House holiday rentals in Winchester

The Joinery, Owslebury, Winchester

The Joinery is on the edge of Owslebury, a picturesque village just south of Winchester. It is light and airy and offers 4 bedrooms on ground floor level, two with ensuite shower and a family bathroom. Upstairs is a large open plan area with kitchen, dining table and sofas for relaxing and enjoying the views of the surrounding countryside.There is also a snug room with TV. There are steps down to the main entrance so not suitable for people with mobility issues. The garden area is not enclosed.

Location · Value · Pets

The Garden Wing is a very special tranquil place

This unique place has a style all its own. Designed in a Japanese way with it's own Water Garden, terrace and boardwalk. Ideal for a family and children will love The Garden Wing, but there is access to the Japanese water garden, and bedroom 3+4 have unguarded stairs to unuseable mezzanine bunks ( see photos). If in any doubt about suitability.....please message me before booking. It is perfect for 6 people, but has beds for 8 EV charger. Oct-Mar + Midweek availability message me first please

Value · Family · Check-in

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.

Family · Location · Getting around

The Summer House

The Summer House is a recently converted guest house, self contained with fully equipped kitchen , beautifully fitted bathroom ,double bed on the galleried mezzanine level ,accessed by ladder stairs with vaulted ceiling creating a loft style. It is fully heated ,has wi-fi , streamed TV, and ceiling speakers for streaming music. The space is modern,bright ,yet cosy. Outdoors it sits at the top of 14 acres of grounds over looking the main house. There is a private entrance and parking on site.

Family · Value · Decor

Stride’s Barn

A newly restored and beautifully refurbished oak framed barn conversion bordering the New Forest National Park . With spectacular far reaching views Stride’s Barn is situated 9 miles from the Cathedral City of Salisbury and 15 miles from Southampton . An ideal base to explore the local areas including many walks, pubs , restaurants, golf clubs and other tourist attractions such as Stonehenge and Paultons Park/Peppa Pig World . Can be rented with additional listing ‘The Cowshed’ (sleeps 2) .

Family · Location · Hospitality

4 Bed City House with Private Garden and Parking

Discover our beautifully decorated four-bedroom home in Winchester's historic city centre. Enjoy the convenience of two rare parking spaces and a courtyard garden to unwind in. Indulge in the city's amenities that are just a stone's throw away, from artisan coffee shops to chic restaurants. Winchester Cathedral is only a leisurely five-minute stroll away! Whether for leisure or business, our spacious home offers comfort and convenience. Experience Winchester's charm and book your stay today!

Location · Family · Indoor spaces

The Piggery: with tennis court and games barn

The Piggery is a secluded flint built hideaway, with lots of period charm, set in the grounds of a manor house. Converted to a high standard it has it’s own private garden, access to the owners tennis court & a large barn with table tennis, table football & pool, wider house grounds including an island, surrounded by the river Meon. Numerous walks direct from The Piggery and a number of local vineyards are nearby. 5/10mins walk away are two super pubs and the very well stocked village shop.

Location · Family · Heating

Oak Framed Barn with Tennis Court

A stylish secluded, two storey, oak framed barn with tennis court, 4 miles from Winchester. Homely space with two bedrooms plus a sofa bed (upon request) and ground floor open plan living area. Super fast WiFi. The Barn adjoins the Watercress Way and stands separately in the grounds with views over open Hampshire fields. Nearest neighbour c.1 mile away but there is loads to do in the area with an abundance of country pubs, one or two within walking distance and beaches within 50 minutes

Value · Family · River

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.

Location · Family · Nearby

Iconic Beach Front Stay | The Watch House, Lepe

A standout seafront landmark on Lepe Beach, The Watch House is a lovingly restored former lifeboat and coastguard station, once used to combat smuggling across the Solent. With original features, a modern kitchen, wood burner, cosy window seat over the water, and views to the Isle of Wight, it’s a guest favourite—“an iconic beachfront stay” and “perfect relaxing getaway.” Pet-friendly with parking for two, perfect for families, couples, or friends.

Value · Family · Quiet

Secluded and peaceful home in beautiful village

A delightful detached two storey property in the grounds of Whitethorn cottage, in the picturesque village of Crawley near the historic city of Winchester. Secluded and quiet with pleasant garden views. Nicely furnished to a high standard throughout. Crawley is a beautiful classic English village with an excellent gastro pub, within easy walking distance. We will be available to offer help and advice on the many places to visit in the local area.

Family · Value · Check-in

Martyr Worthy Home with a View

Situated at the end of a lane with the river as your neighbour, the accommodation is set in beautiful cottage gardens. With walks on your doorstep and local village pubs just a stroll across the fields, you have the benefit of a peaceful rural location and the convenience of being close to the historic city of Winchester and the attractive Georgian town of Alresford.

Location · Value · Kitchen