Winchester Luxury Rentals

We selected the 124 homes worth renting in this location

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Home spotlights in Winchester

Millstone

Millstone

  • 4 guests

  • 2 bedrooms

Bosham, West Sussex

A gorgeous period cottage on the banks of the millstream, this home puts you in the heart of the picturesque English coastal village of Bosham. It’s incredibly quiet here, with barely any sound other than the burbling of the stream and the quacking of ducks.

Rolling Rest

Rolling Rest

  • 2 guests

  • 1 bedrooms

Combe, Berkshire

Whisk your loved one away to this rural retreat on the outskirts of Hungerford, Berkshire. The countryside surroundings are idyllic, especially from the heated pool – it’s exclusively yours to use between June and September.

The Blue Bells

The Blue Bells

  • 20 guests

  • 7 bedrooms

Hawkesbury, South Gloucestershire

Originally built for the Prime Minister in the 1800s, this home has been known to hold some pretty impressive parties over the years. Today it exists as a private retreat for friends and families to celebrate their own special event, or simply escape from it all in the heart of the Cotswolds.

Boysenberries

Boysenberries

  • 18 guests

  • 9 bedrooms

Lockinge, Wantage

This exquisite home offers a tailor-made experience for those wanting luxury, pro-level hosting, with the possibility of a fully catered stay accompanied by some seriously high-end food. It's the perfect place for extended families or a group of couples to get together to hold a special celebration or event together.


We selected the top 3% holiday homes in Winchester Luxury Rentals

Explore the 124 most perfect homes in our collection

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Most popular homes in Winchester

Brail Barn

Brail Barn

  • 4 guests

  • 2 bedrooms

Marlborough, Wiltshire

A Home with Charm

A Home with Charm

  • 18 guests

  • 9 bedrooms

Kingscote, Tetbury

A Deeper Peace

A Deeper Peace

  • 4 guests

  • 2 bedrooms

Funtington, Chichester

One of England's Watery Gems

One of England's Watery Gems

  • 10 guests

  • 5 bedrooms

Wraysbury, England

The Tudor Dream

The Tudor Dream

  • 4 guests

  • 2 bedrooms

Tetbury, England

The Light of Nature

The Light of Nature

  • 14 guests

  • 8 bedrooms

Tormarton, South Gloucestershire

A Wild Flower

A Wild Flower

  • 8 guests

  • 4 bedrooms

Cirencester, Gloucestershire

The Colour of Glass

The Colour of Glass

  • 16 guests

  • 6 bedrooms

Shanklin, Isle of Wight

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A handpicked selection of the best luxury homes in Winchester, as chosen by the experts who've visited and vetted thousands of the city's homes. Luxurious interiors, sumptuous bedrooms and prime city centre locations. Available for short and extended stays.

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