
Family-friendly holiday rentals in Winchester
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Winchester

Total holiday rentals
Explore 160 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $105 NZD per night before taxes and fees

Verified guest reviews
Over 7,620 verified reviews to help you choose

Pet-friendly accommodation
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
160 of Winchester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Winchester rentals

4.8 Average rating
Winchester stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated family-friendly rentals in Winchester
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Spacious central 2 bedroom apartment+ free parking
A spacious family-friendly 2 double/twin bedroom first floor flat located in the lovely Hyde area of central Winchester. Provides easy access to the city centre with all that the city offers. Only 5 minutes stroll to the train station. This apartment is close to all the historical sites and wide variety of restaurants and cafes which you'll enjoy as well as the cathedral and its impressive grounds. Winchester Christmas market and the city's magical atmosphere should be on everybody's calendar.
KitchenIndoor spacesCheck-in
4.96 out of 5 average rating, 187 reviews
Central, Quiet & Self-Contained
Incredibly central location. Only 150m from Cathedral & 200m to High St. Quiet: Set back from the street, double glazing, detached building. King size bed with luxury mattress & topper, hypoallergenic duvet & pillows, Egyptian cotton bedlinen and fluffy towels. Work space. Reading & soft lighting. Well Equipped: Tea & Coffee Facilities, Mini Fridge, TV (Netflix only) Iron+Board, Hairdryer, Toiletries & Fan. Secure parking subject to availability £20per night. NB. Access via external staircase.
Indoor spacesKitchenBathroom
4.92 out of 5 average rating, 159 reviews
The Queen Bee with off road parking
A peaceful and self contained home situated in a cul-de sac, conveniently located just 23 mins walk from central Winchester or 7 mins walk to bus stop ( every 15mins). Local amenities include Waitrose, pharmacy, wide range of restaurants/take away. Pub offering food within 15 mins walk or country pubs within 10 mins drive. On site parking, outside area with BBQ for alfresco dining. This is a newly furnished property with a king size bed upstairs, bed settee, kitchen area, bathroom with shower.
KitchenFamilyBarbecue
4.97 out of 5 average rating, 262 reviews
The Loft with free off road parking
A self-contained studio by apartment with kitchen facilities, double bed, sofa and TV. En-suite toilet and shower room. Free off street parking on the doorstep. Situated 5-10 minutes walk from Winchester's historic city centre and even closer to the widely renowned Black Boy pub. Within 150 metres of the South Downs Way. Just a few minutes walk from the Everyone Active Winchester Sports Centre. The apartment is accessed via an external staircase and so may not suit those with mobility issues.
KitchenIndoor spacesTV
4.92 out of 5 average rating, 331 reviews
Own Front Door
Welcome to the beautiful city of Winchester! I have self contained central accommodation comprising of a double bedroom with en-suite shower room, a lounge with fridge/tea/coffee making facilities and your own private front door accessed from the street at ground level. The accommodation has been part of a massive renovation of the main house, now fully completed. Dating from the 1850’s it still retains a Victorian feel with high ceilings and sash windows. It is a lovely light, airy space.
FamilyKitchenLayout
4.97 out of 5 average rating, 466 reviews
4 Bed City House with Private Garden and Parking
Discover our beautifully decorated four-bedroom home in Winchester's historic city centre. Enjoy the convenience of two rare parking spaces and a courtyard garden to unwind in. Indulge in the city's amenities that are just a stone's throw away, from artisan coffee shops to chic restaurants. Winchester Cathedral is only a leisurely five-minute stroll away! Whether for leisure or business, our spacious home offers comfort and convenience. Experience Winchester's charm and book your stay today!
Indoor spacesFamilyCleanliness
4.93 out of 5 average rating, 110 reviews
The Sky Penthouse, City Centre Luxury
Positioned right in the heart of charming historic Winchester The Sky Penthouse offers luxury modern comfortable 5 star accommodation . Private parking for one car . Positioned an easy level 300 meter walk from the main High Street within the City Centre , 400 meters from Winchester Cathedral and 500 meters from Winchester train station. Great location with a garden. Guests can choose the bed configuration of both the double bedrooms, either 6ft wide super king luxury beds or single beds.
Indoor spacesFamilyDecor
5.0 out of 5 average rating, 110 reviews
Central Winchester 1 Bedroom Home with own parking
Welcome to your lovely detached one bedroom home in a quiet leafy private road on the edge of St Giles Hill - just above medieval Winchester and on the edge of beautiful the South Downs Way. Your self-contained home includes parking on the drive, a stylish double bedroom, shower room, living area (with full double-width sofa bed) incorpoating a full kitchen/washing machine. Its an easy 10 minute downhill stroll across the park (lovely for a sunset picnic) to historic Winchester.
KitchenIndoor spacesAmenities
4.95 out of 5 average rating, 778 reviews
Central Winchester garden flat, permit parking
Winchester City Centre- Bijou, charming, characterful, homely, warm and cosy self contained one bedroom flat with free permit parking and luxuriously large bath tub with shower, private garden with patio for alfresco dining. Fully equipped galley kitchen for self - catering. Only a five minute level walk to the central High Street and Cathedral, with the world famous Christmas Market through November and December. Less than ten minutes walk from the Railway Station.
Indoor spacesFamilyNearby
4.95 out of 5 average rating, 429 reviews
Stylish Apartment • Central Winchester
Situated in the heart of Winchester, this newly refurbished two-bedroom apartment with its own private entrance offers a stylish and comfortable stay for couples, friends and families. Modern décor and thoughtful design create a cosy space to relax after exploring the city’s historic streets, shops and cathedral. You’re just steps from the popular St James Tavern, a welcoming traditional pub serving excellent locally sourced food.
Indoor spacesFamilySleep quality
4.92 out of 5 average rating, 263 reviews
The Hidden house in Winchester
The Hidden House is a slice of modern luxury tucked away in the heart of Winchester. Detached and private, this space is perfectly placed for exploring Winchester and all it has to offer. Our guests also love hiding away and making use of the big TV setup and Hotel Chocolat Velvetiser! Don't take our word for it - check out our reviews. Winchester High Street/The Cathedral - 10 min walk Winchester Train Station - 5 min walk
KitchenIndoor spacesCheckout
4.95 out of 5 average rating, 306 reviews
The Cottage in Compton
Come and enjoy a stay in The Cottage, located in the grounds of our 17th Century converted Barn. Enjoy a unique location on the edge of Winchester with direct access to the countryside. The Cottage has been recently extended and refurbished with everything you will need to make your stay enjoyable. A perfect place for a break to explore all the wonderful things that Winchester has to offer!
KitchenIndoor spacesDecor
4.99 out of 5 average rating, 224 reviewsPopular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

