House vacation rentals in Winchester

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Top-rated house rentals in Winchester

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Top guest favorite
The exterior of a recently renovated recording studio is shown, featuring dark wooden cladding and yellow-framed windows. A welcoming front door is prominently displayed, while neatly landscaped planters add a touch of greenery. The historic church spire is visible in the background.
Home in Hampshire
4.97 out of 5 average rating, 175 reviews

Spacious and Stylish Home in Heart of Top Village

A stylish and spacious recently renovated recording studio, which has been finished to a high spec with exposed timber beams, brickwork and a stunning log burner perfect for relaxing after exploring all that Hampshire and West Sussex have to offer. There is a large double bedroom with king sized bed and ensuite bathroom, and an open plan living area with sofa beds and log burner that can accommodate up to 3 further guests. There are 3 fantastic pubs within walking distance - one only 50m away!

Guest favorite
The open living area features a vaulted wooden ceiling with pendant lighting and a modern fireplace. Comfortable seating includes two sofas and decorative cushions. Artwork is displayed along the walls, and a television is mounted above the fireplace. Light floods in through large glass doors leading to the outdoor space.
Home in Salisbury
4.92 out of 5 average rating, 145 reviews

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.

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, 342 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
The kitchen features modern cabinetry in neutral tones, with a spacious island and wooden dining table. Appliances include a stainless steel refrigerator, microwave, and coffee maker. Soft lighting enhances the ambiance, while a brick arch over the stove adds a touch of character.
Home in Hampshire
4.98 out of 5 average rating, 111 reviews

Stylish Victorian villa in Winchester

Stylish Victorian semi-detached villa in the highly sought after area of Fulflood. Off-street parking and a few minutes walk from the station with fast trains to London and the South Coast. 10 minutes walk into central Winchester with shops, eateries and the cathedral. Finished and equipped to a high standard it is the perfect base for a stay in Winchester and the surrounding countryside. Local amenities including pub, coffee shops, deli, takeaways and convenience store within 2 minutes walk.

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, 178 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, 173 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, 370 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 comfortable living area features a gray sofa adorned with cushions, complemented by a wooden dining table surrounded by four chairs. Floral curtains frame the bright windows, allowing natural light to illuminate the space, which includes a decorative fireplace along one wall.
Home in Chandler's Ford
4.99 out of 5 average rating, 194 reviews

Homely and Comfortable in a quiet location

A pretty, well-equipped and homely two bedroom terraced property situated in a quiet and lovely area of Chandler's Ford. Marwell Zoo, the New Forest, Paulton's Park/Peppa Pig World, Beaulieu, Isle of Wight ferry links and south coast beaches are a short drive away with excellent motorway and rail links. Ideal for contractor/business stays as well as families, couples and friends. Walk to the local shops and take a stroll to the beautiful Hiltingbury Lakes and local nature reserve.

Top guest favorite
A bright living area features a spacious gray sofa with red accent pillows and a large checkered ottoman. Skylights provide natural light, while framed art decorates the walls. A dining table is situated nearby, with sliding doors leading to an outdoor terrace.
Home in Pangbourne
5 out of 5 average rating, 223 reviews

A Perfect Pad in Pangbourne!

The house was 'created' in 2020 having originally been part of the village pub - its now part of a redeveloped property which also includes the owners home and a fabulous cafe called Artichoke Cafe The property is right in the heart of the picturesque riverside village of Pangbourne with its fabulous specialist shops, cafes, restaurants and pubs. Yet only ten minutes walk gets you to the countryside! The village also boasts a mainline station with direct trains to London Paddington.

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
4.95 out of 5 average rating, 699 reviews

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.

Guest favorite
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, 253 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.

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, 325 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.

Popular amenities for Winchester house rentals

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 R347 ZAR 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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