Family-friendly vacation rentals in Winchester

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Top-rated family-friendly rentals in Winchester

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

A rustic dining area features a wooden table surrounded by six chairs, with a view of exposed beams and stonework. A wood-burning stove is positioned in the corner, while a decorative vase and wine bottles add detail to the table.

Townhouse in Beaulieu

4.94 out of 5 average rating, 351 reviews

Entire Historic Cottage in Beaulieu/Parking/ Wi-Fi

Located near the Beaulieu river, this beautifully refurbished 17th Century cottage is an ideal base from which to relax and enjoy life in the New Forest. Situated on a quiet road in beautiful Beaulieu, you can walk to Monty's Inn nearby for dinner and visit the popular cafe opposite for breakfast. You may see donkeys and cows walking along the High Street! Within six miles are Lymington (ferries to the Isle of Wight), Lyndhurst, Brockenhurst and Lepe Beach. Peppa Pig World is 20 minutes' drive

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, 402 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.

Top guest favorite

A spacious living area features exposed wooden beams and warm lighting. A large bed adorned with decorative pillows is visible alongside a cozy seating arrangement. A dining table and chairs are positioned near a storage unit, while an inviting rug adds a touch of comfort.

Home in Sandleheath

4.97 out of 5 average rating, 279 reviews

Orchard Barn Spa, exclusively for you, New Forest

Orchard Barn offers a couple the perfect romantic retreat, including a new Spa Barn with hot tub and sauna, for your exclusive use during your stay. Orchard Barn is spacious, detached and oak framed, set in a large garden with pretty woodlands. It has a stunning double height ceiling, giving a truly romantic feel. The cottage is equipped to meet all your needs, from luxurious white linen by Beaumont & Brown, to robes for the spa. I aim to ensure that all my guests have a truly memorable stay.

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.

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 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!

Top guest favorite

The exterior of Colindale Cottage is depicted, showcasing a two-story structure with a light-colored façade. A garden room with glass panels is visible, along with well-kept flowerbeds and a lush green lawn. A large tree provides shade in the tranquil outdoor space.

Cottage in Hampshire

4.97 out of 5 average rating, 312 reviews

Colindale Cottage, Nether Wallop

Located between the historic cities of Winchester and Salisbury ,Colindale Cottage is an ideal base for exploring the Test Valley and beyond. Stonehenge, Highclere Castle and the New Forest are close by. The coast is approx and hour away. Dogs are welcome. Nether Wallop is a pretty village in the heart of the Test Valley close to the small town of Stockbridge with its independent shops and eateries. Nether Wallop featured in the Miss Marple series starring Joan Hickson.

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!

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.

Superhost

A spacious sleeping area features a large bed, dressed in light bedding, alongside a decorative area rug. Complementary artwork adorns the walls, with a small side table holding a lamp. Natural light filters through a high window, enhancing the cozy ambiance.

Guesthouse in Winchester

4.7 out of 5 average rating, 268 reviews

Self Contained Studio in Winchester

Just redecorated cosy and stylish self contained studio apt. with separate bathroom and kitchen, off street parking & own entrance. In the summer the private driveway can be used as courtyard patio. Parking permit avail. on request. Table and chairs and fast broadband connection and flatscreen TV. Just 2 minutes walk from train station and 7-10 from city center.