Book Luxury Holiday Rentals in Old Windsor

Award-winning homes from £98

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Home spotlights in Old Windsor

A Day at the Regatta

A Day at the Regatta

  • 14 guests

  • 4 bedrooms

Dorney, Buckinghamshire

Part of the historic Estate of Dorney Court, this timber-framed house dates back to the sixteenth century and is a magical blend of heritage and modernity. The former great hall is emblematic of this.

Read My Mind

Read My Mind

  • 2 guests

  • 1 bedrooms

Reading, Berkshire

Enviably situated in the heart of Reading, this place is perfect for those who are always on the go. If you need to head out of town, the train station is less than a ten-minute walk away, connecting you to London Paddington in around forty minutes.

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.

The Queen's Lodge

The Queen's Lodge

  • 4 guests

  • 2 bedrooms

Windsor, Berkshire

If you’ve ever wondered what it would be like to live next door to a member of the royal family, this place might have the answers. Situated just a few metres from iconic Windsor Castle, this simple but stylish apartment is a great base for those looking to get up close and personal with British royalty, tucked just round the corner from the late Queen’s historic weekend home.


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

Explore the 5492 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

Ebony & Ivory

Ebony & Ivory

  • 7 guests

  • 4 bedrooms

Highway, Maidenhead

Eton Oasis

Eton Oasis

  • 6 guests

  • 2 bedrooms

Eton, Windsor

Teak On White

Teak On White

  • 8 guests

  • 4 bedrooms

Reading, Berkshire

Painted White

Painted White

  • 5 guests

  • 3 bedrooms

Esher, Surrey

Escapade

Escapade

  • 10 guests

  • 5 bedrooms

Eton, Windsor

Britannia Jewel

Britannia Jewel

  • 5 guests

  • 3 bedrooms

Windsor, Berkshire

Fond Memories

Fond Memories

  • 10 guests

  • 5 bedrooms

Windsor, Berkshire

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Frequently asked questions

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