
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.

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)

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.

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

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!

Lake Home, Dock, Theatre, Hot Tub, FirePit, Kayaks
Take it easy at this unique and tranquil getaway. This beautiful lake home is one of it's kind at Tim's Ford. The house is nestled in a quiet rural neighborhood with woods in the backyard. The dock is only a small golf cart ride away. Enjoy beautiful lake views at your own private dock! This house is equipped with an amazing home theatre system, game room, hot tub, fire pit, kayaks and plenty more amenities! Tim's Ford Dam is only one mile away and has a public boat launch for you :)

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*

Latitude Adjustment - Lake Cottage
Enjoy the lake with all the amenities you could dream of! At Twin Creeks resort & Marina offers three resort style pools, marina, restaurant all golf cart accessible, designer decorated home with all the comforts of home. Use the golf cart at your leisure, two kayaks for paddling on the lake. Enjoy sunsets on the lake, fires at the firepit, grilling on the patio, hiking around the resort. Family friendly with fold-a-away crib, toys, books and other things to entertain children.

The Coalmont Cabin - Romantic Lakefront Escape
The Coalmont is a 4 acre waterfront retreat on top of the South Cumberland Mountains of Tennessee, between Nashville and Chattanooga. This 460 sq ft "tiny" cabin sleeps up to 4. Amenities abound with boats, hot tub, fishing, zip line, lawn games, large decks for gathering, fire pit, and beautiful scenery. Perfect retreat for couples looking for a romantic getaway, families wanting to unplug and reconnect with quality time, or anyone looking for a quiet place to work remotely.

Dock on Lake! Walk to Downtown Shops/Rest/Movies!
Charming, *Pet Friendly* well-loved 1950s lake house on Tim’s Ford Lake. Walking distance to grocery and downtown movie theatre, boutiques, restaurants and library. Near Twin Creeks marina/restaurant where you can rent boats. While here, you can swim at the dock; play darts, checkers or fuse ball; go out on the lake; walk to the Oldham Theatre; go hiking in Tim’s Ford State Park or nearby Sewanee; go to the Tullahoma drive-in theatre; or visit nearby Jack Daniel’s distillery.

Clean Lines and Simple Comfort
This 2 bed, 2 bath apartment duplex is located just two miles from Tims Ford Lake. Whether you’re in town for a weekend or an extended stay, this space offers everything you need for a relaxing and comfortable visit. Each room features a comfortable queen bed, fresh linens and ample closet space. The kitchen is stocked with cookware, stainless steel appliances, and a coffee maker for your morning brew. Book your stay and enjoy an experience that’s clean with a blend of style.

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.

Lovely Lake View Home at Twin Creeks Marina
This Craftsman-style, lake-view house is located in the private, gated lakeside community of Twin Creeks Village at scenic Tim's Ford Lake in Winchester, TN. It features an open floor plan with 4 bedrooms, 3 baths, game room, screened porch and huge deck overlooking the lake. Use the included golf cart to go to the swimming pools, marina, bar & grill or on-site convenience store. Information on boat & jet ski rentals are available at the marina shop.
Popular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

Hot tub, game room, fire pit and amazing view!

3-BR Luxury Home with Hot Tub & Arcade Games

Modern Treehouse • Epic Views • Hot Tub

Still Waters Tiny Home: Waterfront/Kayaks/HotTub

Modern Monteagle A-frame with Hot Tub

Martin Springs Cabin.

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

Where Tiny Living Meets Big Lake Escapes
Family- and pet-friendly home rentals

Sweet Dee's Tiny Home

Phelps Pharm, I Was Almost A Treehouse

Little Green Cottage

Cozy Cabin close to Tims Ford Lake & Jack Daniels

2BR Nature Getaway in Tiny Home w/ Lake access

Come Stay & Play at the farm

The Nest at The Retreat @ Deer Lick Falls

Waterfall Log Cabin
Family-friendly home rentals with a pool

TC Easy Breeezee

Barefoot Dreams

Family Fun! Private Pool, Hot Tub, Fire Pit

Forest Retreat: Poolside Bliss Close to Campus

The Modern Mainstay at Barefoot Bay

Private indoor pool & sauna

The Mimosa @ Twin Creeks Resort w/ free pontoon!

EASY PEASY on Tim's Ford Lake, golf cart, pool
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ735 | ﺩ.ﺇ735 | ﺩ.ﺇ735 | 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!
Destinations to explore
- Augusta Vacation rentals
- Western North Carolina Vacation rentals
- Nashville Vacation rentals
- Atlanta Vacation rentals
- Gatlinburg Vacation rentals
- Charlotte Vacation rentals
- Pigeon Forge Vacation rentals
- Asheville Vacation rentals
- Louisville Vacation rentals
- Southern Indiana Vacation rentals
- Cincinnati Vacation rentals
- Upstate South Carolina Vacation rentals
- Rentals with a patio Winchester
- Rentals with pools Winchester
- House rentals Winchester
- Pet-friendly rentals Winchester
- Rentals with a washer and dryer Winchester
- Rentals with lake access Winchester
- Rentals with outdoor seating Winchester
- Rentals with a fire pit Winchester
- Cabin rentals Winchester
- Rentals with a kayak Winchester
- Rentals with a fireplace 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
- Chattanooga Choo Choo
- Coolidge Park
- Rock City
- Hunter Museum of American Art
- Creative Discovery Museum
- South Cumberland State Park
- Raccoon Mountain Caverns & Campground
- Chattanooga Zoo
- U.S. Space & Rocket Center
- Point Park
- Dublin Park
- Cathedral Caverns State Park
- Chattanooga Whiskey Experimental Distillery
- Cumberland Caverns
- Burritt on the Mountain
- Old Stone Fort State Archaeological Park
- Huntsville Botanical Garden
- Finley Stadium
- Lowe Mill Arts And Entertainment
- Discovery Center
- Short Mountain Distillery




