Family-friendly vacation rentals in Winchester

4.96 out of 5 average rating, 185 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.

4.92 out of 5 average rating, 156 reviews

A well-appointed room features a spacious bed with plush bedding. Light wood flooring complements the seating area with a circular table and two upholstered chairs. Skylights and decorative lamps provide soft lighting. A mirror adds depth, and a hairdryer is available on the wall.

Guesthouse in Winchester

Central, Quiet & Self-Contained

Incredibly central location. Only 150m from Cathedral & 200m to High St. Quiet: Set back from the street, double glazing, detached building. King size bed with luxury mattress & topper, hypoallergenic duvet & pillows, Egyptian cotton bedlinen and fluffy towels. Work space. Reading & soft lighting. Well Equipped: Tea & Coffee Facilities, Mini Fridge, TV (Netflix only) Iron+Board, Hairdryer, Toiletries & Fan. Secure parking subject to availability £20per night. NB. Access via external staircase.

4.85 out of 5 average rating, 164 reviews

An open living area features a large grey sofa adorned with colorful cushions, complemented by a vibrant floral area rug. A dining table with wooden chairs sits adjacent to a modern kitchen, illuminated by soft ceiling lights.

Townhouse in Winchester

The Winchester Pad

The Winchester Pad is a spacious, modern townhouse ideally located within walking distance to the city centre and rail station to London. There is good road access in/out of the city and two free car parking permits are provided. Guests love it; with genuine accommodation all to themselves for 8 guests in 4 bedrooms and all the facilities required for an enjoyable stay. We welcome families, couples or 'professionals' from around the world seeking accommodation in this friendly, bustling city.

4.92 out of 5 average rating, 330 reviews

Apartment 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.

4.85 out of 5 average rating, 457 reviews

Home in Winchester

Bay Tree, fabulous, modern 4 bed house, Winchester

Bay Tree is a spacious house in a quiet semi-rural location close to Winchester. Please do not book for a party or loud gathering. There are four bedrooms (six beds) two with ensuites, a downstairs shower wet room, well equipped kitchen, separate utility room and a large lounge/diner. The house has an enclosed private garden with decking & bbq. There is a trampoline for children to play on in the next garden. Towels and linen provided for guest use. On drive parking for two standard cars.

Guest suite in Winchester

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.

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.

4.97 out of 5 average rating, 459 reviews

4.99 out of 5 average rating, 177 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 Winchester

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.

5.0 out of 5 average rating, 109 reviews

A polished silver bowl filled with ice displays several bottles of champagne. Fresh lilies and elegant candelabras are positioned nearby, adding a touch of sophistication to the setting. The arrangement creates a celebratory atmosphere.

Apartment in Winchester

The Sky Penthouse, City Centre Luxury

Positioned right in the heart of charming historic Winchester The Sky Penthouse offers luxury modern comfortable 5 star accommodation . Private parking for one car . Positioned an easy level 300 meter walk from the main High Street within the City Centre , 400 meters from Winchester Cathedral and 500 meters from Winchester train station. Great location with a garden. Guests can choose the bed configuration of both the double bedrooms, either 6ft wide super king luxury beds or single beds.

4.95 out of 5 average rating, 771 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 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.

4.97 out of 5 average rating, 596 reviews

A charming brick and flint building is surrounded by neatly trimmed bushes and a well-maintained garden. Two wooden chairs and a small table are set outside, inviting guests to enjoy the tranquil rural setting under clear skies.

Guesthouse in Winchester

Idyllic Hideaway Ham Green Cottage near Winchester

The Orchard Studio at Ham Green Cottage is a pretty brick and flint building tucked away in a corner of our truly English country garden. You are completely private. We are family-friendly and you can expect a comfortable stay and warm welcome. We are in a village close to the historic city of Winchester, however our setting is completely rural and quiet. We have a fantastic village pub or there are lots of places to chose from in Winchester itself - the best of both worlds!

4.95 out of 5 average rating, 424 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.

4.92 out of 5 average rating, 258 reviews

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.

Condo 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.

Popular amenities for Winchester family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Cottage in Sutton Scotney

Ultra luxury, newly refurbished country retreat

4.88 out of 5 average rating, 510 reviews

4.9 out of 5 average rating, 105 reviews

A private deck features a luxurious hot tub surrounded by lush greenery. A round glass table with six cushioned chairs offers a space for dining or relaxation. A neatly folded towel is placed on the deck, enhancing the inviting outdoor setting.

Chalet in Pitt

Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB

4.89 out of 5 average rating, 292 reviews

Home in Bosham

Cedar House - Pool & Spa Complex

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.

