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Holiday Homes in Winchester, Hampshire

Self-Catering Holiday Cottages in Winchester

Escape to Winchester for a delightful self-catering break or extended stay in one of England's most captivating historical towns. Nestled in Hampshire, Winchester offers enchanting medieval streets, the majestic Winchester Cathedral, and the intriguing ruins of Wolvesey Castle. Indulge in the vibrant selection of shops, restaurants, and bars, all set against the backdrop of beautiful Winchester. Choose from a cozy apartment or a charming country cottage in the Hampshire countryside for your self-catering holiday. Whether exploring local culture or enjoying serene rural landscapes, Winchester promises a memorable getaway.

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Booking your holiday accommodation in Winchester early is recommended for the best choice of holiday rentals.

Rabbit's Warren
Fareham, Hampshire Around 15 miles from Winchester

Viewed 10 times in last week.

Sleeps 1 - 2, 1 Bedroom
Weekly price: £ 589 - £ 1526

Next Available: 18/12 to 21/12/2025

Living & Leisure Facilities: Open fire

Type of Holiday: No dogs allowed

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Fox's Den
Fareham, Hampshire Around 15 miles from Winchester

Viewed 14 times in last week.

Sleeps 2 - 4, 1 Bedroom
Weekly price: £ 604 - £ 1534

Next Available: 26/12 to 30/12/2025

Living & Leisure Facilities: Open fire

Type of Holiday: No dogs allowed

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2 Swan Green Cottages
Emery Down, Hampshire Around 18 miles from Winchester

Viewed 7 times in last week.

Sleeps 3 - 8, 3 Bedroom
Weekly price: £ 1050 - £ 1650

Sorry this property has not provided availability information.

Living & Leisure Facilities:

Type of Holiday: 2 dogs welcome

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Cottages, Apartments & Lodges in Winchester, Hampshire, England

RuralHomeStays.Com features holiday home(s) within or close to Winchester, enjoy browsing through the available options. We hope you find the perfect holiday house for you in Winchester, Hampshire.

Discover Winchester on a Self-Catering Break

Get away to Winchester on a short self-catering break or longer stay and discover not just one of Hampshire's most impressive towns, but one of England's most fascinating and appealing historical towns.

Exploring the Charm and History of Winchester

Discover charming medieval streets, the historic Winchester Cathedral, and Wolvesey Castle. Enjoy shops, restaurants, and bars in beautiful Winchester.

Cottage Stays in Winchester and the Hampshire Countryside

Whether you opt to stay in an apartment or self-catering house within Winchester or in a country cottage in the Hampshire countryside, we hope you have a wonderful self-catering holiday in Winchester.

Updated 17 November 2025