
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.

Unbeatable Charm & Convenience On The Square!
Escape to The Heritage Lofts, just off of the thriving Winchester square. Only minutes from Tims Ford Lake, this fabulously-renovated apartment has all of the comfort and amenities you need to feel right at home during your stay in Winchester. See the local scene in style with one of our bike or paddle board rentals, and shop til you drop on our thriving downtown square. Then grab a meal before relaxing in the comfortable confines of your spacious loft. There isn't a better spot to stay in town!

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)

Lakefront Haven | Hot Tub | Kayaks, Firepit
Welcome to Lakefront Haven! This home offers a seamless blend of comfort and luxury, providing a retreat for a lakefront getaway. • Lakefront property + beautiful views • Hot Tub • Fantastic community pool for the hot summer days • Screened in, heated porch with TV and sound system • Kayak, 2 Paddleboards and Peleton provided • Deck with gas Weber grill • Backyard firepit with chairs • Well equipped kitchen • Less than two miles from Twin Creeks Marina • Walkable to the downtown Square

Tiny House
You will feel right at home in this adorable Tiny Home with RV Hookups! This picture-perfect little cottage has a bedroom with queen size bed, full bath with tile walk-in shower, full kitchen with all of the amenities, and living room with queen size sleeper sofa. The back porch offers peace, quiet, and spectacular mountain views. This property is super convenient to Tims Ford Lake, The Caverns music venue, Jack Daniels Distillery, University of the South, and historic downtown Winchester.

Best Views on Lake, TIki Hut, Boat Rental + More
If you are looking for the perfect getaway to a luxury lake home that has countless amenities and postcard like views then look no further! This newly renovated lake front home boasts the best views on the lake, tiki hut, multiple outdoor decks, covered patio, hot tub, game room, theatre, kayaks, SUPs and plenty more! We even have a 2022 Crest tritoon with a 200 HP motor that is available to rent for experienced boaters! This is truly a one of kind property. We look forward to serving you!

Private dock/gazebo on quiet cove. Tims Ford Lake!
Indulge in the tranquility of Tims Ford Lake, TN! Our exquisite 5-star cottage, just 6 miles from Tims Ford State Park/Marina, beckons you to unwind. Conveniently situated 18 miles from Tullahoma and 8 miles from Winchester, our boat-friendly haven features a private dock and a circular drive. Minimum rental age: 25. Ensure a seamless stay by signing our legal Rental Agreement and presenting a government-issued ID. Book now for a worry-free lakeside escape – your perfect retreat awaits!

Lakeside Retreat at The Reserve w/ Golf Cart
Beautiful lakeside home on Tim's Ford Lake! Short Walk or Golf Cart ride to Blue Gill Grill & Holiday Landing Marina. Boat Parking on the Driveway during your stay! First Floor: Master Bed with Full Bath, Dining Room, Living Room, Kitchen (Fully stocked with basic spices and cooking utensils). Outside Patio with Fire Place and seating. Second Floor: BR 2- King Bed. BR 3 Queen Bed, Loft Space, Sectional Couch, Pull out Queen. *No Smoking *Max 10 Guest *Front Door Security Cam*

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

The Hangout on Heath Lane
Enjoy a peaceful experience at this centrally-located home. The Hangout is half a mile from the beautiful Twin Creeks Marina and 1 mile to historic downtown Winchester! Other local attractions include: -Grab a coffee and enjoy a tasty breakfast or lunch at Walnut Hill Coffee Shop -For a delicious, upscale dinner, be sure to visit Filo's Tavern -Head out for a tour and tasting at Jack Daniels Distillery -Grab some tickets to the Cavern's for a memorable concert experience.

The Coalmont Cabin - Romantic Lakefront Escape
A quiet lakeside retreat made for slow mornings and star-filled nights. Wake to coffee on the deck as the fog drifts across the water, geese gather along the shoreline, and the world feels still for just a little longer. Spend your afternoons out on the lake, gliding through lily pads in a moment that feels like a scene from The Notebook. Tucked among the trees with a saltwater spa beneath the stars, The Cabin is where peaceful seclusion meets unforgettable memories.

Catch & Release - Spacious Lakefront Getaway
Escape to this bright, spacious 2BR/2BA lakefront retreat—one of the largest homes in the Retreat at Water’s Edge. Sip coffee on the screened porch, kayak or fish from the semi-private dock, and gather by the firepit at sunset. Minutes from world-class hiking, including the nationally acclaimed Fiery Gizzard Trail, yet set on a calm, family-friendly lake perfect for kids to explore and unplug. Ideal for couples, families, or both.

Homestead Haven
Enjoy your stay at Homestead Haven with a beautiful view of the farm. We have a 72 acre farm and a family business located walking distance from the airbnb. Take a short stroll down the hill to see the lovely plants and meet your host! This 2 bedroom guesthouse is the perfect stay for you and your loved ones. Conveniently located in Winchester, a short drive to the beautiful historic downtown Winchester and Tim’s ford Lake!
Popular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

Phelps Pharm, I Was Almost A Treehouse

Our Catty Shack

3-BR Luxury Home with Hot Tub & Arcade Games

Still Waters Tiny Home: Waterfront/Kayaks/HotTub

Modern Monteagle A-frame with Hot Tub

Cozy Tiny Home w/large deck, hot tub and firepit

Where Tiny Living Meets Big Lake Escapes

CABIN w/ AMAZING VIEWS, HOT TUB, FIRE PIT
Family- and pet-friendly home rentals

Little Green Cottage

Spectacular Mountain Top Cabin Getaway

Cozy Cabin close to Tims Ford Lake & Jack Daniels

Tadpole Cabin at Creek Road Farm

Martin Springs Cabin.

The Nest at The Retreat @ Deer Lick Falls

Escape Tiny

Riverfront Getaway with a View
Family-friendly home rentals with a pool

TC Easy Breeezee

Heaven’s View Lodge, Pool, Pet Friendly

Basecamp Retreat TimsFordLake

Barefoot Dreams

Fish Tales Cabin – Spacious Retreat with Hot Tub

Family Fun - Private Pool, Spa & Mountain Views

The Modern Mainstay at Barefoot Bay

Lovely Lake View Home at Twin Creeks Marina
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ654 | ﺩ.ﺇ595 | ﺩ.ﺇ709 | ﺩ.ﺇ701 | ﺩ.ﺇ970 | ﺩ.ﺇ1,149 | ﺩ.ﺇ1,146 | ﺩ.ﺇ1,065 | ﺩ.ﺇ801 | ﺩ.ﺇ830 | ﺩ.ﺇ837 | ﺩ.ﺇ687 |
| 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 |
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 ﺩ.ﺇ37 per night before taxes and fees

Verified guest reviews
Over 3,880 verified reviews to help you choose

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
70 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!
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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
- Coolidge Park
- Chattanooga Choo Choo
- Hunter Museum of American Art
- Point Park
- South Cumberland State Park
- Chattanooga Zoo
- Raccoon Mountain Caverns & Campground
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- Creative Discovery Museum
- Von Braun Center, North Hall
- U.S. Space & Rocket Center
- Huntsville Botanical Garden
- Lowe Mill Arts And Entertainment
- Cathedral Caverns State Park
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- Short Mountain Distillery
- Burritt on the Mountain
- Discovery Center
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- Chattanooga Convention Center
- Tennessee River Park





