
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.

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.

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.

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.

St Michael's Hall, City Centre
St Michael's Hall is a unique, newly renovated church hall in the heart of the historic city centre. A stone's throw from the Cathedral, College, buzzy high street and water meadows, it's the perfect base to explore everything Winchester and the surrounding area has to offer. Each bedroom has its own bathroom, meaning it's as suitable for two couples as it is for a romantic city break or four friends. One on-street parking permit is available, while the train station is a short walk away.

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.

Bright Bijou Studio in Central Winchester
A beautiful bright cosy studio apartment on one of the quietest streets in the centre of historic Winchester❤️. The breathtaking cathedral and other must-see sights are all within a flat 10 minute walk. Ideal for short stays or a weekend get-away. Just five minutes walk from train station/city centre, and 10 mins walk from the bus station. * Super-comfy double bed ✅ * Fast WiFi ✅ * Comfortable big chair and table for laptop working ✅ * Wide range of caf/decaf teas and coffees ✅

Stable Cottage Beauworth Southdowns Hampshire
Welcome to Stable Cottage, your idyllic getaway. Our newly built cottage is designed to the highest standard for your comfort and enjoyment. The cozy atmosphere is enhanced by super-insulated walls and a log-burning stove that keep you warm during colder months. In summer, the sliding patio doors let in sunshine and stunning views of the Hampshire countryside. Stay connected with super-fast fibre broadband and a Smart TV. Your stay at Stable Cottage will be unforgettable.

Room with a view
You’ll love sharing photos of this unique place with your friends. Room with a View is a cosy and bright studio room located in the outskirts of the rural village of Owslebury. Just a 5-mile drive from the medieval city of Winchester, Room with a View is situated in a prime location, perfect for a serene getaway or business stay. Secluded from the busy bustle of the city, yet a swift 10-minute drive, Room with a View is surrounded by acres of fields and beautiful views.

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.

Lovely guest room with own entrance
Lovely Newly Decorated Room with Ensuite – Eastleigh (SO50 6DJ) Enjoy your own private entrance to this newly decorated room with an ensuite. It comes with a small fridge, microwave, toaster, kettle, and tea/coffee. Super-fast mesh Wi-Fi (up to 200mbps) is provided. Keyless check-in with code sent after booking. Free roadside parking is available. The room features a soft water system. Only 1 mile to Eastleigh Train Station. 5-minute walk to River Itchen.

Pretty self contained annexe
Pretty, self contained annexe with its own entrance, located between the historic city of Winchester & Southampton and on the doorstep of the New Forest National Park. Great travel links - M3/M27, Southampton Airport & Southampton Parkway station. Studio comprises double bed, kitchen with oven, hob, fridge & microwave. Breakfast bar, which doubles as a workspace, shower room and shared use of patio and garden. We also have a young, bouncy dog!

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

Stable Apartment with Hot Tub near Winchester

Hacketts East Wing HotTub Bursledon Hamble River

Adorable Detached 1 bedroom Annexe with hot tub

Cosy cabin with hot tub in peaceful location

The Annexe with Hot Tub Virgin TV, Sky & BT Sport

Cosy cabin in Annie’s meadow

Rivermead Hut Retreat

Boxwood, Owslebury, Winchester
Family- and pet-friendly home rentals

Nettlebed Farm Holiday Lets, Barn1 of 3

The Nest

The Annexe @ Mandalay Lodge

Self-contained Garden Cottage in idyllic location

Woodrest Cabin, South Downs National Park

Coach House Flat in South Downs National Park.

Studio in Abbots Worthy

Two bedroom rural retreat.
Family-friendly home rentals with a pool

Sandy Balls Holiday Village New Forest Hampshire

Panoramic Sea Views, quiet, relaxed, cliffs, Beach

Chic Bungalow Retreat - Serene Garden, Pool & Spa

Rural Isle of Wight cottage with woodburner

The Pool House: Contemporary country escape

The Lodge

Delightful Chalet Bungalow with a Spa

Comfortable 1-Bedroom Guest Suite in rural setting
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $289 NZD | $283 NZD | $300 NZD | $331 NZD | $340 NZD | $343 NZD | $359 NZD | $362 NZD | $352 NZD | $335 NZD | $319 NZD | $328 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 |
Quick stats about holiday rentals that are family-friendly in Winchester

Total holiday rentals
Explore 1,040 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $35 NZD per night before taxes and fees

Verified guest reviews
Over 37,570 verified reviews to help you choose

Pet-friendly accommodation
Find 340 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
520 properties have a dedicated workspace

Wi-Fi availability
1,000 of Winchester holiday rentals include Wi-Fi access

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

4.7 Average rating
Winchester stays receive an average rating of 4.7 out of 5 from guests
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- New Forest National Park
- Paultons Park Home of Peppa Pig World
- University of Oxford
- Goodwood Motor Circuit
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Boscombe Beach
- Highclere Castle
- Winchester Cathedral
- Twickenham Stadium
- Chessington World of Adventures Resort
- Kimmeridge Bay
- Thorpe Park Resort
- Bournemouth Beach
- Goodwood Racecourse
- Highcliffe Beach
- Worthing Pier
- West Wittering Beach
- The Tank Museum
- Wentworth Golf Club
- Southbourne Beach
- RHS Garden Wisley
- Poole Quay
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