Family-friendly holiday rentals in Winchester

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.

Family · Kitchen · Comfort

Nettlebed Farm Holiday Lets, Barn1 of 3

* From £124 p/n +Airbnb charges Beautiful oak barn set in traditional english countryside. Placed with own access within 15 acres of private woodland and grazing land, away from the main road for peace and tranquility. Guests are able to have privacy for relaxation and enjoy views of horses grazing and the comings and goings of the British wildlife. Just 4 minute drive to the market town of Bishops Waltham or you can join and follow the infamous Pilgrims Trail and walk there in just 30 minutes.

Family · Kitchen · Access

The Nest

This charming 3-bed cottage with private parking and garden is situated in Shawford, near to the historic town of Winchester. Walks along the River Itchen, swimming, fishing and picnic spots are on your doorstep. Local pub in Shawford and pubs in nearby village of Twyford. Winchester is also accessible by foot ( 45 mins) or a short 5 minute train or bus away. London is an hour by train and other local attractions include Marwell Zoo, Peppa Pig World, South Coast, Portsmouth and New Forest.

Kitchen · Family · Walkability

The Loft with free off road parking

A self-contained studio by apartment with kitchen facilities, double bed, sofa and TV. En-suite toilet and shower room. Free off street parking on the doorstep. Situated 5-10 minutes walk from Winchester's historic city centre and even closer to the widely renowned Black Boy pub. Within 150 metres of the South Downs Way. Just a few minutes walk from the Everyone Active Winchester Sports Centre. The apartment is accessed via an external staircase and so may not suit those with mobility issues.

Family · Kitchen · View

Stable Cottage Beauworth Southdowns Hampshire

Nestled within the South Downs National Park, this charming countryside escape offers uninterrupted views across open fields where sheep graze. Wake up to breathtaking bedroom views, explore the surrounding countryside and historic Winchester, and in the winter, cosy up beside the crackling log burner. Thoughtfully equipped for families with babies and children, as well as couples seeking a peaceful getaway, it’s the perfect retreat to unwind and enjoy Hampshire’s beautiful landscape.

Family · Indoor spaces · Bathroom

Central Winchester 1 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.

Indoor spaces · Family · Check-in

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.

Indoor spaces · Kitchen · Quiet

The Woodshed

The Woodshed is right in the heart of the South Downs National Park, between the villages of Warnford and Exton, a secluded and peaceful space surrounded by a working farm. The Woodshed has a view of Old Winchester Hill that is magic. Activities in the area include biking, hiking, and angling, and three of the best pubs in Hampshire are within a 5 mile radius. As we are a little distance from the main track, I am happy to come and collect guests from Exton if walking.

Indoor spaces · Kitchen · Beach

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.

Family · Kitchen · Comfort

Stylish Apartment • Central Winchester

Situated in the heart of Winchester, this newly refurbished two-bedroom apartment with its own private entrance offers a stylish and comfortable stay for couples, friends and families. Modern décor and thoughtful design create a cosy space to relax after exploring the city’s historic streets, shops and cathedral. You’re just steps from the popular St James Tavern, a welcoming traditional pub serving excellent locally sourced food.

Kitchen · Indoor spaces · Wifi

The Cottage in Compton

Come and enjoy a stay in The Cottage, located in the grounds of our 17th Century converted Barn. Enjoy a unique location on the edge of Winchester with direct access to the countryside. The Cottage has been recently extended and refurbished with everything you will need to make your stay enjoyable. A perfect place for a break to explore all the wonderful things that Winchester has to offer!

Kitchen · Indoor spaces · Layout

Stunning oak-framed "Loft House"

The "Loft House" was built in 2017 and has been freshly decorated to create a calm and stylish space. It is situated in a truly beautiful and tranquil rural location, and is a fantastic base to explore this lovely part of Hampshire. It is a cosy compact space so ideal for a couple or two adults, and could also accommodate up to two children. It is not suitable for more than two adults.

Indoor spaces · Kitchen · Accuracy