A Unique Farm Retreat

4.96 out of 5 average rating, 381 reviews

4.97 out of 5 average rating, 232 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

4.91 out of 5 average rating, 201 reviews

The exterior of a luxury period property is showcased, featuring a large garden area with lush green grass. The house displays a blend of brick and greenery, including a charming conservatory with numerous windows. Trees frame the property, enhancing the serene outdoor setting.

Home in Hampshire

A holiday home in New Forest with pool & hot tub

4.86 out of 5 average rating, 299 reviews

Home in Owslebury

The Joinery, Owslebury, Winchester

4.99 out of 5 average rating, 242 reviews

A cozy lounge area features a teal sofa, beanbag, and a rustic wooden coffee table. A brick fireplace with a log burner adds warmth, while a dining table is positioned nearby. A ladder leads to a mezzanine sleeping space, decorated with fairy lights.

Farm stay in Cadnam

A cosy farm cottage, with lots of character.

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 410 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

4.96 out of 5 average rating, 563 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

4.82 out of 5 average rating, 160 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

4.95 out of 5 average rating, 149 reviews

A charming wooden annexe is nestled within a lush green garden, surrounded by manicured bushes. The building features a light-colored door and window shutters, adding to the rustic aesthetic. A small patio area with seating is visible, inviting outdoor relaxation.

Bungalow in Hampshire

The Annexe - Unique and Tranquil Getaway.

4.96 out of 5 average rating, 286 reviews

A spacious apartment complex is surrounded by lush greenery and trees, with well-maintained gardens showcasing a neat arrangement of colorful flowers. A paved driveway leads to the entrance, providing access to the residences, amidst a tranquil countryside setting.

Guesthouse in Hawkley

Daily Red Kite Feed & Pool - Countryside Apartment

4.94 out of 5 average rating, 196 reviews

The sitting room features high ceilings with exposed wooden beams and large skylights providing ample natural light. Comfortable seating arrangements include a blue couch and a cream sofa, complemented by a small wooden table. A bookshelf filled with books and a small television are visible along one wall.

Guest suite in Houghton

Peaceful barn conversion in rural location.

4.97 out of 5 average rating, 366 reviews

The exterior of Colindale Cottage is depicted, showcasing a two-story structure with a light-colored façade. A garden room with glass panels is visible, along with well-kept flowerbeds and a lush green lawn. A large tree provides shade in the tranquil outdoor space.

Cottage in Hampshire

Colindale Cottage, Nether Wallop

4.98 out of 5 average rating, 149 reviews

The Watch House is viewed from a garden path lined with blooming flowers, leading down to the beach. The white exterior of the cottage is highlighted against a clear blue sky, while the tide is low, revealing a sandy shore.

Home in Lepe

Iconic Beach Front Stay | The Watch House, Lepe

Family-friendly home rentals with a pool

Place to stay in Hill Brow

A modern guest lodge is showcased, featuring a distinctive curved roof and large glass windows that enhance the natural light. The surrounding outdoor area is paved, including a pool with a cover and seating arrangements for relaxation.

The Pool House (for 2 Adults & 2 Children)

4.99 out of 5 average rating, 118 reviews

4.98 out of 5 average rating, 360 reviews

Guesthouse in Grayswood

Grayswood Cowshed in stunning Grounds

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.

Sandy Balls Holiday Village New Forest Hampshire

4.99 out of 5 average rating, 216 reviews

4.98 out of 5 average rating, 105 reviews

An indoor heated swimming pool is set against a backdrop of wooden beams and natural light streaming through large windows. The clear blue water is bordered by tiled flooring, and a stained glass window adds a colorful accent to the serene environment.

Cottage in Lyndhurst

Charming cottage with pool in the New Forest

4.88 out of 5 average rating, 116 reviews

Cottage in Steep

Secluded Country Cottage

4.88 out of 5 average rating, 154 reviews

A renovated barn exterior is framed by a charming garden with purple flowers. The entrance features a covered porch and large glass doors, leading to an inviting seating area with wicker furniture arranged around a table.

Farm stay in Plaitford

Cottage Pye - Beautiful Barn In The New Forest

Guesthouse in West Sussex

A spacious bedroom features a comfortable bed dressed in light bedding. Large windows allow natural light to fill the room, with views of greenery outside. Artwork adorns the walls, and a cozy sitting area includes a chair and a television, enhancing the room's inviting atmosphere.

Comfortable 1-Bedroom Guest Suite in rural setting

4.96 out of 5 average rating, 189 reviews