Book Luxury Holiday Rentals in Winchester

Award-winning homes from £98

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Home spotlights in Winchester

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.

Under the Stars

Under the Stars

  • 4 guests

  • 1 bedrooms

Amport, Andover

Glamping never looked so good than at this charming cabin nestled within a wild-flower meadow of a 2500-acre family-owned farm estate. Don't be fooled by its unassuming aluminum exterior.

A Little Peach

A Little Peach

  • 2 guests

  • 1 bedrooms

Wimborne Saint Giles, Wimborne

A historic gatehouse on the grounds of the Shaftesbury Estate in rural Dorset, this petite one-bed lodge has recently undergone a loving refurb by one of the estate owners, Lady Shaftesbury. She obviously has a great eye for design, as her palette of delicious apricot and duck egg blue stylishly updates this vintage cottage into not just a twenty-first-century home, but a home with charm and character.

Country Courtyard

Country Courtyard

  • 8 guests

  • 4 bedrooms

Itchen Valley, Hampshire

Set within 150 acres of private parkland majestically situated along the banks of the River Itchen, make the most of an exceptional opportunity to experience life in a privately owned stately home that includes both Charles II and George IV among its illustrious guests. With wonderful rooms overlooking the charming Italian garden, this beautiful ground-floor flat has four luxurious bedrooms that offer up to eight guests a chance to enjoy the good life.


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

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Most popular homes in Winchester

Royal Rumble

Royal Rumble

  • 50 guests

  • 25 bedrooms

Itchen Valley, Hampshire

Mane Character

Mane Character

  • 4 guests

  • 2 bedrooms

Billingshurst, West Sussex

Hammoon Manor

Hammoon Manor

  • 8 guests

  • 4 bedrooms

Hammoon, Sturminster Newton

Dove's Rest

Dove's Rest

  • 2 guests

  • 1 bedrooms

Dinton, Salisbury

Channelling the Sea

Channelling the Sea

  • 6 guests

  • 3 bedrooms

Selsey, West Sussex

Rest, Weary Traveller

Rest, Weary Traveller

  • 10 guests

  • 5 bedrooms

Itchen Valley, Hampshire

Autumn's Being

Autumn's Being

  • 8 guests

  • 3 bedrooms

Itchen Valley, Hampshire

The Swan's Feather

The Swan's Feather

  • 2 guests

  • 1 bedrooms

Swanage, Dorset

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Winchester. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Winchester has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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