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.

%{current} / %{total}1 / 1
Top Guest favourite
The bungalow's exterior features a combination of brick and wood with a textured gabled roof. Flower pots and beds with colorful blooms line the pathway, leading to large windows that allow natural light into the interior.
Bungalow in Eastleigh
4.93 out of 5 average rating, 410 reviews

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.

Top Guest favourite
Two distinct entrances are visible, each framed by elegant archways. A decorative black iron railing separates the front door area from the sidewalk, while light green planters with small shrubs add a touch of greenery to the scene. Large windows allow natural light to fill the interior.
Guest suite in Hampshire
4.97 out of 5 average rating, 408 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.

Top Guest favourite
A cozy bedroom features a gray headboard with two twin beds, adorned with decorative pillows depicting trees. Fresh towels are neatly arranged at the foot of the beds. Natural light enters through a skylight, illuminating the soft green walls, while a hallway leads to the lounge area.
Guest suite in Chandler's Ford
4.89 out of 5 average rating, 540 reviews

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.

Top Guest favourite
The bedroom features a spacious bed dressed in soft grey bedding, complemented by decorative cushions. Light streams through the window, softened by sheer curtains. A bedside table with literature adds a functional touch, while a wall-mounted mirror enhances the overall brightness.
Home in Hampshire
4.96 out of 5 average rating, 715 reviews

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.

Guest favourite
A cozy studio bedroom features a spacious bed with white linens and a decorative pillow. Bedside tables with lamps flank each side of the bed. Light wood flooring complements the natural light from the window, while a green plant adds a touch of nature to the space.
Farm stay in Hampshire
4.91 out of 5 average rating, 339 reviews

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.

Top Guest favourite
The lounge area features a comfortable sofa adorned with colorful cushions and a light rug underfoot. A small armchair adds seating options, while natural light filters through the large windows, illuminating the room. A round coffee table rests in the center, enhancing the cozy atmosphere.
Apartment in Winchester
4.95 out of 5 average rating, 367 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.

Guest favourite
A private entrance is visible, framed by lush greenery and colorful flowers. The brick exterior features a window that allows light to illuminate the space inside. A stone pathway leads to the entrance, adding to the inviting feel of the small garden.
Guest suite in Hampshire
4.86 out of 5 average rating, 475 reviews

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.

Top Guest favourite
A gray sofa is positioned against a white wall, accompanied by decorative pillows. Two side tables with lamps flank the sofa. Light wooden flooring extends throughout the room, and a yellow area rug adds warmth. A door leads to an outdoor area on the left.
Guest suite in Warsash
4.99 out of 5 average rating, 160 reviews

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.

Top Guest favourite
A modern studio layout is displayed, featuring a kitchenette with a microwave, oven, and fridge. Bright yellow accents enhance the design. A small dining area with two barstools is positioned near a flat-screen TV. Natural light fills the space through a window with a light-filtering blind.
Guest suite in Hampshire
4.97 out of 5 average rating, 188 reviews

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!

Top Guest favourite
A modern living space is visible through open bi-fold doors, blending indoor and outdoor areas. A sleek seating arrangement is placed outside on a patio, complemented by soft lighting. Inside, a light-filled room showcases a comfortable sofa and dining area, enhancing the welcoming atmosphere.
Tiny home in Winchester
4.95 out of 5 average rating, 234 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

Top Guest favourite
The living room features a light and airy design, showcasing a two-seater sofa and a separate sofa bed. A dining table for four is centered in the space, complemented by a fireplace and a wall-mounted TV. Decorative plants enhance the welcoming atmosphere.
Apartment in Hampshire
4.93 out of 5 average rating, 192 reviews

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.

Top Guest favourite
A spacious room features a king-size sofa bed dressed in a colorful duvet cover. Two skylights provide natural light, and a desk with a computer chair is set nearby. A small white side table adds functionality to the space.
Guest suite in Chandler's Ford
4.95 out of 5 average rating, 150 reviews

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

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$295 AUD$339 AUD$322 AUD$363 AUD$398 AUD$394 AUD$379 AUD$430 AUD$389 AUD$354 AUD$358 AUD$358 AUD
Avg. temp5°C5°C7°C9°C12°C15°C17°C17°C15°C11°C8°C5°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 $90 AUD per night before taxes and fees

  • Verified guest reviews

    Over 6,690 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    150 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!