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.

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Guest favorite
A rustic log cabin is set within a spacious green yard, surrounded by trees. A gravel path leads to the entrance, with stairs ascending to the front porch. Windows provide views of the natural landscape, reflecting a serene outdoor environment.
Home in South Pittsburg
4.9 out of 5 average rating, 467 reviews

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.

Top guest favorite
The exterior of the property features a unique sloped roof with a combination of stone and wood materials. Surrounded by greenery, the entrance is approached via a paved path that leads to a welcoming entrance area. Outdoor seating is visible on the balcony, nestled among the trees.
Home in Manchester
4.93 out of 5 average rating, 190 reviews

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.

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
4.95 out of 5 average rating, 277 reviews

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.

Guest favorite
A charming cottage is nestled among tall trees in a wooded area. The building features large windows that invite natural light, while a gravel pathway leads to the entrance. Dense greenery surrounds the cottage, creating a tranquil atmosphere.
Tiny home in Monteagle
4.9 out of 5 average rating, 284 reviews

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.

Guest favorite
A light-filled living area is depicted, featuring a spacious white sofa, a wooden coffee table, and a modern entertainment unit with a large screen. Two hanging chairs are visible, accompanied by a lush greenery plant. Large windows provide views of the surrounding trees.
Tiny home in Tracy City
4.98 out of 5 average rating, 148 reviews

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.

Top guest favorite
The interior showcases high ceilings with a large clock prominently displayed above a comfortable seating area. Natural light filters through multiple windows, highlighting a cozy living space that opens onto a covered deck featuring a circular seating arrangement around a firepit.
Tiny home in Tracy City
4.99 out of 5 average rating, 287 reviews

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.

Top guest favorite
The cottage exterior displays a charming entrance with a light blue door framed by a wreath. A cozy seating area is present with two chairs and a small table. A wooden fence adds privacy, and flowering plants are planted along the stone pathway.
Cottage in Village of Pelham
5 out of 5 average rating, 503 reviews

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.

Top guest favorite
A vintage Airstream is nestled among lush greenery, highlighted by hanging flower baskets and potted plants. A wooden deck with a welcome mat provides outdoor seating, creating a cozy atmosphere for relaxation. Ambient lighting adds to the inviting setting.
Camper/RV in Sewanee
4.94 out of 5 average rating, 205 reviews

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.

Top guest favorite
A rustic barn is shown beside a wooden fenced area, with a large open field visible in the background. The scene is framed by a tree with green leaves, and a decorative sun motif is positioned on the barn's exterior.
Barn in Tullahoma
4.98 out of 5 average rating, 195 reviews

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.

Guest favorite
The image captures a serene landscape at sunrise, featuring soft hues of orange and yellow illuminating the sky. Silhouettes of trees line the horizon, while the gentle rise of distant hills is visible against the morning light.
Farm stay in Morrison
4.96 out of 5 average rating, 324 reviews

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.

Top guest favorite
A serene view of a creek surrounded by lush greenery and trees. Wooden steps lead down to the water's edge, creating a natural pathway. The creek's flowing water reflects the surrounding foliage, enhancing the tranquil setting.
Guest suite in Manchester
4.98 out of 5 average rating, 419 reviews

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.

Guest favorite
An outdoor patio area is framed by a wooden pergola, providing shade. A small grill is positioned nearby, alongside two black wrought-iron chairs at a circular table. Light streams through the pergola's slats, highlighting the concrete floor.
Apartment in Hillsboro
4.95 out of 5 average rating, 271 reviews

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

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