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
Home in Sandleheath
4.96 out of 5 average rating, 223 reviewsOrchard Barn Spa, exclusively for you, New Forest
Oct 31 – Nov 7
Cabin in Reading
4.92 out of 5 average rating, 125 reviewsSummer cabin (S/C) with outdoor bbq & hot-tub
Apr 1 – 6
Home in Owslebury
4.89 out of 5 average rating, 210 reviewsThe Joinery, Owslebury, Winchester
Mar 22 – 29
Home in Swanwick
4.93 out of 5 average rating, 119 reviewsRiverside Cottage-Walks-Hot Tub
May 8 – 15
Home in Pitt
4.88 out of 5 average rating, 145 reviewsLuxury 3 Bedroom, Scandinavian Lodge with HOT TUB
Jun 5 – 12
Shepherd’s hut in Salisbury
4.95 out of 5 average rating, 798 reviewsShepherd's Hut with hot tub use near Stonehenge
Sep 6 – 13
Cottage in Baughurst
4.96 out of 5 average rating, 304 reviewsLuxury rural thatched cottage with cedar hot tub.
Jan 4 – 11
Guesthouse in Chippenham
4.97 out of 5 average rating, 420 reviewsThe Loft - Exceptional views, hot tub & balcony
Jun 2 – 9
Family- and pet-friendly home rentals
Guest suite in Houghton
4.97 out of 5 average rating, 149 reviewsSelf-Contained Pretty Annexe in Coopers Farmhouse
Dec 9 – 16
Cottage in Ibworth
4.94 out of 5 average rating, 138 reviewsSelf contained, rural cottage, 2 double bedrooms
Jul 23 – 30
Cottage in Hampshire
4.88 out of 5 average rating, 251 reviewsThatched cottage, Wherwell, Test Valley Hampshire
Oct 16 – 23
Cottage in Littleton Panell
4.95 out of 5 average rating, 104 reviewsModern and stylish cottage with courtyard garden
Dec 1 – 8
Bungalow in Burley
4.92 out of 5 average rating, 402 reviewsA Hidden Gem - Tranquil Barn in the New Forest
Jul 1 – 8
Cottage in Fittleworth
4.99 out of 5 average rating, 524 reviewsStylish Hideaway with an amazing woodland view
Dec 12 – 19
Religious building in Chittoe
4.96 out of 5 average rating, 229 reviewsThe North Transept
Nov 3 – 10
Home in Brook, Lyndhurst
4.94 out of 5 average rating, 477 reviewsHistory + Luxury Eco House in The New Forest
Apr 28 – May 5
Family-friendly home rentals with a pool
Tiny home in Soberton
4.94 out of 5 average rating, 198 reviewsThe Guest House, Five Trees
May 12 – 17
Barn in Hampshire
4.97 out of 5 average rating, 171 reviewsBeautifully converted 19th century barn,
Jun 4 – 11
Guesthouse in Rudgwick
4.94 out of 5 average rating, 214 reviewsBucks Green Place Beautiful Converted Barn
Dec 22 – 29
Apartment in Christchurch
4.88 out of 5 average rating, 230 reviewsRoom by the beach
Apr 7 – 14
Cottage in Chichester
4.9 out of 5 average rating, 238 reviewsPear Store cottage with pool & tennis
Oct 25 – Nov 1
Guesthouse in Swanage
4.86 out of 5 average rating, 143 reviewsSwanage Sands Vegetarian/Vegan Studio
Dec 17 – 24
Home in Hampshire
4.98 out of 5 average rating, 119 reviews- A Perfect Family Escape (Pool - Private Use)
Oct 14 – 21
Villa in Isle of Wight
4.95 out of 5 average rating, 249 reviews5* waterside luxury boathouse - pool & log-burner
Mar 16 – 23
Quick stats about vacation rentals that are family-friendly in Winchester
Total rentals
150 properties
Wifi availability
150 properties include access to wifi
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Total number of reviews
6.5K reviews
Nightly prices starting at
$30 before taxes and fees
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