House holiday rentals in Winchester

Find and book unique houses on Airbnb

Top-rated house rentals in Winchester

Guests agree: these houses are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Superhost
A spacious lounge area showcases large glass windows that provide a view of the surrounding greenery. A comfortable black leather sofa is accompanied by light grey armchairs and a simple coffee table. Natural light floods the space, enhancing the warm wooden accents throughout.
Home in Hampshire
4.84 out of 5 average rating, 420 reviews

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.

Top guest favourite
An outdoor patio area is visible, featuring a dining table surrounded by eight chairs. A large umbrella provides shade. The barn's rustic wooden exterior contrasts with the neatly laid stone tiles. Lush greenery and trees form a backdrop, under a partly cloudy sky.
Home in Whiteparish
4.99 out of 5 average rating, 352 reviews

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) .

Top guest favourite
A flint-built hideaway is shown, featuring arched windows and a slate roof. The private garden is surrounded by lush green grass, with a small outdoor table and chairs visible. A tree partially frames the scene, adding to the peaceful atmosphere.
Home in Meonstoke
5 out of 5 average rating, 187 reviews

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.

Guest favourite
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
4.94 out of 5 average rating, 382 reviews

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

Top guest favourite
A modern brick exterior presents a spacious home with multiple large windows, providing ample natural light. The entrance features a covered porch, while a gravel driveway leads to the entrance. A separate structure is visible, hinting at added functionality to the property.
Home in Headbourne Worthy
4.98 out of 5 average rating, 104 reviews

Annex for couple or solo stay.

The Beehive, is a separate building with private access. It's part of our home in Headbourne Worthy and set in a peaceful semi-rural retreat. It is perfect for solo visitors or couples but not suitable for young children. We have lovely views, with great access to the rural footpaths and only a 15-20 minute walk to Winchester. It is a bright and airy space, with modern features and neutral décor. We are a 5 minute drive from the City of Winchester and mainline train station to London.

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
4.96 out of 5 average rating, 720 reviews

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.

Top guest favourite
A modern cottage exterior is surrounded by lush gardens featuring various flowering plants. The building showcases a mix of wood paneling and large windows, reflecting natural sunlight. A spacious patio area can be seen, providing an inviting space to enjoy the peaceful outdoor setting.
Home in Hampshire
4.98 out of 5 average rating, 106 reviews

Stable Cottage Beauworth Southdowns Hampshire

Welcome to Stable Cottage, your idyllic getaway. Our newly built cottage is designed to the highest standard for your comfort and enjoyment. The cozy atmosphere is enhanced by super-insulated walls and a log-burning stove that keep you warm during colder months. In summer, the sliding patio doors let in sunshine and stunning views of the Hampshire countryside. Stay connected with super-fast fibre broadband and a Smart TV. Your stay at Stable Cottage will be unforgettable.

Guest favourite
A charming garden stretches across the landscape, featuring lush greenery and a serene waterway. Two distinctive structures are visible: a traditional house and a converted mill, both surrounded by trees, creating a peaceful atmosphere by the River Meon.
Home in Hampshire
4.96 out of 5 average rating, 260 reviews

Romantic 17th Century Paper Mill on The Meon River

Enchanting converted 17th Century Paper Mill over the River Meon in Warnford, Hampshire. Quirky interior with original Japanese features. Trout anglers will have a ball. There are swans, herons, kingfishers and mallards and, if you're really lucky, you might see an otter. As you can see from the photo, the Mill is just by our cottage, but we're not always there so often you'd have the whole garden to yourself. My place is good for couples and solo adventurers.

Top guest favourite
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
4.98 out of 5 average rating, 106 reviews

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.

Guest favourite
A charming detached property is surrounded by lush greenery, featuring a gravel driveway. The two-storey building includes a wooden balcony and a staircase leading to the upper level. Planters and trees add to the serene setting, enhancing the appeal of the outdoor space.
Home in Crawley
4.97 out of 5 average rating, 336 reviews

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.

Superhost
The spacious bedroom features a wood-paneled accent wall and a large bed with light bedding and decorative pillows. A piece of wall art is displayed above the bed. Natural light enters through large windows adorned with floral curtains, providing a serene ambiance.
Home in Kings Worthy
4.78 out of 5 average rating, 210 reviews

The Granary Annex at Worthy Barn.

Ideal location for visiting the beautiful & historic Winchester in Hampshire. The Granary is 2 miles from Winchester, opposite a farm shop & lovely country pub is a 10 minute walk away. The main bedroom has a kingsize bed and views across watercress beds, the adjoining bedroom has bunk beds. The Granary is self contained with private 24 hour, access via key safe. There are many local walks and a variety of local food delivery options available.

Top guest favourite
The balcony view reveals a lush, green landscape with trees bordering a tranquil river. Fields stretch into the distance, while a well-maintained garden is visible below, featuring plants and garden structures, all bathed in soft natural light.
Home in Winchester
4.99 out of 5 average rating, 336 reviews

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.

Popular amenities for house rentals in Winchester

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$205 SGD$233 SGD$222 SGD$232 SGD$225 SGD$218 SGD$228 SGD$290 SGD$274 SGD$258 SGD$242 SGD$255 SGD
Avg. temp5°C5°C7°C9°C12°C15°C17°C17°C15°C11°C8°C5°C

Quick stats about house rentals in Winchester

  • Total holiday rentals

    Explore 130 holiday rentals in Winchester

  • Nightly prices starting at

    Winchester holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 6,410 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    130 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!

  1. Airbnb
  2. United Kingdom
  3. England
  4. Hampshire
  5. Winchester
  6. House rentals