks!
KitchenIndoor spacesHot tub

3-BR Luxury Home with Hot Tub & Arcade Games
FamilyIndoor spacesHospitality

Mac's Lodge Tiny Home
Indoor spacesFamilyCheck-in

Cliffside Treehouse Loft | Epic Views
KitchenFamilyHospitality

Where Tiny Living Meets Big Lake Escapes
FamilyKitchenHot tub
Family- and pet-friendly home rentals

Lakeside Retreat at The Reserve w/ Golf Cart
FamilyIndoor spacesLaundry

Cozy Cabin close to Tims Ford Lake & Jack Daniels
KitchenIndoor spacesCondition

Holliday Hide Away
KitchenIndoor spacesLong stay

Nature lovers dream retreat/the Square Root
KitchenFamilyCheck-in

Sunrise Mountain Cabin
FamilyKitchenDecor

Little Green Cottage
Indoor spacesFamilyValue

The Nest at The Retreat @ Deer Lick Falls
KitchenIndoor spacesPets

Phelps Pharm, I Was Almost A Treehouse
Indoor spacesKitchenLocation
Family-friendly home rentals with a pool

Beautiful Tim's Ford Lake House (Sleeps 20)
KitchenFamilyHiking

Private Treehouse Retreat! Sauna|Hot Tub|Pool
FamilyKitchenHospitality

Cozy Cabin in the Clouds
FamilyIndoor spacesPool

Barefoot Dreams
FamilyKitchenBiking

The Modern Mainstay at Barefoot Bay
FamilyKitchenBathroom

Lakefront Haven | Hot Tub | Kayaks, Firepit
FamilyKitchenGrill

Luxurious New Build LakeHouse Tim’s Ford 4BR4Bath
KitchenFamilyAir conditioning

Basecamp Retreat TimsFordLake
KitchenIndoor spacesPool
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 654 | ﺩ.ﺇ 595 | ﺩ.ﺇ 709 | ﺩ.ﺇ 830 | ﺩ.ﺇ 988 | ﺩ.ﺇ 1,208 | ﺩ.ﺇ 1,146 | ﺩ.ﺇ 1,065 | ﺩ.ﺇ 801 | ﺩ.ﺇ 830 | ﺩ.ﺇ 837 | ﺩ.ﺇ 687 |
| Avg. temp | 5°C | 8°C | 12°C | 17°C | 21°C | 25°C | 27°C | 27°C | 23°C | 17°C | 11°C | 7°C |
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- Hunter Museum of American Art
- Von Braun Center, North Hall
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- Henry Horton State Park





