House vacation rentals in City of Winchester

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Top-rated house rentals in City of Winchester

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Guest favorite

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

4.85 out of 5 average rating, 385 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.

Superhost

A private deck featuring a spacious hot tub surrounded by lush greenery and a wooden railing. Outdoor furniture, including a round glass table with six woven chairs, is positioned nearby, creating a comfortable space for relaxation and enjoyment.

Home in Pitt

4.89 out of 5 average rating, 161 reviews

Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB

Award winning, 5 star 3 bedroom, 2 bathroom log cabin with private HOT TUB (sleeps 6). Located in the centre of a 18 hole Championship Golf Course just 3 miles from the historic city centre of Winchester. Vaulted ceilings and exposed wood provides a tranquil setting. Fully equipped kitchen, open plan living-dinning area with cosy fire, smart TV with streaming services. Living room opens onto a private deck with HOT TUB and views over the guest putting green, ancient woodland and nature trails.

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, 102 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, 165 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, 148 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!

Top 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, 359 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

Superhost

A private hot tub rests on a stone patio surrounded by lush greenery. Two blue chairs are positioned nearby, inviting relaxation. A wooden railing defines the area, and the building features a sloped roof with skylights, allowing natural light to enhance the space.

Home in Owslebury

4.79 out of 5 average rating, 201 reviews

Boxwood, Owslebury, Winchester

Boxwood is on the edge of Owslebury, a picturesque village just south of Winchester. It has a large open planning living space with Bi Fold doors that open onto the hot tub terrace. It has 1 bedroom on ground floor level and a cloak/shower room. Upstairs there are 3 bedrooms 1 twin, 1 double and 1 king with ensuite and a large bathroom with bath and separate shower. There are 2 terraces one with private hot tub and parking at the end of a shared drive. Steps down to the door for access.

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, 177 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

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, 666 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.

Top guest favorite

A bright and welcoming living area features a striped sofa and a small dining table set for two. A colorful area rug lies beneath a wooden coffee table. Natural light filters through sheer curtains, enhancing the cozy atmosphere of the space.

Home in Hampshire

4.99 out of 5 average rating, 115 reviews

One bedroom house in Waterlooville. An ideal base.

This is my small one bed house which is ideal for exploring SE Hampshire & W Sussex. The new king size bed, lounge, kitchen & bathroom provide an ideal base, located in a quiet suburban location. There is excellent access to the A3M & A27, so Portsmouth, Petersfield, Chichester and the South Downs lie within easy reach. I have a nice garden and car bay for my visitors and include broadband and gas central heating which I hope will make your visit relaxing, convenient and enjoyable.

Top 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, 311 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.

Guest favorite

A balcony features two white, ornate chairs paired with a small round table. Potted plants of various sizes embellish the area. A lush green tree and neighboring buildings are visible in the background, set against a clear blue sky.

Home in Hampshire

4.88 out of 5 average rating, 297 reviews

City Centre Riverside Gem With Parking.

An amazing two bedroom period cottage that is superbly located for all of Winchester's amenities, adjacent to the city mill and just a few steps away from the High Street. The cottage offers city living in a delightful tucked away location backing onto the River Itchen and only seconds from all the city centre has to offer. The house suits all needs, a romantic weekend, a South Downs Way stop over, family break and equally a business trip.