Kid-friendly vacation rentals in Winchester

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Winchester

Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.

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Guest favorite

A spacious cabin features a sloped roof and large windows, surrounded by lush greenery. An expansive wooden deck extends from the cabin, showcasing lounge furniture and planters. The serene forest setting complements the inviting outdoor space, perfect for relaxation and enjoying nature.

Cabin in Monteagle

4.93 out of 5 average rating, 167 reviews

Monteagle Mountain Serenity Nashville Chattanooga

"FAMILY CABIN" WITH VIEWS EVENTS OR LOUD PARTIES ARE NOT ALLOWED. NEAR MUSIC CITY USA AND CHATTANOOGA MILES HIKING TRAILS AND NINE NEARBY WATERFALLS After a day of exploring relax on the OVER SIZED Deck PANORAMIC MOUNTAIN VISTA'S GAS FIRE PLACE , FIRE PIT & GRILL FULLY STOCKED KITCHEN KING SUITE w/CUSTOM SHOWER QUEEN BEDROOM & 3 bed BUNK ROOM ADDITIONAL FULL CUSTOM BATH 4 TV's INTERNET & cable All the beauty of The SMOKEY'S without the crowds.

Top guest favorite

Cottage in Tullahoma

4.98 out of 5 average rating, 111 reviews

Cottage at The Reserve sleeps 10

Perfect family friendly get-away at Tims Ford Lake. The cottage is located on a beautiful, completely wooded lot. You have access to Holiday Landing Marina via a subdivision golf cart path. Whether you want to go boating on the lake, hike at the nearby Tims Ford State Park, or just get together with family and friends, look no further! This large open concept, cozy, spacious, 3-level home is all you will need. Brand new furnishings and mattresses! Our space also includes 5 large 4K ROKU TVs.

Top guest favorite

A cozy living area features a leather sectional sofa positioned on a soft area rug. Large sliding doors lead to a screened porch, allowing natural light to fill the space. Decorative lighting fixtures add a modern touch to the open floor plan connecting to the kitchen.

Home in Tullahoma

5 out of 5 average rating, 35 reviews

New Cottage on Tims Ford Lake/Marina/Restaurant

New, Beautiful Cottage /at Tims Ford Lake.Enjoy the private golf cart path/ parking by the water, marina, restaurant. Enjoy screen porch/front porch/fiber internet and tv in every bedroom/living room/and on screen porch.Bedroom down with King/Bedroom up with King/Bedroom up with 5 twin beds/2 full baths/1 powder bath down/Outside grill/ Washer and Dryer/Large Driveway/Boat slips to use. Boat rentals at Holiday Marina. Drafts and Watercrafts another restaurant by the water. No pets allowed

Guest favorite

A playground structure is nestled among trees with autumn leaves covering the ground. The design includes a green slide, climbing wall, and wooden platforms, offering a fun space for children to play in a natural setting.

Home in Tracy City

4.96 out of 5 average rating, 103 reviews

Cozy Two Bedroom Cabin with Hot Tub in Waters Edge

New 2 bedroom cabin in the Water's Edge community. Spacious family room to enjoy fireplace, TV, and dining area. Private hot tub! Master bedroom has a king sized bed. The second bedroom has 2 twin bunk beds, trundle, and a loft. Outdoor living space patio with a grill, table, couch, and firepit. Multi video game system. There is a community lake, playground, and hiking trail. We have two stand-up paddle boards, 1 adult kayak, and 1 child kayak. Pack n' play and high chair available.

Guest favorite

The log cabin features a green metal roof and a front porch with a wooden railing. Flower beds with pink blossoms are visible, complementing the natural surroundings. The cabin is situated in a park-like setting, surrounded by trees and lush greenery.

Cabin in Tracy City

4.95 out of 5 average rating, 118 reviews

Calming Cabin — Peaceful…Comfy…Caverns Near By

Park-Like, Relaxing Setting | Convenient to Hikes, Waterfalls, and The Caverns • Private — Full-Size Log Cabin • Front Porch Swing • Fire-pit, Picnic Table & Gas Grill • Convenient Amenities • 1GB Internet/WiFi • Full Kitchen, Ready to Cook • Loft Space w/Cozy Queen Futon • Spacious Yard • Hiking, Waterfalls, Rock Climbing—Close By • 7 min. Drive From Interstate • 15 min. from The Caverns & Sewanee Uni • Private Parking; Room for RV/Hauler • Small-Town Friendliness & Dining Close By

Superhost

The exterior of a two-story cabin is seen, featuring a sloped roof and a welcoming front porch with two chairs. Surrounding the cabin, a well-maintained lawn and gravel pathway create an inviting atmosphere amidst a wooded landscape.

Cabin in Winchester

4.82 out of 5 average rating, 157 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.

