Book Luxury Holiday Rentals in Old Windsor

Award-winning homes from £98!

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Home spotlights in Old Windsor

Nom de Plume

Nom de Plume

  • 9 guests

  • 5 bedrooms

Dorney, Buckinghamshire

One of the many barn conversions peppered across the British countryside, this home is a fine example of the great sense of space and light that's typical of the very best of these former agricultural buildings. Behind the front door, you'll find no clue as to the property's prior life – only stark white walls, shiny wooden floors and a super-sleek kitchen complete with a huge island that would happily slot into the most contemporary of city apartments.

Green on My Mind

Green on My Mind

  • 10 guests

  • 5 bedrooms

Shere, Guildford

Just a five-minute walk from the picture-perfect village of Shere in the Surrey Hills, this place is a much-loved family home. Set in five acres of private grounds, with views across the rolling hills, it's bound to be a hit with lovers of the great outdoors, with excellent hiking and cycling routes from your door.

The Great British Retreat

The Great British Retreat

  • 18 guests

  • 9 bedrooms

Bray Civil Parish, Berkshire

Set within 40 acres of gardens, paddocks and woodland just west of Windsor, this home is a true escape from it all. Blending contemporary interiors into a traditional English setting, there’s so much to love here.

Royal Next Door

Royal Next Door

  • 6 guests

  • 3 bedrooms

Windsor, Berkshire

Right in the heart of Windsor, this central home puts you within minutes of the town's stylish boutiques, award-winning restaurants and traditional pubs. At the same time, the home is surrounded by parkland and greenspace, so it feels more rural than it actually is.


We selected the top 3% holiday homes in Old Windsor Holiday Rentals

Explore the 5540 most perfect homes in our collection

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Most popular homes in Old Windsor

The Windsor Crown

The Windsor Crown

  • 5 guests

  • 3 bedrooms

Old Windsor, England

Fond Memories

Fond Memories

  • 10 guests

  • 5 bedrooms

Windsor, Berkshire

The Guildford Gully

The Guildford Gully

  • 12 guests

  • 6 bedrooms

Windsor, Berkshire

Good Mews

Good Mews

  • 4 guests

  • 2 bedrooms

Henley-on-Thames, England

Painted White

Painted White

  • 5 guests

  • 3 bedrooms

Esher, Surrey

Escapade

Escapade

  • 10 guests

  • 5 bedrooms

Eton, Windsor

The Queen's Lodge

The Queen's Lodge

  • 4 guests

  • 2 bedrooms

Windsor, Berkshire

Secret Garden Games

Secret Garden Games

  • 8 guests

  • 5 bedrooms

Burnham, Slough

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Old Windsor. 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 Old Windsor 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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