Stable Apartment with Hot Tub near Winchester
FamilyIndoor spacesBreakfast
4.92 out of 5 average rating, 287 reviews
Ultra luxury, newly refurbished country retreat
KitchenFamilyHospitality
4.88 out of 5 average rating, 511 reviews
A Unique Farm Retreat
Indoor spacesKitchenSleep quality
4.95 out of 5 average rating, 384 reviews
Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB
KitchenFamilyAccuracy
4.91 out of 5 average rating, 106 reviews
Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath
KitchenIndoor spacesComfort
4.98 out of 5 average rating, 466 reviews
The Pool House: Contemporary country escape
FamilyKitchenView
4.97 out of 5 average rating, 235 reviews
A holiday home in New Forest with pool & hot tub
FamilyKitchenGetting around
4.91 out of 5 average rating, 203 reviews
The Joinery, Owslebury, Winchester
Indoor spacesFamilyHot tub
4.86 out of 5 average rating, 304 reviewsFamily- and pet-friendly home rentals

Idyllic Hideaway Ham Green Cottage near Winchester
Indoor spacesFamilyLaundry
4.97 out of 5 average rating, 600 reviews
The Old Tractor Barn - Rural holiday accommodation
KitchenFamilyTV
4.94 out of 5 average rating, 232 reviews
Oak Framed Barn with Tennis Court
Indoor spacesFamilyOutdoor spaces
4.94 out of 5 average rating, 412 reviews
Iconic Beach Front Stay | The Watch House, Lepe
FamilyIndoor spacesPool
4.98 out of 5 average rating, 153 reviews
Daily Red Kite Feed & Pool - Countryside Apartment
FamilyIndoor spacesAccuracy
4.96 out of 5 average rating, 290 reviews
The Barn @ North Lodge -Soho Farmhouse-esque Cabin
FamilyIndoor spacesGetting around
4.96 out of 5 average rating, 658 reviews
The Nest
Indoor spacesFamilyBathroom
4.81 out of 5 average rating, 162 reviews
The Annexe - Unique and Tranquil Getaway.
Indoor spacesFamilyOutdoor spaces
4.94 out of 5 average rating, 153 reviewsFamily-friendly home rentals with a pool

The Pool House (for 2 Adults & 2 Children)
Indoor spacesKitchenCondition
4.98 out of 5 average rating, 120 reviews
Sandy Balls Holiday Village New Forest Hampshire
KitchenIndoor spacesComfort
4.99 out of 5 average rating, 218 reviews
Grayswood Cowshed in stunning Grounds
FamilyIndoor spacesCleanliness
4.98 out of 5 average rating, 363 reviews
Charming cottage with pool in the New Forest
Indoor spacesFamilyCondition
4.98 out of 5 average rating, 106 reviews
Rural Isle of Wight cottage with indoor pool use
FamilyIndoor spacesAccuracy
4.99 out of 5 average rating, 141 reviews
Luxury Pool House set in an Oxfordshire forest
Indoor spacesKitchenCondition
4.97 out of 5 average rating, 104 reviews
Delightful one bedroom barn with beautiful views
KitchenFamilyLocation
4.94 out of 5 average rating, 161 reviews
Comfortable 1-Bedroom Guest Suite in rural setting
FamilyIndoor spacesHospitality
4.96 out of 5 average rating, 193 reviewsWhen is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $424 NZD | $389 NZD | $403 NZD | $450 NZD | $452 NZD | $469 NZD | $445 NZD | $504 NZD | $457 NZD | $424 NZD | $394 NZD | $445 NZD |
| Avg. temp | 5°C | 5°C | 7°C | 9°C | 12°C | 15°C | 17°C | 17°C | 15°C | 11°C | 8°C | 5°C |
Destinations to explore
- Condo rentals Winchester
- Rentals with breakfast Winchester
- Pet-friendly rentals Winchester
- Cabin rentals Winchester
- Villa rentals Winchester
- Cottage rentals Winchester
- House rentals Winchester
- Apartment rentals Winchester
- Townhouse rentals Winchester
- Family-friendly rentals Hampshire
- Family-friendly rentals England
- Family-friendly rentals United Kingdom
- New Forest National Park
- Bournemouth Beach
- West Wittering Beach
- Paultons Park Home of Peppa Pig World
- Longleat Safari Park
- Goodwood Motor Circuit
- Thorpe Park Resort
- University of Oxford
- South Downs National Park
- Stonehenge
- Southbourne Beach
- Windsor Castle
- LEGOLAND® Windsor Resort
- Lower Mill Estate
- Boscombe Beach
- Bracklesham Bay
- Hampton Court Palace
- Highclere Castle
- Chessington World of Adventures Resort
- Mudeford Quay
- Winchester Cathedral
- The Tank Museum
- University of Reading
- Ascot Racecourse





