
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 G$2,083 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.

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)

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

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.

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!

1940 Renovated Cottage Near Square/Lake Summer Fun
WELCOME to this beautiful, newly renovated COTTAGE near the Winchester Square and Tim's Ford Lake. This Historic Home, built in 1948 is full of CHARACTER but yet modern and stylishly furnished. Within walking distance to the Winchester Square and just 1 mile from Twin Creeks Marina this beautiful home is convenient, comfortable, and welcoming for all guests. This is the home that you have been looking for that is BUDGET friendly but also packed with AMENITIES in the perfect location!

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.

2BR Nature Getaway in Tiny Home w/ Lake access
Nature's Nook is a charming two-bedroom cottage. Combining nature with cutting-edge design draws inspiration from all over. Providing a fairytale experience with a cozy interior amidst towering trees. Nature's Nook embraces the beauty of nature with the inside scent of a campfire-lit night to birds singing good morning. This provides the ideal getaway to relax but still includes hiking and adventure. Nature is calling you at the Nook. . . Follow us on our socials @NaturesNookTN

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.

Cozy Cabin close to Tims Ford Lake & Jack Daniels
A cozy cabin awaits you located close to Tim's Ford Lake-1/2 mile from Holiday Landing Marina & Blue Gill Restaurant. Lynchburg, home to popular Jack Daniel's Distillery-only 12 miles away; Nashville-90 mins. Made from handcrafted red cedar, you will be met with a woodsy aroma when entering. Special touches can be found throughout including Jacuzzi tub! Truly a unique wooded cottage, equipped to ensure a relaxing getaway. Pet friendly with an additional pet fee.

"Near Caverns and Sewanee 2-bedro/2-bath w/EV char
2 bedroom, 2 full bathrooms, totally remodeled home with a large fenced back yard and fully equipped modern kitchen. Easy drive less than 7-mi to Sewanee, and just 10-miles/ 10-12 min to The Caverns. The "Farm View" house offers country views with privacy. A serene place to relax, unwind and retreat while enjoying pastures and country views. "EV/Tesla wall charger", Starlink internet w/ streaming tv. Only 3.5 miles off 1-24 exit 127, Pelham, Winchester.

Lovely Lake View Home at Twin Creeks Marina
This Craftsman-style, lake-view house is located in the private, gated lakeside community of Twin Creeks Village at scenic Tim's Ford Lake in Winchester, TN. It features an open floor plan with 4 bedrooms, 3 baths, game room, screened porch and huge deck overlooking the lake. Use the included golf cart to go to the swimming pools, marina, bar & grill or on-site convenience store. Information on boat & jet ski rentals are available at the marina shop.

Basecamp Retreat TimsFordLake
Welcome to Basecamp Retreat! Modern lake luxury on Tims Ford Lake. This 3-bedroom, 2.5 bath cozy retreat, located in the gated community of Barefoot Bay, is the perfect home base for your visit. Offering modern comforts and convenience in a prime location with picturesque lake views, Basecamp provides a comfortable and inviting space to relax and recharge. Located 2 miles from Twin Creeks Marina & Resort and 1 mile from downtown Winchester.
Popular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

3-BR Luxury Home with Hot Tub & Arcade Games

Modern Treehouse Loft | Epic Views · Hot Tub

The Coalmont Cabin - Romantic Lakefront Escape

Still Waters Tiny Home: Waterfront/HotTub/Kayaks

Modern Monteagle A-frame with Hot Tub

Mac's Lodge Tiny Home

Martin Springs Cabin.

Cozy Tiny Home w/large deck, hot tub and firepit
Family- and pet-friendly home rentals

Lakeside Retreat at The Reserve w/ Golf Cart

Dock on Lake! Walk to Downtown Shops/Rest/Movies!

Relax & Unwind in Cozy Farm Stay 7 mins from I-24

Come Stay & Play at the farm

Cottage on Cedar

The Nest at The Retreat @ Deer Lick Falls

Nature lovers dream retreat/the Square Root

A quiet getaway.
Family-friendly home rentals with a pool

Luxury 3BR lakeside escape

Lakefront Haven | Hot Tub | Kayaks, Firepit

TC Easy Breeezee

Lakeside Luxe | Lake + Pool Access

Private lakefront log cabin w/dock & hot tub

The Old Fashioned w/ lake view & FREE pontoon!

Barefoot Dreams

The Modern Mainstay at Barefoot Bay
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$37,075 GYD | G$33,743 GYD | G$40,200 GYD | G$39,783 GYD | G$54,988 GYD | G$65,194 GYD | G$64,986 GYD | G$60,404 GYD | G$45,407 GYD | G$47,073 GYD | G$47,490 GYD | G$38,950 GYD |
| 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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- Rentals with a kayak Winchester
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- Rentals with pools Winchester
- Rentals with lake access Winchester
- Rentals with a fire pit Winchester
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- Pet-friendly rentals Winchester
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- Family-friendly rentals Franklin County
- Family-friendly rentals Tennessee
- Family-friendly rentals United States
- Cloudland Canyon State Park
- Tennessee Aquarium
- Monte Sano State Park
- Rock City
- Chattanooga Choo Choo
- Coolidge Park
- South Cumberland State Park
- Point Park
- Hunter Museum of American Art
- Von Braun Center, North Hall
- Raccoon Mountain Caverns & Campground
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- Old Stone Fort State Archaeological Park
- Creative Discovery Museum
- U.S. Space & Rocket Center
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- Lowe Mill Arts And Entertainment
- Cumberland Caverns
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- Short Mountain Distillery
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