Superhost

A spacious outdoor deck features plush seating arrangements and a hot tub, with scenic views framed by trees. Soft lighting hangs above, creating an inviting atmosphere as the sun sets over the landscape. Nearby, a fire pit with seating offers a cozy gathering spot.

Cabin in Altamont

4.89 out of 5 average rating, 27 reviews

Mossy Falls Cabin | Outdoor Hot Tub & Fire Pit!

Step into a world of adventure and peace at Mossy Falls Cabin. Nestled within a 700-acre wood, it's a perfect escape to unplug and explore. Indulge in the artistic interiors, or venture onto your private deck with spectacular views. You'll hike through scenic trails, explore hidden waterfalls, and unwind in the hot tub under the starry sky. This 3BR cabin is perfect for nature lovers and those longing to escape the city's hustle.

Superhost

A three-story home with a light-colored exterior and brown shutters is showcased. Two wooden garage doors complement the design. A neatly landscaped front yard features two evergreen shrubs beside the entrance. Large windows allow plenty of natural light into the living spaces.

Home in Winchester

4.6 out of 5 average rating, 5 reviews

The Mimosa @ Twin Creeks Resort w/ FREE BOAT*

*FREE BOAT - Any 2 or more nights booked and staying through May 31st, 2025 qualifies for one full day complimentary pontoon rental of your choosing, subject to terms & availability! This stylish place to stay is perfect for group trips, family reunions, or family vacations. With plenty of bedrooms, everyone will have plenty of space during their stay as well as large family rooms to get together for activities and fun!

Top guest favorite

A bright and welcoming entryway features light wood paneling and a patterned area rug. A closed door leads to a bathroom, while a front door with a glass panel allows natural light to fill the space. Two framed images adorn the walls, adding character.

Cabin in Monteagle

5 out of 5 average rating, 40 reviews

The Sandstone Chalet: Dog-Friendly w/ No Pet Fee!

Escape to our dog-friendly mountain cabin in Monteagle, TN, where your furry friends stay free! Nestled just 6 miles from Sewanee and 12 miles from The Caverns, our cabin offers the perfect blend of tranquility and adventure. Surrounded by lush forests and moments from renowned hiking trails and breathtaking waterfalls, this Laurel Lake area retreat is ideal for romantic getaways or fun-filled family vacations.

Guest favorite

A serene view of Tims Ford Lake is presented, showcasing calm waters reflecting the sky. Fluffy clouds float above a green shoreline, with a boat creating gentle ripples as it moves across the surface. The scene is framed by lush greenery on the banks.

Cabin in Winchester

4.96 out of 5 average rating, 26 reviews

Walkable to Lake | Cornhole | Jenga | 4-In-A-Row

Only a five-minute walk to magical Tims Ford Lake and Devil's Step Boat Launch, this hidden gem is one of Winchester's most exclusive secrets. Indulge yourself with our life-sized games including cornhole, giant Jenga, huge 4-In-A-Row, board games, charcoal grill, soaring vaulted ceilings, outdoor seating, puzzles, bear-themed balcony, wood deck, brand new 4K smart TV, and fully inspired chef's kitchen.

Guest favorite

The cabin is observed from an elevated angle, showcasing a welcoming front porch with a railing. Surrounding trees display autumn foliage. A gravel path leads up to the entrance. The structure features a pitched roof and multiple windows allowing natural light.

Cabin in Bryant

4.91 out of 5 average rating, 206 reviews

Big Time Hill Cabin with an indoor pool, hot tub,

SUNDAY check in ALLOWED. BIG TIME HILL CABIN is located inside Paradise Pointe is gated & on a mountain at tristate corner of AL/TN/GA. Walk our HIKING TRAIL to tristate corner & be in 3 states at once. Paradise Pointe has 1 HuGe INDOOR POOL HOUSE with outdoor deck. 19 rentals has access to pool house. Cabin has hot tub, WIFI, fireplace, charcoal grill & fire pit!

Superhost

An entertainment room with hardwood flooring is equipped with a ping-pong table and various game tables. Soft bean bags are positioned in one corner, while a wall-mounted TV is visible. The space is illuminated by recessed lighting and a ceiling fan, creating a comfortable environment.

Home in Winchester

4.33 out of 5 average rating, 3 reviews

Hook, Wine & Sinker-Sleeps 28, Dock, Hot Tub

Welcome to Hook, Wine, & Sinker, your ultimate lakeside escape! This charming 8,000 sq. ft retreat offers fun, relaxation, and amenities for larger groups or families, ensuring everyone has room to unwind and enjoy the lake. Enjoy the large hot tub, 2 game rooms, 2 fire pits, 4 kayaks, 4 paddleboards, and ample space to accommodate up to 28 people.