Holiday houses in Winchester

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Top-rated holiday rentals in Winchester

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Guest favourite

Farm stay in Headbourne Worthy

4.98 out of 5 average rating, 315 reviews

A Unique Farm Retreat

There’s something magical about The Granary. Set in acres of farmland with spectacular sunrises and sunsets, The Granary brims with rustic charm. A dreamy hideaway with an outdoor copper bath and wood fired hot tub. An idyllic get-away-from-it-all yet only 3 miles to historic Winchester. Soak amid hot water, steam and fresh air surrounded by nature and birdsong, enjoy magnificent sunsets from the ‘Sundowner’ or cosy up toasting marshmallows over the fire pit - a perfect escape to unwind.

Top Guest favourite

Guesthouse in Hampshire

4.94 out of 5 average rating, 161 reviews

Flat in Winchester

A modern 1 bedroom flat within a 20-25min walk of the historic town centre of Winchester and the Winchester train station. Buses also run regularly in to town. The flat is separate from the main house and is light and modern. It has a king bed and fully fitted kitchen. Winchester is a beautiful city with lots of historic sites to explore, including the Cathedral and Great Hall, there are also beautiful walks through the countryside and the well known Christmas Market from late November.

Top Guest favourite

Hut in Winchester

4.98 out of 5 average rating, 564 reviews

The Pigsty

The Pigsty is Winchester's first luxury woodland hideaway, with beautiful views of Vale Farm. Less than 2.5 miles from the historic centre of Winchester, this peaceful retreat is perfect for those looking to visit the city, or escape for some peace. The Pigsty’s domed design with wooden interior has a roll top bath, cosy open plan living space and decking area to enjoy dinner with sunset views. Just a few minutes walk from the famous Clarendon Way, and a 30 minute walk to the city centre.

Top Guest favourite

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

Top Guest favourite

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 favourite

Farm stay in Hampshire

4.92 out of 5 average rating, 273 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 favourite

Townhouse in Hampshire

4.99 out of 5 average rating, 193 reviews

Entire House Central Winchester 2bed private patio

In the heart of historic Winchester, Wykeham Cottage provides a perfect base for exploring the city. On beautiful St Swithun Street, overlooking the Cathedral wall, the cottage has a south-facing, private patio and an on-street parking permit for one car. Fabulous restaurants, markets, pubs, shops and riverside walks are all minutes away on foot, as are the ruins of Wolvesey Castle, Winchester College and the medieval church St Swithun-upon-Kingsgate.

Top Guest favourite

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 favourite

Guest suite in Winchester

4.89 out of 5 average rating, 166 reviews

Beautiful guest suite in rural Hampshire

Set in the grounds of a Grade II listed thatched cottage on the edge of Kings Worthy village, our annex is beautifully decorated and comfortable. With its own entrance and small private outdoor area, this property combines rural charm and handy local amenities (bus stop just outside to central Winchester and fantastic local pub just a two minute walk away). Tea and coffee are provided as well as breakfast cereals, bread/butter and fruit jams.

Guest favourite

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.

Guest favourite

Tiny home in Winchester

4.94 out of 5 average rating, 187 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

Guest favourite

Apartment in Hampshire

4.92 out of 5 average rating, 144 reviews

Newly refurbished, modern flat 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.