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
Cabin in Chattanooga
4.81 out of 5 average rating, 264 reviewsCozy Mountain Retreat w/ Spa
Feb 7 – 14
Farm stay in Morrison
4.96 out of 5 average rating, 302 reviewsPhelps Pharm Bunkhouse
Jan 20 – 27
Home in Lookout Mountain
4.96 out of 5 average rating, 658 reviewsCloudland Cottage
Aug 27 – Sep 3
Bungalow in Wildwood
4.85 out of 5 average rating, 463 reviewsThe Cavern on the Green. Ancient architecture
Feb 23 – Mar 2
Cabin in Bryant
4.87 out of 5 average rating, 95 reviewsElk Ridge No Sunday Check In 25 mi fromChattanooga
Apr 19 – 26
Home in Lookout Mountain
4.87 out of 5 average rating, 123 reviews🥇5bdrm HotTub~22ppl🚗⚡️🔌STONE BROOK
Aug 18 – 25
Cabin in Spencer
4.79 out of 5 average rating, 85 reviewsHemlocks and a Hot Tub <5mi to Fall Creek Falls SP
Aug 21 – 28
Home in Wildwood
4.85 out of 5 average rating, 383 reviewsThe Bedrock Cave Cottage
Dec 21 – 28
Family- and pet-friendly home rentals
Cabin in Tracy City
4.86 out of 5 average rating, 296 reviewsMoonshine Runners Cabin
Oct 2 – 9
Home in Flintstone
4.94 out of 5 average rating, 357 reviews★ Mountain View Cottage ★
Jul 18 – 25
Home in McMinnville
4.92 out of 5 average rating, 127 reviewsThe Farm House at Pleasant Cove
Aug 23 – 30
Cabin in Dunlap
4.91 out of 5 average rating, 213 reviewsCagle Mountain Cabin near Fall Creek Falls Park TN
Apr 25 – May 2
Home in Dunlap
4.8 out of 5 average rating, 123 reviewsThe Cozy Little House
Oct 19 – 26
Guesthouse in Dunlap
4.98 out of 5 average rating, 176 reviewsThe Bird House near Fall Creek Falls State Park
Nov 25 – Dec 2
Farm stay in McMinnville
4.96 out of 5 average rating, 154 reviewsThe Getaway at the Collins River Tree Farm
May 8 – 15
Home in Lookout Mountain
4.95 out of 5 average rating, 109 reviewsBest View In Chattanooga, Pet Friendly, 2BR 2BA
Apr 10 – 17
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
Nov 16 – 23
Cabin in Bryant
4.95 out of 5 average rating, 142 reviewsChatt. Tn 21 miles! Pool*AweSOME*HotTub*FirePit!!!
Sep 23 – 30
Home in Chattanooga Valley
5.0 out of 5 average rating, 41 reviewsLookout 3bdrm Chatt Valley Home 5m to TN w/ Pool
Nov 2 – 9
Cabin in Spencer
4.85 out of 5 average rating, 27 reviewsCABIN:FALL CREEK FALLS STATE PARK
Aug 3 – 10
Townhouse in Chattanooga
4.72 out of 5 average rating, 359 reviewsUrban Retreat ★2BR/1BA★Fire Pit★King★W/D★Parking
Jul 16 – 23
Cabin in Bryant
4.93 out of 5 average rating, 95 reviewsINDOOR POOL,MAGNIFICENT,HOT TUB! Chatt Tn 21 miles
Dec 21 – 28
Cabin in Bryant
4.82 out of 5 average rating, 51 reviewsPOOL*Hot tub* Rock Climb* Slide! Chatt Tn 21 miles
Jan 6 – 13
Home in Chattanooga
4.54 out of 5 average rating, 110 reviewsUrban Nest-3BR/2BA-Sleeps 8-W/D-King Bed-Mt. View
Aug 23 – 30
Quick stats about vacation 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
€ 65 before taxes and fees
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