Book Luxury Short Stay Rentals in Winchester

We selected the 1180 homes worth renting in this location

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Home spotlights in Winchester

Rose of the Heart

Rose of the Heart

  • 6 guests

  • 3 bedrooms

Winfrith Newburgh, Dorset

If you’re looking to experience the magic of the English countryside, this 17th-century thatched cottage delivers the perfect solution. Nestled in the little town of Winfrith, it’s just a five-minute drive to the Jurassic Coast and some of the most beautiful spots in Dorset.

One of England's Watery Gems

One of England's Watery Gems

  • 10 guests

  • 5 bedrooms

Wraysbury, England

Nestled between two islands on the picturesque banks of the River Thames – this beautiful thatched Edwardian home built in 1903, under a fifteen-minute drive from Windsor, is the perfect riverside retreat. Watch the boats, ducks and swans on the river go by from your own private heated pool.

Beauworth's Finest

Beauworth's Finest

  • 4 guests

  • 2 bedrooms

Beauworth, Hampshire

Surrounded by the beauty of the South Downs, this converted barn is as contemporary as it is cosy. Outside, you'll have plenty of space to soak up the sunshine and admire the scenery.

Rest, Weary Traveller

Rest, Weary Traveller

  • 10 guests

  • 5 bedrooms

Itchen Valley, Hampshire

Back in the 16th century, this manor home was managed by the Clerk of the Privy Seal to Henry VIII and Elizabeth I. And this apartment within the manor extolls all the extravagance of a Tudor era country retreat.


We selected the top 3% holiday homes in Winchester Short Stay Rentals

Explore the 1180 most perfect homes in our collection

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Most popular homes in Winchester

King's Mansion

King's Mansion

  • 4 guests

  • 1 bedrooms

Windsor, Berkshire

Channelling the Sea

Channelling the Sea

  • 6 guests

  • 3 bedrooms

Selsey, West Sussex

Dew on the Vine

Dew on the Vine

  • 6 guests

  • 3 bedrooms

Angmering, West Sussex

Queen of Queens

Queen of Queens

  • 10 guests

  • 5 bedrooms

Bognor Regis, West Sussex

Days by the River

Days by the River

  • 8 guests

  • 4 bedrooms

Corhampton and Meonstoke, Hampshire

Country Courtyard

Country Courtyard

  • 8 guests

  • 4 bedrooms

Itchen Valley, Hampshire

Stud Cottage

Stud Cottage

  • 2 guests

  • 1 bedrooms

Billingshurst, West Sussex

Watford Magic

Watford Magic

  • 9 guests

  • 5 bedrooms

Watford District, Hertfordshire

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Frequently asked questions

Browse our curated collection of Short Stay Rentals in Winchester. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Winchester luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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