Kid-friendly holiday rentals in Winchester

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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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Top Guest favourite

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.

Guest favourite

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 favourite

Cabin in Tracy City

4.95 out of 5 average rating, 118 reviews

Calming Cabin — Peaceful…Relaxing…Caverns Near By

Park-Like, Private Setting | Convenient to Hikes, Waterfalls, and The Caverns • Comfy — 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

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.

Guest favourite

Tiny home in Lookout Mountain

4.94 out of 5 average rating, 599 reviews

Lil' Haven at Tiny Bluff

Perched high on the brow on Lookout Mountain, our pet-friendly tiny house is packed with luxurious features and is surprisingly spacious. Lil' Haven is the perfect place to get away after a day in Chattanooga or a hike on the mountain. It’s a short drive down or along the mountain to best restaurants and state parks. Enjoy a meal out on the deck admiring the view, relax in the soaker tub, or simply sink back into the bed and stargaze through the skylights.

Superhost

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.

Guest favourite

Cabin in Winchester

4.96 out of 5 average rating, 27 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 favourite

Cabin in Lookout Mountain

4.94 out of 5 average rating, 230 reviews

Lookout Lazy Bear Cabin

Looking for a family or group of friends get away but close to Chattanooga, Rock city and Ruby Falls?? This is a cozy cabin in the woods away from everyone but close to everything! There is plenty to do outdoors! hiking, mtn biking, rock climbing, to name a few. The cabin is totally DISINFECTED and SANITIZED after each guest leaves for your safety. Come relax at our Lazy Cabin!!

Guest favourite

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

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.

Superhost

Cottage in Monteagle

4.92 out of 5 average rating, 48 reviews

Mountain Retreat

Great for family or spiritual retreats with lots of amenities. Just 6 minutes from I-24, yet off the beaten path. Close to University of the South, Sewanee, Tracy City, Bigfoot Adventure TN Zip Line and The Caverns Lots of hiking trails nearby: Fiery Gizzard/Foster Falls, Denny Cove, Grundy Lakes Historic Area, Lost Cove/Natural Bridge.

Guest favourite

Home in Tullahoma

4.95 out of 5 average rating, 117 reviews

Walnut Cove Cottage *with recently added hot tub*

Our cozy little cottage is in a secluded cove sitting on over an acre lot just a tenth of a mile from Holiday Landing Marina. *With newly added hot tub* Includes: *Golf Cart *Lighted Fire Pit Area (wood provided) *Horseshoe Pit *Large parking area for boats/jet skis * Screened-In back porch *Covered grill *Fully Stocked C offee Bar