
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.

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.

Self Contained Apartment in Chandler’s Ford
This light and airy open plan, ground floor apartment is a newly converted, completely self-contained extension of our home and therefore provides accommodation with no household mixing. Ideal in these strange COVID times. It has a kitchen/diner lounge area, a shower room, bedroom and parking, ideally suited for a very comfortable stay where you can cater all meals for yourself. It is conveniently located mid way between Winchester and Southampton, just a few minutes from the M3/M27.

Quiet Winchester One 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 ✅

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!
Luxury annexe near the River Itchen & Alresford
Beautifully decorated studio annex in the village of Ovington - a lovely rural spot yet a short drive from Winchester and walkable to Alresford. Light and airy space - king size bed, sofa, TV, chest drawers and table & chairs. There is a small kitchenette (small fridge, kettle, toaster, microwave, cafetiere, crockery, glassware and cutlery). Fresh towels, tea, coffee and biscuits are ready for you on your arrival. An iron, cot and high chair can be arranged on request.

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.

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

Oak Tree Retreat

80 acre Wood, Dutchtub, Lake, Treehouse & Zip-line

Hacketts Annex, HotTub, Old Bursledon Hamble River

Adorable Detached 1 bedroom Annexe with hot tub

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

Cosy cabin with hot tub in peaceful location

Cottage in beautiful Hampshire village

Rivermead Hut Retreat
Family- and pet-friendly home rentals

Peaceful barn conversion in rural location.

Coach House in the heart of the test valley

Oak Framed Barn with Tennis Court

Pretty Garden View at Coopers Farmhouse

The Annexe @ Mandalay Lodge

Lockerley Log Cabin Guesthouse

Little Trout, Nether Wallop: an oasis of calm

Stunning apartment in the heart of New Alresford
Family-friendly home rentals with a pool

Panoramic Sea Views, quiet, relaxed, Cozy, Beach

Sandy Balls Holiday Village New Forest Hampshire

Cosy Shepherd's Hut with wood-fired hot tub

Chic Bungalow Retreat - Serene Garden, Pool & Spa

Rural cottage with pool at Cheverton Farm Holidays

The Pool House: Contemporary country escape

Delightful Chalet Bungalow with a Spa

Shepherd's Hut with Hot Tub near Winchester
When is the best time to visit Winchester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $259 SGD | $297 SGD | $282 SGD | $318 SGD | $349 SGD | $345 SGD | $332 SGD | $376 SGD | $341 SGD | $310 SGD | $314 SGD | $314 SGD |
| 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 150 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $78 SGD per night before taxes and fees

Verified guest reviews
Over 6,690 verified reviews to help you choose

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
150 of Winchester holiday rentals include wifi 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!
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- New Forest national park
- Goodwood Motor Circuit
- Paultons Park Home of Peppa Pig World
- Oxford University
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Bournemouth Beach
- Boscombe Beach
- Lower Mill Estate
- Winchester Cathedral
- Highclere Castle
- Chessington World of Adventures Resort
- Kimmeridge Bay
- Thorpe Park Resort
- West Wittering Beach
- Goodwood Racecourse
- Highcliffe Beach
- Southbourne Beach
- Worthing Pier
- The Tank Museum
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- RHS Garden Wisley
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