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.

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Top guest favourite

Flat in Winchester

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.

FamilyKitchenWalkability

4.92 out of 5 average rating, 331 reviews

Top guest favourite

Apartment in Winchester

Stable Apartment with Hot Tub near Winchester

Newly renovated apartment with copper bath and hot tub in a converted stable 3 miles from Winchester. The well-equipped kitchen has a dining table with banquette seating, boot room/utility, and sitting room with flame effect fire. Guests have access to the owner’s pool (May to September) for up to three hours per day, and tennis court. Private hot tub and fenced garden with outdoor furniture. Not suitable for children and infants aged 12 and younger (unfenced pond, pool, dogs on site).

FamilyIndoor spacesOutdoor spaces

4.92 out of 5 average rating, 287 reviews

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 Winchester

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.

Indoor spacesKitchenHeating

4.97 out of 5 average rating, 467 reviews

Top guest favourite

Home in Hampshire

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.

Indoor spacesKitchenHeating

4.99 out of 5 average rating, 137 reviews

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 Winchester

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.

KitchenIndoor spacesHot tub

4.95 out of 5 average rating, 779 reviews

Guest favourite

Tiny home in Winchester

Cosy rural hideaway, Hursley, near Winchester

Fantastic rural retreat! Gorgeous cosy space, very private with own secluded garden. Everything that you need for a relaxing break. Five miles from both Winchester and Romsey, a fifteen minute walk to the lovely village of Hursley with its two pubs and great walks! Perfect for IBM Hursley, Peppa Pig World/Paultons Park, the New Forest (25 minutes) and beaches (40 minutes). You can be in Southampton with cinemas, bowling, shopping etc in 20 minutes. A great exploring base!

KitchenIndoor spacesNearby

4.83 out of 5 average rating, 481 reviews

Top 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

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.

KitchenFamilyDecor

4.92 out of 5 average rating, 428 reviews

Top guest favourite

A spacious bedroom features a comfortable kingsize bed adorned with decorative pillows. On each side of the bed, bedside lamps provide soft illumination. Framed artwork is displayed on the wall above, while a vintage mirror enhances the light and openness of the space.

Guest house in Exton

The Woodshed

The Woodshed is right in the heart of the South Downs National Park, between the villages of Warnford and Exton, a secluded and peaceful space surrounded by a working farm. The Woodshed has a view of Old Winchester Hill that is magic. Activities in the area include biking, hiking, and angling, and three of the best pubs in Hampshire are within a 5 mile radius. As we are a little distance from the main track, I am happy to come and collect guests from Exton if walking.

Indoor spacesFamilyBiking

4.99 out of 5 average rating, 139 reviews

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.

Flat in Winchester

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.

Indoor spacesFamilyAccuracy

4.95 out of 5 average rating, 429 reviews

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 Winchester

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.

FamilyIndoor spacesValue

4.92 out of 5 average rating, 264 reviews

Top guest favourite

The Cottage features a charming exterior with a textured roof and a modern patio area. Surrounded by greenery, a spacious seating arrangement is set on a stone surface, offering a tranquil spot for relaxation. Nearby structures exhibit a contemporary architectural style.

Cottage in Winchester

The Cottage in Compton

Come and enjoy a stay in The Cottage, located in the grounds of our 17th Century converted Barn. Enjoy a unique location on the edge of Winchester with direct access to the countryside. The Cottage has been recently extended and refurbished with everything you will need to make your stay enjoyable. A perfect place for a break to explore all the wonderful things that Winchester has to offer!

KitchenFamilyTV

4.99 out of 5 average rating, 224 reviews

Guest favourite

A light-filled living area showcases a comfortable sofa draped with a blue blanket and decorative cushions. A small table sits beside the sofa on natural woven flooring. The bedroom is visible through sliding doors, featuring a bed with colorful linens and a window that allows for ample natural light.

Guest house in bugmore hill

Stunning oak-framed "Loft House"

The "Loft House" was built in 2017 and has been freshly decorated to create a calm and stylish space. It is situated in a truly beautiful and tranquil rural location, and is a fantastic base to explore this lovely part of Hampshire. It is a cosy compact space so ideal for a couple or two adults, and could also accommodate up to two children. It is not suitable for more than two adults.

KitchenFamilyTV

4.94 out of 5 average rating, 206 reviews