Winchester Weekend House Rentals

We selected the 1038 homes worth renting in this location

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Home spotlights in Winchester

Cinnamon & Ginger

Cinnamon & Ginger

  • 2 guests

  • 1 bedrooms

Winchester, Hampshire

Nestled in the rolling hills of Hampshire, this charming flintstone cottage has sprawling views of the surrounding countryside and easy access to walking trails that take you through fields and woods and into picturesque villages with charming pubs. Roaming around this area (including visiting nearby Winchester) feels a bit like taking a step back in history – the air is fresher, the pace of life slower, and the atmosphere much more relaxed.

English Splendour

English Splendour

  • 14 guests

  • 7 bedrooms

Itchen Valley, Hampshire

Beautiful inside and out. This villa's contemporary 1950's Italian-inspired interior gives way to sprawling Hampshire farmland.

Autumn's Being

Autumn's Being

  • 8 guests

  • 3 bedrooms

Itchen Valley, Hampshire

You'll find this 18th-century cottage in the heart of the South Downs, nestled on the edge of the illustrious Avington Park. Cosiness personified, the snug sitting room has a crackling wood-burner and squishy sofas that beckon for lounging, either with a glass of wine on chilly evenings or a good book on winter afternoons.

Royal Rumble

Royal Rumble

  • 50 guests

  • 25 bedrooms

Itchen Valley, Hampshire

This remarkable country mansion has had quite the tumultuous history. The estate dates back to 961 and is listed in the Domesday Book.


We selected the top 3% holiday homes in Winchester Weekend House Rentals

Explore the 1038 most perfect homes in our collection

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Most popular homes in Winchester

Country Courtyard

Country Courtyard

  • 8 guests

  • 4 bedrooms

Itchen Valley, Hampshire

English Renaissance

English Renaissance

  • 6 guests

  • 3 bedrooms

Itchen Valley, Hampshire

Rest, Weary Traveller

Rest, Weary Traveller

  • 10 guests

  • 5 bedrooms

Itchen Valley, Hampshire

The Saddler's Rooms

The Saddler's Rooms

  • 6 guests

  • 3 bedrooms

Hampshire, England

Cities & Villages

Cities & Villages

  • 4 guests

  • 2 bedrooms

Southampton City Centre, Southampton

Southampton Star

Southampton Star

  • 2 guests

  • 1 bedrooms

Southampton City Centre, Southampton

Days by the River

Days by the River

  • 8 guests

  • 4 bedrooms

Corhampton and Meonstoke, Hampshire

Hamble Haven

Hamble Haven

  • 8 guests

  • 4 bedrooms

Bursledon, Southampton

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Check upcoming rates & availability for Winchester Weekend House Rentals


Frequently asked questions

Looking to book a holiday rental for the weekend in Winchester? You've come to the right place: we’re the official selection of the world’s best homes. Our collection of weekend rentals in Winchester come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. We obsessively check each home for you, so you can book with peace of mind. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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