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 Front Royal
4.89 out of 5 average rating, 158 reviews♛Royal A-Frame♛HOT TUB★PetsOK★WoodStove★FASTwifi
Cottage in Clearville
4.92 out of 5 average rating, 254 reviewsGrouseland's Vacation Cottage
Farm stay in Stanardsville
4.96 out of 5 average rating, 513 reviewsGreeneHouse.POOL*HotTub*MTNviews*FarmGOATS*Hiking
Cabin in Shenandoah
4.9 out of 5 average rating, 371 reviewsRiver's Edge, perfect family spot on Shenandoah
Home in Baker
4.97 out of 5 average rating, 289 reviewsSecluded Hilltop Retreat: Log Cabin + Hot Tub
Cabin in Moorefield
4.94 out of 5 average rating, 411 reviewsBeautiful Log Cabin w/ Gorgeous Views & Hot Tub
Home in Chester Gap
4.95 out of 5 average rating, 196 reviewsThe Nest
Cabin in Berkeley Springs
4.93 out of 5 average rating, 469 reviewsHorizon Hill-Log Cabin w/Hot Tub & Views!
Family- and pet-friendly home rentals
Cabin in Capon Bridge
4.78 out of 5 average rating, 314 reviewsWV Mountain cabin
Cabin in Lost City
4.96 out of 5 average rating, 359 reviewsLog Cabin in Lost River w/ Indoor Fireplace
Yurt in Etlan
4.95 out of 5 average rating, 193 reviewsPeaceful Secluded Old Rag Retreat
Cabin in Luray
4.89 out of 5 average rating, 412 reviewsCozy Cabin on beautiful farmland w/ GOATS!
Home in Sperryville
4.97 out of 5 average rating, 239 reviewsMountaintop Retreat
Cabin in Upper Tract
4.96 out of 5 average rating, 304 reviewsPotomac Overlook Log Cabin At SMOKE HOLE, WV /WIFI
Cabin in Great Cacapon
4.92 out of 5 average rating, 241 reviewsRustic Cabin on Cacapon River for Private Getaway
Cabin in Stanley
4.89 out of 5 average rating, 238 reviewsThe Bavarian Inn at Shenandoah River
Family-friendly home rentals with a pool
Cottage in Bluemont
4.95 out of 5 average rating, 202 reviewsThe Cottage @ Red Gate Farm- Horse & Wine Country!
Loft in Bridgewater
4.94 out of 5 average rating, 497 reviewsPrivate Studio Apt Retreat
Cabin in Culpeper
4.97 out of 5 average rating, 159 reviewsComfortable and unique 1790's log cabin
Bungalow in Stanardsville
4.93 out of 5 average rating, 241 reviewsRomantic, Carriage House Studio at Fairhill Farm
Cabin in Frostburg
4.92 out of 5 average rating, 133 reviewsBig Savage Guest Cabin
Home in Leesburg
4.96 out of 5 average rating, 107 reviewsPotomac Overlook Farms: 6 BR, 10 Acre River Estate
Home in New Market
4.97 out of 5 average rating, 115 reviewsPeaceful Shenandoah Valley Getaway
Townhouse in Mercersburg
4.87 out of 5 average rating, 165 reviewsResort House
Quick stats about vacation rentals that are family-friendly in Winchester
Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
2.3K reviews
Nightly prices starting at
$70 before taxes and fees
Destinations to explore
- Baltimore Vacation rentals
- Cabins Vacation rentals
- Arlington Vacation rentals
- Charlottesville Vacation rentals
- Alexandria Vacation rentals
- Bethesda Vacation rentals
- Annapolis Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- Family-friendly rentals United States
- Family-friendly rentals Washington
- Family-friendly rentals Deep Creek Lake
- Family-friendly rentals Baltimore
- Family-friendly rentals Virginia
- Rentals with outdoor seating Winchester
- Cottage rentals Winchester
- Pet-friendly rentals Winchester
- Rentals with a washer and dryer Winchester
- House rentals Winchester
- Monthly Rentals Winchester
- Cabin rentals Winchester
- Apartment rentals Winchester
- Rentals with a patio Winchester
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes