Family-friendly holiday 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.
Holiday 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
Home in Lookout Mountain
4.96 out of 5 average rating, 658 reviewsCloudland Cottage
11–18 Oct
Cabin in Chattanooga
4.81 out of 5 average rating, 263 reviewsCozy Mountain Retreat w/ Spa
11–18 Oct
Home in Wildwood
4.85 out of 5 average rating, 383 reviewsThe Bedrock Cave Cottage
21–28 Sep
Cabin in Bryant
4.87 out of 5 average rating, 94 reviewsElk Ridge No Sunday Check In 25 mi fromChattanooga
11–18 Jan
Home in Lookout Mountain
4.87 out of 5 average rating, 123 reviews🥇5bdrm HotTub~22ppl🚗⚡️🔌STONE BROOK
14–21 Jul
Cabin in Spencer
4.79 out of 5 average rating, 85 reviewsHemlocks and a Hot Tub <5mi to Fall Creek Falls SP
5–12 Oct
Bungalow in Wildwood
4.85 out of 5 average rating, 463 reviewsThe Cavern on the Green. Ancient architecture
22–29 Sep
Cabin in Bryant
4.91 out of 5 average rating, 171 reviewsSpectacular! INDOOR POOL,HOTTUB! Chatt Tn 21 miles
1–8 Nov
Family- and pet-friendly home rentals
Farm stay in Fayetteville
4.85 out of 5 average rating, 357 reviewsCreek-Side Tiny House A *staycation* on Horse Farm
24–31 Jan
Cabin in Tracy City
4.86 out of 5 average rating, 294 reviewsMoonshine Runners Cabin
8–15 Aug
Home in Flintstone
4.94 out of 5 average rating, 357 reviews★ Mountain View Cottage ★
8–15 Jul
Home in Dunlap
4.8 out of 5 average rating, 122 reviewsThe Cozy Little House
17–24 Aug
Condo in Chattanooga
4.83 out of 5 average rating, 203 reviewsNorth Chatt Getaway
14–21 Jun
Guesthouse in Dunlap
4.98 out of 5 average rating, 176 reviewsThe Bird House near Fall Creek Falls State Park
28 Jan – 4 Feb
Home in McMinnville
4.92 out of 5 average rating, 127 reviewsThe Farm House at Pleasant Cove
17–24 Oct
Farm stay in McMinnville
4.96 out of 5 average rating, 154 reviewsThe Getaway at the Collins River Tree Farm
5–12 Jun
Family-friendly home rentals with a pool
Home in Chattanooga
4.79 out of 5 average rating, 565 reviewsWauhatchie Blue House | Lookout Mtn. Hot Tub
10–17 Feb
Cabin in Bryant
4.95 out of 5 average rating, 141 reviewsChatt. Tn 21 miles! Pool*AweSOME*HotTub*FirePit!!!
23–30 Sep
Home in Chattanooga Valley
5.0 out of 5 average rating, 40 reviewsLookout 3bdrm Chatt Valley Home 5m to TN w/ Pool
5–12 Nov
Townhouse in Chattanooga
4.72 out of 5 average rating, 359 reviewsUrban Retreat ★2BR/1BA★Fire Pit★King★W/D★Parking
5–12 Aug
Cabin in Bryant
4.82 out of 5 average rating, 51 reviewsPOOL*Hot tub* Rock Climb* Slide! Chatt Tn 21 miles
19–26 Oct
Cabin in Bryant
4.93 out of 5 average rating, 95 reviewsINDOOR POOL,MAGNIFICENT,HOT TUB! Chatt Tn 21 miles
14–21 Oct
Home in Chattanooga
4.54 out of 5 average rating, 110 reviewsUrban Nest-3BR/2BA-Sleeps 8-W/D-King Bed-Mt. View
3–10 Oct
Quick stats about holiday rentals that are family-friendly in Winchester
Total rentals
110 properties
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
30 properties allow pets
Total number of reviews
2.3K reviews
Nightly prices starting at
$117 NZD before taxes and fees
Destinations to explore
- Chattanooga Holiday rentals
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