
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 $83 AUD 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, Wifi 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.
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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.
KitchenFamilyQuiet

The Winchester Pad
The Winchester Pad is a spacious, modern townhouse ideally located within walking distance to the city centre and rail station to London. There is good road access in/out of the city and two free car parking permits are provided. Guests love it; with genuine accommodation all to themselves for 8 guests in 4 bedrooms and all the facilities required for an enjoyable stay. We welcome families, couples or 'professionals' from around the world seeking accommodation in this friendly, bustling city.
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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.
KitchenIndoor spacesComfort

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.
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Bay Tree, fabulous, modern 4 bed house, Winchester
Bay Tree is a spacious house in a quiet semi-rural location close to Winchester. Please do not book for a party or loud gathering. There are four bedrooms (six beds) two with ensuites, a downstairs shower wet room, well equipped kitchen, separate utility room and a large lounge/diner. The house has an enclosed private garden with decking & bbq. There is a trampoline for children to play on in the next garden. Towels and linen provided for guest use. On drive parking for two standard cars.
KitchenFamilyValue

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.
Indoor spacesKitchenSleep quality

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 spacesFamilySleep quality

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.
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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.
KitchenIndoor spacesCleanliness

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

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!
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Popular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

Ultra luxury, newly refurbished country retreat
KitchenFamilySleep quality

Cedar House - Pool & Spa Complex
FamilyKitchenGetting around

A Unique Farm Retreat
KitchenIndoor spacesLocation

Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB
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The Joinery, Owslebury, Winchester
KitchenIndoor spacesHiking

The Pool House: Contemporary country escape
Indoor spacesFamilyCheck-in

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath
KitchenIndoor spacesParking

80 acre Wood, Dutchtub, Lake, Treehouse & Zip-line
Indoor spacesKitchenCondition
Family- and pet-friendly home rentals

Idyllic Hideaway Ham Green Cottage near Winchester
FamilyKitchenQuiet

The Hayloft - Rural retreat very near Winchester
KitchenFamilyGetting around

Oak Framed Barn with Tennis Court
KitchenFamilySleep quality

The Nest
Indoor spacesKitchenLayout

Daily Red Kite Feed & Pool - Countryside Apartment
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The Annexe - Unique and Tranquil Getaway.
FamilyIndoor spacesCheckout

Iconic Beach Front Stay | The Watch House, Lepe
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The Barn @ North Lodge -Soho Farmhouse-esque Cabin
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Family-friendly home rentals with a pool

The Pool House (for 2 Adults & 2 Children)
KitchenFamilyNearby

Grayswood Cowshed in stunning Grounds
Indoor spacesKitchenOutdoor spaces

Sandy Balls Holiday Village New Forest Hampshire
FamilyIndoor spacesAmenities

Charming cottage with pool in the New Forest
KitchenFamilyParking

Cottage Pye - Beautiful Barn In The New Forest
KitchenFamilyCheck-in

Delightful one bedroom barn with beautiful views
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Secluded Country Cottage
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Beautiful S.Downs Cottage, pool and tennis
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When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $336 AUD | $309 AUD | $320 AUD | $357 AUD | $359 AUD | $372 AUD | $353 AUD | $400 AUD | $363 AUD | $336 AUD | $313 AUD | $353 AUD |
| 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
- Townhouse rentals Winchester
- Apartment 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
- University of Oxford
- Thorpe Park Resort
- Stonehenge
- South Downs National Park
- Southbourne Beach
- Windsor Castle
- LEGOLAND® Windsor Resort
- Boscombe Beach
- Lower Mill Estate
- Bracklesham Bay
- Hampton Court Palace
- Highclere Castle
- Mudeford Quay
- Chessington World of Adventures Resort
- Winchester Cathedral
- The Tank Museum
- Ascot Racecourse
- Bournemouth International Centre





