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
Farm stay in Stanardsville
4.96 out of 5 average rating, 515 reviewsGreeneHouse.POOL*HotTub*MTNviews*FarmGOATS*Hiking
Cottage in Clearville
4.92 out of 5 average rating, 257 reviewsGrouseland's Vacation Cottage
Cabin in Shenandoah
4.9 out of 5 average rating, 375 reviewsRiver's Edge, perfect family spot on Shenandoah
Chalet in Great Cacapon
4.94 out of 5 average rating, 375 reviewsFern Haven - Waterfront Chalet w/ WiFi & Hot tub!
Cabin in Berkeley Springs
4.93 out of 5 average rating, 472 reviewsHorizon Hill - Log Cabin w/Hot Tub & Views!
Home in Chester Gap
4.95 out of 5 average rating, 198 reviewsThe Nest
Home in Baker
4.97 out of 5 average rating, 289 reviewsSecluded Hilltop Retreat: Log Cabin + Hot Tub
Cottage in Confluence
4.82 out of 5 average rating, 130 reviewsYough Lake/Ohiopyle/ Stream Side Cottage/ Hot Tub
Family- and pet-friendly home rentals
Home in The Plains
4.89 out of 5 average rating, 190 reviewsRustic in the City
Cabin in Upper Tract
4.96 out of 5 average rating, 306 reviewsPotomac Overlook Log Cabin At SMOKE HOLE, WV /WIFI
Cabin in Lost City
4.96 out of 5 average rating, 359 reviewsLog Cabin in Lost River w/ Indoor Fireplace
Cabin in Luray
4.89 out of 5 average rating, 414 reviewsCozy Cabin on beautiful farmland w/ GOATS!
Home in Sperryville
4.98 out of 5 average rating, 240 reviewsMountaintop Retreat
Cabin in Great Cacapon
4.92 out of 5 average rating, 243 reviewsRustic Cabin on Cacapon River for Private Getaway
Guesthouse in Highland
4.98 out of 5 average rating, 265 reviewsWoodland Retreat
Apartment in Thomas
4.99 out of 5 average rating, 470 reviewsDandy Flats - The Nonchalant
Family-friendly home rentals with a pool
Cabin in Culpeper
4.97 out of 5 average rating, 159 reviewsComfortable and unique 1790's log cabin
Loft in Bridgewater
4.93 out of 5 average rating, 499 reviewsPrivate Studio Apt Retreat
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
Cabin in Davis
4.78 out of 5 average rating, 447 reviewsSki Chalet Cabin Canaan Valley 35 -Dog Friendly
Cottage in Bluemont
4.95 out of 5 average rating, 203 reviewsThe Cottage @ Red Gate Farm- Horse & Wine Country!
Home in Leesburg
4.96 out of 5 average rating, 108 reviewsPotomac Overlook Farms: 6 BR, 10 Acre River Estate
Home in Oakland
4.95 out of 5 average rating, 192 reviewsPrivate|LAKE&Waterfalls|Firewood|PoolAccess|HotTub
Quick stats about holiday rentals that are family-friendly in Winchester
Total rentals
30 properties
Wi-Fi availability
30 properties include access to Wi-Fi
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
$114 NZD before taxes and fees
Destinations to explore
- Baltimore Holiday rentals
- Cabins Holiday rentals
- Arlington Holiday rentals
- Charlottesville Holiday rentals
- Alexandria Holiday rentals
- Bethesda Holiday rentals
- Annapolis Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday 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 a washing machine and dryer Winchester
- Cottage rentals Winchester
- Monthly Rentals Winchester
- Cabin rentals Winchester
- House rentals Winchester
- Rentals with outdoor seating Winchester
- Pet-friendly rentals Winchester
- Rentals with a patio Winchester
- Apartment rentals Winchester
- 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