Rent Luxury Holiday Cottages in Winchester

We selected the 452 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.

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.

The Saddler's Rooms

The Saddler's Rooms

  • 6 guests

  • 3 bedrooms

Hampshire, England

There's nothing quite like escaping to the country for a few days and this converted stable barn is a million miles away from the stresses of day-to-day life. Bright, open and immaculate in every way, it's a place to relax, take a deep breath of fresh, country air and enjoy the company of your loved ones.

Sunnyside Joy

Sunnyside Joy

  • 2 guests

  • 1 bedrooms

Soberton, Southampton

Glorious greenery, fresh air and a cosy cabin – what more could you need for a rustic retreat in the English countryside? Nestled in five acres of peaceful grounds, this home welcomes you to enjoy the natural beauty of Hampshire.


We selected the top 3% holiday homes in Winchester Cottages

Explore the 452 most perfect homes in our collection

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Most popular homes in Winchester

Under the Stars

Under the Stars

  • 4 guests

  • 1 bedrooms

Amport, Andover

In The Potting Shed

In The Potting Shed

  • 2 guests

  • 1 bedrooms

East Boldre, Brockenhurst

Bay Cottage

Bay Cottage

  • 6 guests

  • 3 bedrooms

Brighstone, Newport

Dove's Rest

Dove's Rest

  • 2 guests

  • 1 bedrooms

Dinton, Salisbury

Honey Bee Cottage

Honey Bee Cottage

  • 2 guests

  • 1 bedrooms

Blandford Forum, Dorset

Dew on the Vine

Dew on the Vine

  • 6 guests

  • 3 bedrooms

Angmering, West Sussex

Penny-Farthing

Penny-Farthing

  • 4 guests

  • 2 bedrooms

Malmesbury, Wiltshire

Mane Character

Mane Character

  • 4 guests

  • 2 bedrooms

Billingshurst, West Sussex

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Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Winchester. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Winchester Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.

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