Book Luxury Holiday Rentals in Old Windsor

Award-winning homes from £98

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Home spotlights in Old Windsor

Escapade

Escapade

  • 10 guests

  • 5 bedrooms

Eton, Windsor

If Windsor Castle is on your sightseeing list, then you've come to the right place. You'll be staying less than a ten-minute walk away, and near to the train station that can take you up to London in forty minutes.

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.

Teak On White

Teak On White

  • 8 guests

  • 4 bedrooms

Reading, Berkshire

Spread out across three floors in this modern townhouse. Unique wooden furniture imported from India adds a touch of elegance to the minimalist, white decor.

Britannia Jewel

Britannia Jewel

  • 5 guests

  • 3 bedrooms

Windsor, Berkshire

Sitting on a quiet residential street in central Windsor, this beautiful upper maisonette offers a warm and welcoming base for those looking to experience the town’s rich and royal history, as well as the delights of nearby Eton, Ascot and Legoland. Laid out over three floors, you’ll find plenty of space to socialise as well as opportunities to steal yourself await for some relaxing privacy.


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

Explore the 5864 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

Boudica In Blue

Boudica In Blue

  • 4 guests

  • 1 bedrooms

St Albans, Hertfordshire

The Great British Retreat

The Great British Retreat

  • 18 guests

  • 9 bedrooms

Bray Civil Parish, Berkshire

Wraysbury Dream

Wraysbury Dream

  • 10 guests

  • 4 bedrooms

Wraysbury, England

The Queen's Lodge

The Queen's Lodge

  • 4 guests

  • 2 bedrooms

Windsor, Berkshire

Grace & Light

Grace & Light

  • 4 guests

  • 2 bedrooms

East Molesey, England

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Check upcoming rates & availability for Old Windsor Holiday Rentals


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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