Family-friendly vacation rentals in City of Winchester

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Top-rated family-friendly rentals in City of Winchester

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Guest favorite

The bungalow's exterior features a combination of brick and wood with a textured gabled roof. Flower pots and beds with colorful blooms line the pathway, leading to large windows that allow natural light into the interior.

Bungalow in Eastleigh

4.94 out of 5 average rating, 401 reviews

One bedroom home.

Relax and make yourself at home in this comfortable bungalow with sunny lounge, fully equiped kitchen/diner and bathroom. Situated in a quiet cul-de-sac in the village of Bishopstoke on the outskirts of Eastleigh. The M27 and M3 motorways and Southampton Airport are just a few miles away. The historic City of Winchester is an easy drive. Whether you are on your way to explore the South West, visiting family or friends or just wanting a short break, we offer a convenient home away from home.

Guest favorite

A private outdoor area is presented with two green metal chairs and a small round table. Planters with flowers enhance the scene, and large glass doors lead into the interior space, allowing natural light to fill the area.

Guesthouse in Winchester

4.94 out of 5 average rating, 287 reviews

Water Meadows Lodge beside Winchester South Downs

"Riverside" Garden Lodge is separate, secure and sunny with a private garden and free parking in St Cross village Winchester, beside the Water Meadows and South Downs. Only 15 minutes walk from the centre via the famous Water Meadow paths or road's celebrated inns you have an ideal location to enjoy this historic city. Finished to high standards, the double bedroom, spacious living / dining room, kitchen, shower / loo have the essential luxuries. Plus Fast WiFi, 42" Smart TV and Laundry service.

Guest favorite

The exterior of the spacious annex is set amidst a well-maintained garden, featuring lush green grass, varied shrubbery, and decorative landscaping. A patio area can be seen, complemented by outdoor seating options and natural sunlight filtering through the surrounding trees.

Guest suite in Liphook

4.9 out of 5 average rating, 385 reviews

Large guest house

The spacious annex has a separate guest entrance and off-street parking. Guests can use the private patio and there are facilities for breakfast of toast & cereal (included). Located down a private drive in the heart of Liphook within walking distance of many local amenities (3 pubs, supermarket, cinema, take aways). The train station is only a 7 minute walk away and a 2 minute walk from a bus stop. We are on the edge of the South Downs National Park with some stunning walks from the house.

Guest favorite

The exterior of the apartment features a modern wooden structure with large glass windows, offering a view of the semi-rural surroundings. A set of steps leads to the entrance, and a well-maintained lawn is visible in the foreground with trees lining the background.

Apartment in Winchester

4.91 out of 5 average rating, 356 reviews

Copper Beech, a secluded two bed apartment

Copper Beech is spacious & modern apartment in a semi-rural location close to Winchester. This apartment has two large king size bedrooms; both with ensuite bathrooms, large lounge/dining area and a well equipped kitchen. One of the bedrooms can sleep up to 4 guests with a daybed (with two full single size beds) plus kingsize bed. Parking is available for two standard-sized vehicles - one blocking in the other. There is a trampoline in a large shared garden for children to play on.

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

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

The exterior of the barn-like structure features a sloping roof with wooden shingles and a glass-front entrance. The door is framed by sturdy wooden pillars. A grassy area is visible in the foreground, providing a natural setting with a backdrop of fields and trees.

Barn in Hampshire

4.97 out of 5 average rating, 351 reviews

Hay Loft - Barn

A spacious first floor suite with uninterrupted views across the fields. Enjoy indoor or outdoor dining. A super king bed aids restful sleep with a rain shower en-suite. It benefits from having a small self contained bunk room for the children giving space but having them with you. A very small but well equipped kitchen with essentials provided. If you need us we are on site but otherwise will leave you in peace to enjoy your stay. If the Hay Loft is full - look up the Cow Shed.

Top guest favorite

A charming brick and flint building is surrounded by neatly trimmed bushes and a well-maintained garden. Two wooden chairs and a small table are set outside, inviting guests to enjoy the tranquil rural setting under clear skies.

Guesthouse in Winchester

4.97 out of 5 average rating, 518 reviews

Idyllic Hideaway Ham Green Cottage near Winchester

The Orchard Studio at Ham Green Cottage is a pretty brick and flint building tucked away in a corner of our truly English country garden. You are completely private. We are family-friendly and you can expect a comfortable stay and warm welcome. We are in a village close to the historic city of Winchester, however our setting is completely rural and quiet. We have a fantastic village pub or there are lots of places to chose from in Winchester itself - the best of both worlds!

Guest favorite

A pathway leads to a secluded studio nestled within a leafy garden. The entrance features wooden decking and large glass doors that provide a view into the cozy interior. Surrounding greenery adds to the privacy of the space.

Tiny home in Winchester

4.83 out of 5 average rating, 458 reviews

Cosy rural hideaway, Hursley, near Winchester

Fantastic rural retreat! Gorgeous cosy space, very private with own secluded garden. Everything that you need for a relaxing break. Five miles from both Winchester and Romsey, a fifteen minute walk to the lovely village of Hursley with its two pubs and great walks! Perfect for IBM Hursley, Peppa Pig World/Paultons Park, the New Forest (25 minutes) and beaches (40 minutes). You can be in Southampton with cinemas, bowling, shopping etc in 20 minutes. A great exploring base!

Guest favorite

A mature garden area is visible, featuring a combination of flat grass and colorful flower borders. The garden is complemented by a large shrub and the annexe is seen with a wooden door, reflecting a natural, serene environment.

Apartment in Southampton

4.88 out of 5 average rating, 319 reviews

Luxury Garden annexe in a great location

A self-contained annexe recently refurbished with separate entrance situated in a mature garden located beside the busy A33 road into Southampton with secure gated parking for one car. The annexe consists of a 3.4 X 4.0m living room/kitchen with a 2.8 X 3.2m rear bedroom with ensuite bathroom. It is well located for the airport and railway station, with bus stops to the city centre or Winchester on the road just outside. An electric charging point is available.

Top guest favorite

The exterior of the barn reveals a charming brick facade, topped with a slate roof. Colorful flowers, including orange and purple blooms, are arranged around a paved patio area, contributing to a serene garden environment. Large windows allow natural light to fill the space.

Barn in New Alresford

4.97 out of 5 average rating, 105 reviews

Self contained annex . In the heart of Alresford

Delightful , self contained annexed barn with its own entrance . Sympathetically converted 18th century brick and flint barn with original features situated in the pretty market town of Alresford,Hampshire. Very near to the river Arle with picturesque walks, ducks, swans and all within 5 minutes walk to the centre of town. Ideally situated for The Grange Festival opera Northington and the ancient city of Winchester.

Guest favorite

A bright studio space features light wooden flooring and calming blue accents. A king-size bed with a geometric patterned blanket is complemented by a turquoise sofa bed. Large glass doors open to the outdoor space, framed by floor-length curtains that enhance natural light.

Loft in Chandler's Ford

4.93 out of 5 average rating, 738 reviews

Stylish Studio Annexe in Chandlers Ford Location

Welcome to my bright and inviting studio annexe, perfectly positioned for both business and leisure stays in Hampshire. Featuring a romantic Juliet balcony that bathes the space in warm afternoon sun, this self-contained retreat offers modern comfort with convenient access to the region's most popular destinations. The private entrance and dedicated parking ensure a seamless stay from arrival to departure.