Family-friendly holiday rentals in Winchester

4.97 out of 5 average rating, 135 reviews

A light-filled living area features a comfortable gray sofa adorned with patterned cushions. A small, cozy armchair sits nearby, and a wooden coffee table is positioned in front. Natural light streams through the window, highlighting a light blue wall and decorative shelf.

Condo in Winchester

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.

4.93 out of 5 average rating, 408 reviews

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

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.

4.96 out of 5 average rating, 193 reviews

A bright and spacious sleeping area features a king size bed adorned with decorative pillows. Natural light enters through a skylight and side window. A wooden wardrobe and a small television provide functional storage and entertainment options. The area is carpeted for comfort.

Guest suite in Hampshire

The Queen Bee with off road parking

A peaceful and self contained home situated in a cul-de sac, conveniently located just 23 mins walk from central Winchester or 7 mins walk to bus stop ( every 15mins). Local amenities include Waitrose, pharmacy, wide range of restaurants/take away. Pub offering food within 15 mins walk or country pubs within 10 mins drive. On site parking, outside area with BBQ for alfresco dining. This is a newly furnished property with a king size bed upstairs, bed settee, kitchen area, bathroom with shower.

4.99 out of 5 average rating, 141 reviews

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

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.

Guest suite in Chandler's Ford

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.

4.89 out of 5 average rating, 535 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.

4.95 out of 5 average rating, 705 reviews

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

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.

4.92 out of 5 average rating, 184 reviews

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.

Condo in Hampshire

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 ✅

4.97 out of 5 average rating, 161 reviews

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

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.

4.91 out of 5 average rating, 328 reviews

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.

4.95 out of 5 average rating, 356 reviews

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

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.

4.86 out of 5 average rating, 468 reviews

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

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.

4.95 out of 5 average rating, 220 reviews

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

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

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Place to stay in Bursledon

A serene view of the river Hamble is captured, featuring several sailboats anchored in the water. Lush green trees line the background, complementing the peaceful river setting. Sunlight glistens off the boats, enhancing the tranquil atmosphere of the natural landscape.

4.92 out of 5 average rating, 301 reviews

Hacketts Annex, HotTub, Old Bursledon Hamble River

4.98 out of 5 average rating, 121 reviews

A vibrant garden borders the side of the annexe, featuring colorful flowers in various hues, including pink, yellow, and white. This lush area is complemented by a gravel pathway and the wooden exterior of the annexe, creating a welcoming outdoor setting.

Cottage in Denmead

Adorable Detached 1 bedroom Annexe with hot tub

4.87 out of 5 average rating, 263 reviews

The exterior of The Joinery reveals a modern two-story structure with a combination of brick and wood accents. Large glass doors open to a private terrace area surrounded by greenery. The property is framed by fencing and features a gravel pathway leading to the entrance.

Home in Owslebury

The Joinery, Owslebury, Winchester

4.87 out of 5 average rating, 465 reviews

A spacious bedroom is furnished with a kingsize bed adorned with a floral-patterned duvet cover and decorative pillows. Large, dark blinds cover the window, while a piece of wall art featuring flowers is displayed above the bed. The en-suite bathroom is partially visible in the background.

Guest suite in Hedge End

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

Guesthouse in Southampton

The exterior of the cabin is painted in soft green tones, featuring large double doors with decorative lace curtains. Flowering plants are positioned beside the entrance, while a lattice screen adds privacy. A small seating area with a glass table is visible in front.

4.96 out of 5 average rating, 847 reviews

Cosy cabin with hot tub in peaceful location

4.9 out of 5 average rating, 275 reviews

Tiny home in West Meon

Cosy cabin in Annie’s meadow

Shepherd’s hut in Hampshire

The exterior of a charming shepherd's hut is showcased, featuring a wooden facade with large windows and a welcoming front door. A small patio area with two black wicker chairs and a glass table is set against a landscaped garden, surrounded by greenery and blooming flowers.

4.93 out of 5 average rating, 405 reviews

Rivermead Hut Retreat

Farm stay in Headbourne Worthy

A rustic cabin with a dark metal roof and timber exterior is surrounded by trees. Smoke gently rises from a chimney. The front porch, featuring large glass doors, leads to a welcoming seating area. A pathway of stepping stones guides the way through the lawn.

4.98 out of 5 average rating, 339 reviews

A Unique Farm Retreat

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 531 reviews

A wooden deck area is visible, featuring a small dining table and chairs. A bicycle wheel leans against the wall, while colorful foliage frames the space. The interior is partially visible, showcasing a bright and airy atmosphere with shelves and a dining area.

Guesthouse in Sparsholt

The Hayloft - Rural retreat very near Winchester

4.98 out of 5 average rating, 368 reviews

Three cabins are arranged in a peaceful setting surrounded by greenery. A stone pathway leads to the front of the cabins, marked by wooden posts. Large windows provide views of the exterior landscape, creating a harmonious connection with nature.

