Family-friendly holiday rentals in Winchester

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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
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, 395 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 quiet street is lined with period houses, showcasing a mix of red brick and white facades. The cobblestone pavement leads past quaint buildings, with clear blue skies overhead. Architectural details include shuttered windows and gabled roofs, creating a charming urban atmosphere.
Townhouse in Hampshire
4.99 out of 5 average rating, 141 reviews

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.

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, 536 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
4.95 out of 5 average rating, 706 reviews

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.

Guest favourite
The studio features an elegantly decorated sleeping area with a spacious bed adorned with a colorful bedding. Soft lighting highlights the intricate mirror and chandelier. A comfortable chair sits beside the bed, while large curtains frame the windows, adding to the cozy ambiance.
Apartment in Hampshire
4.92 out of 5 average rating, 185 reviews

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 ✅

Guest favourite
A spacious studio annex features a king-size bed with a light blanket, a comfortable sofa, and a wooden coffee table. Natural light enters through a window, highlighting the simple white walls and wooden flooring. A dresser and rack add functional decor to the room.
Guest suite in Ovington
4.97 out of 5 average rating, 161 reviews

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.

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
4.92 out of 5 average rating, 330 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.
Flat in Winchester
4.95 out of 5 average rating, 358 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, 470 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, 158 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, 185 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!

Guest favourite
A charming black wooden structure features white paneled doors and windows. A small potted tree is positioned near the entrance, while gravel creates a neat pathway leading to the door. Surrounding greenery adds a touch of nature to the setting.
Guest suite in Winchester
4.9 out of 5 average rating, 183 reviews

Beautiful guest suite in rural Hampshire

Set in the grounds of a Grade II listed thatched cottage on the edge of Kings Worthy village, our annex is beautifully decorated and comfortable. With its own entrance and small private outdoor area, this property combines rural charm and handy local amenities (bus stop just outside to central Winchester and fantastic local pub just a two minute walk away). Tea and coffee are provided as well as breakfast cereals, bread/butter and fruit jams.

Popular amenities for Winchester family-friendly rentals

When is the best time to visit Winchester?

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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
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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!