
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.

One bedroom home.
Relax and make yourself at home in this comfortable bungalow with sunny lounge, fully equiped kitchen/diner and bathroom. Situated in a quiet cul-de-sac in the village of Bishopstoke on the outskirts of Eastleigh. The M27 and M3 motorways and Southampton Airport are just a few miles away. The historic City of Winchester is an easy drive. Whether you are on your way to explore the South West, visiting family or friends or just wanting a short break, we offer a convenient home away from home.

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.

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.

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.

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.

The Warsash Annex
The unit is a completely self-contained extension of the existing property. It is has been recently built to a high specification, including a very comfy bed. It is located in the heart of Warsash village, walking distance from all amenities. It is ideally suited for a very comfortable, short stay. Wifi is included as are all utility bills. There is a lot of storage space and a private entrance from the driveway where there is space for 1 car to park.

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

Modern Apartment Central Winchester
Situated in the heart of Winchester, this newly refurbished 2-bedroom apartment with its own private entrance and modern décor provides a well thought out space for friends, couples & families. This cosy home provides an excellent upmarket base to explore Winchester. A stone’s throw to the city’s favourite pub, St James Tavern, a warm welcoming traditional pub which serves excellent locally sourced home cooked food.

Private detached en-suite annexe
Private detached en-suite room above the garage of our family home in a peaceful, leafy community. Accessed by its own door, behind a locked garden gate. Self check in available via key safe. Ideally placed close to the M3 (2 miles) with easy access to Romsey, Winchester, Southampton (including the airport and cruise terminals), New Forest and many more great localities.
Popular amenities for Winchester family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Studio with Hot Tub & Sauna

Sandy Balls Holiday Village New Forest Hampshire

Oak Tree Retreat

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

Hacketts East Wing HotTub Bursledon Hamble River

Adorable Detached 1 bedroom Annexe with hot tub

Rivermead Hut Retreat

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath
Family- and pet-friendly home rentals

Peaceful barn conversion in rural location.

The Barn @ North Lodge -Soho Farmhouse-esque Cabin

Nettlebed Farm Holiday Lets, Barn1 of 3

Pretty Garden View at Coopers Farmhouse

The Annexe @ Mandalay Lodge

Lockerley Log Cabin Guesthouse

Self-contained Garden Cottage in idyllic location

Woodrest Cabin, South Downs National Park
Family-friendly home rentals with a pool

Panoramic Sea Views, quiet, relaxed, Cozy, Beach

Beautiful S.Downs Cottage, pool and tennis

The Ndoro Carriage with use of A Natural Pool.

The Pool House: Contemporary country escape

Delightful Chalet Bungalow with a Spa

Martyr Worthy Home with a View

Country getaway on rural Surrey/Sussex border.

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 | £147 | £168 | £160 | £180 | £198 | £195 | £188 | £213 | £193 | £175 | £178 | £178 |
| 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 £44 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!
Destinations to explore
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- Family-friendly rentals Hampshire
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- Family-friendly rentals United Kingdom
- New Forest National Park
- Paultons Park Home of Peppa Pig World
- Oxford University
- Goodwood Motor Circuit
- Stonehenge
- Windsor Castle
- Hampton Court Palace
- Boscombe Beach
- Lower Mill Estate
- Highclere Castle
- Winchester Cathedral
- 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