Barn in Durley

Nettlebed Farm Holiday Lets, Barn1 of 3

4.94 out of 5 average rating, 376 reviews

A rustic oak-framed barn is nestled among trees, showcasing a sloped roof and large windows. Gravel pathways lead to the entrance, framed by potted plants. The structure is surrounded by open space, offering a serene rural setting.

Home in Winchester

Oak Framed Barn with Tennis Court

4.83 out of 5 average rating, 145 reviews

An open plan living, kitchen, and dining area is depicted, featuring a dining table with wooden chairs and a patterned tablecloth. The kitchen includes a stainless steel refrigerator, stove, and ample cabinetry. Soft seating is arranged in the living area, enhancing a comfortable environment.

Cottage in Shawford

The Nest

4.91 out of 5 average rating, 144 reviews

A cozy living area features a light grey sofa positioned to face a television displaying Netflix. A modern wood-burning stove adds warmth to the space, while a door with multiple glass panels leads outside. Light hardwood flooring completes the inviting atmosphere.

Apartment in Medstead

The Annexe @ Mandalay Lodge

4.96 out of 5 average rating, 313 reviews

The exterior of Garden Cottage is framed by a well-tended garden featuring flowering plants and a manicured hedge. A paved pathway leads to a cozy seating area, and large windows reflect the natural surroundings. A welcoming atmosphere is established by the combination of greenery and rustic wooden structure.

Tiny home in Soberton

Self-contained Garden Cottage in idyllic location

Apartment in New Alresford

A spacious bedroom features a wooden bed frame with a light-colored bedspread. Soft lighting is provided by a bedside lamp and a decorative ceiling light. Light-colored curtains frame the window, allowing natural light to fill the room. Artwork adorns the walls, adding to the decor.

4.93 out of 5 average rating, 167 reviews

Stunning apartment in the heart of New Alresford

Guest suite in Abbots Worthy

The studio features a spacious super-king bed adorned with decorative cushions and a cozy throw. A well-equipped kitchenette and dining area are visible, alongside fitted cabinets that offer storage. Soft lighting enhances the calming color palette, creating a cozy and functional space.

4.96 out of 5 average rating, 107 reviews

Studio in Abbots Worthy

Family-friendly home rentals with a pool

Holiday park in Hampshire

A large heart-shaped sculpture is positioned on a circular wooden platform, surrounded by natural vegetation. The backdrop features rolling hills under a sky with varying cloud coverage, enhancing the scenic view of the surrounding landscape.

4.99 out of 5 average rating, 171 reviews

Sandy Balls Holiday Village New Forest Hampshire

Shepherd’s hut in Ashley Heath

A rustic Acorn Hut, clad in green, is surrounded by lush foliage and blooming flowers. A hot tub sits on a wooden deck, while a wood burner is positioned nearby, enhancing the natural setting. The entrance to the hut is inviting, framed by greenery.

4.96 out of 5 average rating, 414 reviews

Cosy Shepherd's Hut with wood-fired hot tub

4.88 out of 5 average rating, 161 reviews

An indoor pool area is framed by large glass doors, allowing natural light to enhance the space. The pool features a vibrant blue color, surrounded by stylish loungers and illuminated by soft mood lighting. A spa area with textured tiles is visible at the far end.

Bungalow in Bosham

Chic Bungalow Retreat - Serene Garden, Pool & Spa

4.86 out of 5 average rating, 195 reviews

A blue wooden table with matching chairs is arranged on a patio overlooking expansive views of the Solent. The grass area beyond leads to the waters, framed by scattered chalets in the distance under a cloudy sky.

Bungalow in Warsash

Sea Views, Seaside, Quiet,Relaxing, Beach,Cliffs,

4.96 out of 5 average rating, 194 reviews

An outdoor space features a hot tub in the foreground, with jets gently bubbling. A swimming pool is visible in the background, surrounded by a stone patio and outdoor furniture. Lush greenery and a sunset sky create a serene backdrop.

Place to stay in Stroud

The Pool House: Contemporary country escape

4.97 out of 5 average rating, 180 reviews

A beach hut style home features a charming exterior with a blue front door and three symmetrical gabled sections. Surrounding greenery adds a natural touch, while a tennis court in the foreground provides an outdoor recreational space.

Bungalow in Oving

The Beach Huts: with tennis court & seasonal pool

4.98 out of 5 average rating, 105 reviews

The image showcases the exterior of a two-bedroom bungalow, featuring a sloped roof and a combination of white and brown siding. A gravel driveway is visible, secured by a wooden gate with metal hardware, leading to an open area surrounded by greenery.

Home in Hampshire

Eden Cottage, your home away