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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Top guest favorite

A light-filled living area features a comfortable gray sofa adorned with patterned cushions. A small, cozy armchair sits nearby, and a wooden coffee table is positioned in front. Natural light streams through the window, highlighting a light blue wall and decorative shelf.

Condo

4.97 out of 5 average rating, 129 reviews

Spacious central 2 bedroom apartment+ free parking

A spacious family-friendly 2 double/twin bedroom first floor flat located in the lovely Hyde area of central Winchester. Provides easy access to the city centre with all that the city offers. Only 5 minutes stroll to the train station. This apartment is close to all the historical sites and wide variety of restaurants and cafes which you'll enjoy as well as the cathedral and its impressive grounds. Winchester Christmas market and the city's magical atmosphere should be on everybody's calendar.

Top guest favorite

An aerial view captures the serene landscape surrounding the property, featuring a winding driveway leading through open fields. Lush trees and greenery frame the scene, with a clear blue sky dotted with clouds above, providing a sense of tranquility and natural beauty.

Barn

4.95 out of 5 average rating, 487 reviews

Cow Shed - Barn

A spacious ground floor suite. Watch fiery sun sets & brown eyed cows walking past to drink. Enjoy outdoor & indoor dining. A super king bed allows for space and a good nights rest with a luxurious en-suite shower to invigorate. Peaceful location but not far from local town. 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 Cow Shed is full then look up the Hay Loft. Our first floor suite.

Top guest favorite

Two distinct entrances are visible, each framed by elegant archways. A decorative black iron railing separates the front door area from the sidewalk, while light green planters with small shrubs add a touch of greenery to the scene. Large windows allow natural light to fill the interior.

Guest suite

4.97 out of 5 average rating, 387 reviews

Own Front Door

Welcome to the beautiful city of Winchester! I have self contained central accommodation comprising of a double bedroom with en-suite shower room, a lounge with fridge/tea/coffee making facilities and your own private front door accessed from the street at ground level. The accommodation has been part of a massive renovation of the main house, now fully completed. Dating from the 1850’s it still retains a Victorian feel with high ceilings and sash windows. It is a lovely light, airy space.

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

4.95 out of 5 average rating, 695 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 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

4.83 out of 5 average rating, 474 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

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

4.97 out of 5 average rating, 537 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

A cozy studio bedroom features a spacious bed with white linens and a decorative pillow. Bedside tables with lamps flank each side of the bed. Light wood flooring complements the natural light from the window, while a green plant adds a touch of nature to the space.

Farm stay

4.91 out of 5 average rating, 317 reviews

Room with a view

You’ll love sharing photos of this unique place with your friends. Room with a View is a cosy and bright studio room located in the outskirts of the rural village of Owslebury. Just a 5-mile drive from the medieval city of Winchester, Room with a View is situated in a prime location, perfect for a serene getaway or business stay. Secluded from the busy bustle of the city, yet a swift 10-minute drive, Room with a View is surrounded by acres of fields and beautiful views.

Top guest favorite

The lounge area features a comfortable sofa adorned with colorful cushions and a light rug underfoot. A small armchair adds seating options, while natural light filters through the large windows, illuminating the room. A round coffee table rests in the center, enhancing the cozy atmosphere.

Apartment

4.95 out of 5 average rating, 351 reviews

Central Winchester garden flat, permit parking

Winchester City Centre- Bijou, charming, characterful, homely, warm and cosy self contained one bedroom flat with free permit parking and luxuriously large bath tub with shower, private garden with patio for alfresco dining. Fully equipped galley kitchen for self - catering. Only a five minute level walk to the central High Street and Cathedral, with the world famous Christmas Market through November and December. Less than ten minutes walk from the Railway Station.

Top guest favorite

A modern studio layout is displayed, featuring a kitchenette with a microwave, oven, and fridge. Bright yellow accents enhance the design. A small dining area with two barstools is positioned near a flat-screen TV. Natural light fills the space through a window with a light-filtering blind.

Guest suite

4.97 out of 5 average rating, 178 reviews

Pretty self contained annexe

Pretty, self contained annexe with its own entrance, located between the historic city of Winchester & Southampton and on the doorstep of the New Forest National Park. Great travel links - M3/M27, Southampton Airport & Southampton Parkway station. Studio comprises double bed, kitchen with oven, hob, fridge & microwave. Breakfast bar, which doubles as a workspace, shower room and shared use of patio and garden. We also have a young, bouncy dog!

Top guest favorite

A spacious living area features a comfortable sectional sofa with colorful cushions, positioned near large glass doors that open to a vibrant outdoor space. Natural light illuminates the room, highlighting the modern furniture and stylish decor.

Tiny home

4.95 out of 5 average rating, 210 reviews

The Hidden house in Winchester

The Hidden House is a slice of modern luxury tucked away in the heart of Winchester. Detached and private, this space is perfectly placed for exploring Winchester and all it has to offer. Our guests also love hiding away and making use of the big TV setup and Hotel Chocolat Velvetiser! Don't take our word for it - check out our reviews. Winchester High Street/The Cathedral - 10 min walk Winchester Train Station - 5 min walk

Top guest favorite

The living room features a light and airy design, showcasing a two-seater sofa and a separate sofa bed. A dining table for four is centered in the space, complemented by a fireplace and a wall-mounted TV. Decorative plants enhance the welcoming atmosphere.

Apartment

4.93 out of 5 average rating, 174 reviews

Modern Apartment Central Winchester

Situated in the heart of Winchester, this newly refurbished 2-bedroom apartment with its own private entrance and modern décor provides a well thought out space for friends, couples & families. This cosy home provides an excellent upmarket base to explore Winchester. A stone’s throw to the city’s favourite pub, St James Tavern, a warm welcoming traditional pub which serves excellent locally sourced home cooked food.

Top 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

4.94 out of 5 average rating, 776 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.