
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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

Private lakefront log cabin w/dock & hot tub

3-BR Luxury Home with Hot Tub & Arcade Games

Tennessee’s Only Luxury Safari Tent Getaway

Still Waters Tiny Home: Waterfront/Kayaks/HotTub

Martin Springs Cabin.

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

Lakeside Tiny House

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

Granny's Guest House

Studio House

Nature’s Tiny Riverside Hideaway

Dock on Lake! Walk to Downtown Shops/Rest/Movies!

Return Guest House and Writers’ Retreat

Relax & Unwind in Cozy Farm Stay 7 mins from I-24

Secluded Country Cabin between city and country

The Nest at The Retreat @ Deer Lick Falls
Family-friendly home rentals with a pool

Hundred Oaks

Lakefront Haven–Fall Escape w/ Firepits + Kayak

Monteagle/Sewanee forest cottage with amenities

Heaven’s View Lodge, Pool, Pet Friendly

Tri-state Corner Cabin with a fire pit, hot tub, &

Lakeside Retreat Marina/Pool, Golf Cart, Game Room

Fall Vibes- Spa & Fire Place | Mins to Chattanooga

Luxe 2BR Cabin D by MHM Luxury Properties
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
Destinations to explore
- 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
- Harpeth River Vacation rentals
- Cincinnati Vacation rentals
- Southern Indiana Vacation rentals
- Chattanooga Vacation rentals
- House rentals Winchester
- Cabin rentals Winchester
- Rentals with a kayak Winchester
- Pet-friendly rentals Winchester
- Rentals with pools Winchester
- Rentals with a fireplace Winchester
- Rentals with a washer and dryer Winchester
- Rentals with a patio Winchester
- Rentals with outdoor seating Winchester
- Rentals with lake access Winchester
- Rentals with a fire pit 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
- Sweetens Cove Golf Club
- Black Creek Club
- Coolidge Park
- The Ledges
- Chattanooga Golf and Country Club
- Chattanooga Choo Choo
- The Lookout Mountain Club
- Old Fort Golf Course
- Creative Discovery Museum
- Hunter Museum of American Art
- National Medal of Honor Heritage Center