House vacation rentals in Winchester

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Top-rated house rentals in Winchester

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Top guest favorite
The newly built annex is shown from the outside, featuring a smooth exterior in soft hues and a dark slate roof. Expansive glass doors open towards the patio, allowing for natural light. Surrounded by green grass, the setting emphasizes a serene atmosphere.
Home in Nether Wallop
5 out of 5 average rating, 158 reviews

Little Gables in Nether Wallop

Welcome to our gorgeous annex in the heart of Nether Wallop! This newly built annex offers the perfect getaway for up to four friends or a family in the heart of the Test Valley. It has 2 bedrooms, a well-equipped kitchen, comfy living and dining area, and a beautiful shower room. Nestled between Salisbury and Winchester, our annex is perfectly located for exploring the charming Hampshire and Wiltshire countryside and enjoying a delightful country escape. Book now and create lasting memories!

Top guest favorite
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, 351 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 favorite
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, 185 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.

Top guest favorite
The exterior of Little Ashbrook is presented, showcasing a charming brick facade with a sloped roof. The entrance is framed by plants in decorative pots, with gravel pathways leading to the door. Large windows allow glimpses of the interior, illuminated from within.
Home in Abbotts Ann
4.99 out of 5 average rating, 189 reviews

Spacious one bedroom annex in Hampshire village

Little Ashbrook is a newly renovated annex adjacent to our main home, on the edge of the pretty Hampshire village of Abbotts Ann. Just 5 minutes walk to 2 village pubs and an excellent award-winning, well stocked village shop and post office. Conveniently located to explore Iron Age forts, Stonehenge, Avebury, the bustling market town of Stockbridge, the Cathedral cities of Winchester and Salisbury, the New Forest and the South Coast. London Waterloo is an hour by train. A perfect escape!

Guest favorite
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, 379 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 favorite
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, 103 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 favorite
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, 715 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 favorite
An open-plan kitchen area features warm wood accents, with pendant lighting hanging above the counter. Shelves display various kitchen items against a textured backsplash. A cozy seating area with a leather armchair is visible, accompanied by wooden furniture and soft lighting enhancing the inviting space.
Home in Wiltshire
4.94 out of 5 average rating, 108 reviews

The Little Forge

Enjoy a relaxing break in the heart of the beautiful Pewsey Vale. The Little Forge is set on a quiet lane at the edge of the friendly village of Pewsey, in an area of outstanding natural beauty. Enjoy countryside walks in the beautiful surroundings or explore the mystical Avebury, the market town of Marlborough or the pretty villages along the Kennet and Avon Canal. At the end of the day cozy up in front of the log burner or spend the evening in one of the local pubs or restaurants.

Top guest favorite
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, 104 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.

Top guest favorite
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, 99 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 favorite
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, 335 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.

Top guest favorite
Home in Romsey
5 out of 5 average rating, 214 reviews

John's Barn

John's Barn is an architect designed conversion of an existing barn. With 3 bedrooms, 2 bathrooms and an open plan kitchen / living / dining area. The barn is set in 50 acres of natural woodland and fields with a lake and river. The wildlife includes herds of deer that you will see up close. The barn is situated 2 miles from the New Forest Park with its thousands of acres of national park.

Popular amenities for Winchester house rentals

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$33,682 GYDG$38,285 GYDG$36,402 GYDG$38,075 GYDG$36,820 GYDG$35,774 GYDG$37,448 GYDG$47,490 GYDG$44,979 GYDG$40,586 GYDG$38,285 GYDG$41,213 GYD
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Quick stats about house rentals in Winchester

  • Total vacation rentals

    Explore 130 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at G$4,184 GYD per night before taxes and fees

  • Verified guest reviews

    Over 6,080 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Winchester vacation rentals include wi-fi 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!

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