
Family-friendly holiday rentals in Winchester
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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 $84 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, 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.
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.
4.92 out of 5 average rating, 157 reviews
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.
4.86 out of 5 average rating, 166 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.
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.
4.97 out of 5 average rating, 466 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.
5.0 out of 5 average rating, 110 reviews
Oak Framed Barn with Tennis Court
A stylish secluded, two storey, oak framed barn with tennis court, 4 miles from Winchester. Homely space with two bedrooms plus a sofa bed (upon request) and ground floor open plan living area. Super fast WiFi. The Barn adjoins the Watercress Way and stands separately in the grounds with views over open Hampshire fields. Nearest neighbour c.1 mile away but there is loads to do in the area with an abundance of country pubs, one or two within walking distance and beaches within 50 minutes
4.94 out of 5 average rating, 412 reviews
Stable Cottage Beauworth Southdowns Hampshire
Nestled within the South Downs National Park, this charming countryside escape offers uninterrupted views across open fields where sheep graze. Wake up to breathtaking bedroom views, explore the surrounding countryside and historic Winchester, and in the winter, cosy up beside the crackling log burner. Thoughtfully equipped for families with babies and children, as well as couples seeking a peaceful getaway, it’s the perfect retreat to unwind and enjoy Hampshire’s beautiful landscape.
4.99 out of 5 average rating, 136 reviews
Idyllic Hideaway Ham Green Cottage near Winchester
The Orchard Studio at Ham Green Cottage is a pretty brick and flint building tucked away in a corner of our truly English country garden. You are completely private. We are family-friendly and you can expect a comfortable stay and warm welcome. We are in a village close to the historic city of Winchester, however our setting is completely rural and quiet. We have a fantastic village pub or there are lots of places to chose from in Winchester itself - the best of both worlds!
4.97 out of 5 average rating, 600 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.
4.95 out of 5 average rating, 428 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.
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
4.95 out of 5 average rating, 306 reviewsPopular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

Stable Apartment with Hot Tub near Winchester
4.92 out of 5 average rating, 287 reviews
Ultra luxury, newly refurbished country retreat
4.88 out of 5 average rating, 511 reviews
Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB
4.91 out of 5 average rating, 106 reviews
A Unique Farm Retreat
4.95 out of 5 average rating, 385 reviews
The Pool House: Contemporary country escape
4.97 out of 5 average rating, 235 reviews
A cosy farm cottage, with lots of character.
4.99 out of 5 average rating, 245 reviews
The Joinery, Owslebury, Winchester
4.86 out of 5 average rating, 304 reviews
A holiday home in New Forest with pool & hot tub
4.91 out of 5 average rating, 202 reviewsFamily- and pet-friendly home rentals

Daily Red Kite Feed & Pool - Countryside Apartment
4.96 out of 5 average rating, 290 reviews
Peaceful barn conversion in rural location.
4.93 out of 5 average rating, 197 reviews
The Annexe - Unique and Tranquil Getaway.
4.94 out of 5 average rating, 152 reviews
The Nest
4.81 out of 5 average rating, 162 reviews
Iconic Beach Front Stay | The Watch House, Lepe
4.98 out of 5 average rating, 153 reviews
New Forest cottage by the green
4.97 out of 5 average rating, 393 reviews
Quaint Cosy Cottage in East Meon
4.97 out of 5 average rating, 190 reviews
The Barn @ North Lodge -Soho Farmhouse-esque Cabin
4.96 out of 5 average rating, 655 reviewsFamily-friendly home rentals with a pool

The Pool House (for 2 Adults & 2 Children)
4.98 out of 5 average rating, 120 reviews
Sandy Balls Holiday Village New Forest Hampshire
4.99 out of 5 average rating, 217 reviews
Charming cottage with pool in the New Forest
4.98 out of 5 average rating, 106 reviews
Grayswood Cowshed in stunning Grounds
4.98 out of 5 average rating, 363 reviews
Secluded Country Cottage
4.88 out of 5 average rating, 119 reviews
Cottage Pye - Beautiful Barn In The New Forest
4.87 out of 5 average rating, 156 reviews
Rural Isle of Wight cottage with indoor pool use
4.99 out of 5 average rating, 141 reviews
Comfortable 1-Bedroom Guest Suite in rural setting
4.96 out of 5 average rating, 192 reviewsWhen is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $340 AUD | $312 AUD | $323 AUD | $361 AUD | $363 AUD | $377 AUD | $357 AUD | $405 AUD | $367 AUD | $340 AUD | $316 AUD | $357 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
- 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
- University of Oxford
- Thorpe Park Resort
- Stonehenge
- South Downs National Park
- 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
- Ascot Racecourse
- University of Reading





