
Family-friendly vacation rentals in Winchester
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Winchester
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.

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.

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.

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.

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.

Cozy tiny home ☆Sleeps 4 w/ great outdoor space
Relax & unwind at our tiny home located in Tracy City Sleeps 4-Queen bed in private bedroom & upstairs loft Covered deck w/ gas firepit Campfire in backyard Electric fireplace inside Outdoor obstacle course for kids Fully stocked kitchen 3 Tv's, DVD players & DVD's Fishing poles Great restaurants and shops Bike and hiking trails nearby Kayak & canoe rentals Gas grill 90 min from Nashville, 45 min from Chattanooga, & 15 min from the University of the South in Sewanee.

The Milk Barn Cottage
Built in the late 1940's as a working milk barn, the Milk Barn Cottage is 800 sq. ft of cozy comfort. The cottage is near the foot of Monteagle Mountain in the beautiful Pelham Valley. We are half-way between Nashville and Chattanooga, about 2 miles off exit 127 on I-24. The Caverns is about an 8 minute drive away. Pelham has quaint restaurants to visit plus all of the natural beauty in our area. We are also just 13 miles from Sewanee and the University of the South.

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.

The Barn @ Dreamcatcher Farm
Make sure to “heart” our listing so you can find us when you are ready to book. Live the farming dream in Middle Tennessee on Dreamcatcher Farm. Our 13 acre farm is home to Nigerian Dwarf goats, Santa Gerturdus cattle, a couple of horses, and the Labs and barn cats that run the operation. Come enjoy some down time in a quiet country setting with friendly farm animals.

Phelps Pharm Bunkhouse
Farm bunkhouse with stall boarding availability for our guests with horses. Our bunkhouse and location is great for individuals/couples and can accommodate a family of 4. Please visit our website at Phelpspharm.farm for more information, our story and pictures. There is a link on the website that will take you back to AirBnB to continue your reservation. Thank You.

Creekside at Rutledge Falls
Cozy nest right on the creek. Lots of privacy. Hiking trails and Waterfalls nearby. Listen to the water from a porch swing overlooking the creek. We have a double recliner for movies and popcorn. This efficiency apartment has a private entrance with private covered porch and a full kitchen. Work area with Wi-Fi. Pets are welcome - must be free of fleas and ticks.

The Wright Place Apartment
Precious, cozy efficiency apartment with a queen size Serta mattress and a full size 8” foam loft bed. Full kitchen with large bar for eating. All dishes and pots and pans supplied. Nice big shower. Private entrance with pergola, grill and fire pit. One hour from Chattanooga and one hour from Nashville, with hiking and nature sites within 20-30 minutes.
Popular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

Private lakefront log cabin w/dock & hot tub

Cozy Two Bedroom Cabin with Hot Tub in Waters Edge

Sweet Dee's Tiny Home

Our Catty Shack

Tennessee’s Only Luxury Safari Tent Getaway

3-BR Luxury Home with Hot Tub & Arcade Games

Still Waters Tiny Home: Waterfront/Kayaks/HotTub

Modern Monteagle A-frame with Hot Tub
Family- and pet-friendly home rentals

Mulberry Cottage Guest House

Sunrise Mountain Tree House Cabin

Nature’s Tiny Riverside Hideaway

Country Cottage Hideaway near Lynchburg

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

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

Secluded Country Cabin between city and country

Moonshine Runners Cabin
Family-friendly home rentals with a pool

Lakefront Haven–Fall Escape w/ Firepits + Kayak

Monteagle/Sewanee forest cottage with amenities

Heaven’s View Lodge, Pool, Pet Friendly

Stunning Lakefront! Pool, Kayaks, Bikes, Marina!

Cloud 9 Cabin with an indoor pool, hot tub, & fire

Fall Vibes- Spa & Fire Place | Mins to Chattanooga

Whiskey River Retreat-The Barn with minis

Lovely Lake View Home at Twin Creeks Marina
Quick stats about vacation rentals that are family-friendly in Winchester
Total rentals
120 properties
Nightly prices starting at
€ 43 before taxes and fees
Total number of reviews
3.5K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Destinations to explore
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- Cabin rentals Winchester
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- Rentals with a kayak Winchester
- Rentals with a patio Winchester
- Pet-friendly rentals Winchester
- Rentals with a fireplace Winchester
- Rentals with lake access Winchester
- Rentals with a fire pit Winchester
- Rentals with pools Winchester
- Rentals with a washer and dryer Winchester
- Rentals with outdoor seating Winchester
- Family-friendly rentals Franklin County
- Family-friendly rentals Tennessee
- Family-friendly rentals United States
- Cloudland Canyon State Park
- Tennessee Aquarium
- Monte Sano State Park
- Sweetens Cove Golf Club
- Black Creek Club
- Coolidge Park
- The Ledges
- Chattanooga Golf and Country Club
- Chattanooga Choo Choo
- The Lookout Mountain Club
- Old Fort Golf Course
- Hunter Museum of American Art
- Creative Discovery Museum
- National Medal of Honor Heritage Center