
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

Modern Mountaintop Retreat ~ Hot Tub ~ Deck

35 Acres, Additional River Lot, Hot Tub, Pets OK

Grouseland's Pondside Vacation Cottage

Lost River Modern - a Modern Prefab

Cozy Cabin Hidden Away on a Lake!

Secluded Starry Sky, Near Luray, Hottub, FastWi-fi

Cozy Log Cabin with Modern Style

"Walden" Relax & Unwind in Private Couples Retreat
Family- and pet-friendly home rentals

Escape to Vista Grande with beautiful views

Gayte House Gay Owned, Liberal Oasis

Stunning Shenandoah Riverfront Retreat

Rustic Cabin on Cacapon River for Private Getaway

Outdoor Basecamp at Tiny Hidden Ridge

Stone School House - Minutes from Harper's Ferry

Modern Farmhouse near Shenandoah Nat'l Park + Lake

Log Cabin in Lost River w/ Indoor Fireplace
Family-friendly home rentals with a pool

Log Cabin Lodge That Has It All

Private Studio Apt Retreat

The Historic Booth House at the Harpers Ferry KOA

Log Cabin, *Pool, Hot Tub* Views, Views, Log Fires

Potomac Overlook Farms: 6 BR, 10 Acre River Estate

Monet Suite, elegnt lrg 2rm suite/blcny in villa

Tree top home in Massanutten next to tubing

Yurt*POOLpeace*FARM*horses*goats*woods*STARS*Hotub
Quick stats about vacation rentals that are family-friendly in Winchester
Total rentals
40 properties
Nightly prices starting at
$82 CAD before taxes and fees
Total number of reviews
2.8K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Family-friendly rentals Virginia
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- Luray Caverns
- Cunningham Falls State Park
- Stone Tower Winery
- Cacapon Resort State Park
- Robert Trent Jones Golf Club
- Gambrill State Park
- Bryce Resort
- Whiskey Creek Golf Club
- South Mountain State Park
- Creighton Farms
- Sly Fox Golf Club
- Shenandoah Valley Golf Club
- Berkeley Springs State Park
- Whitetail Resort
- Bowling Green Country Club
- Notaviva Vineyards
- Dinosaur Land
- River Creek Club
- Twin Lakes Golf Course
- Car and Carriage Caravan Museum
- Herndon Centennial Golf Course
- Reston National Golf Course
- The Golf Club at Lansdowne
- JayDee's Family Fun Center