Book Luxury Holiday Rentals in Maidenhead

Award-winning homes from £98

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Home spotlights in Maidenhead

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.

Life in the Woods

Life in the Woods

  • 6 guests

  • 2 bedrooms

Harpsden, Henley-on-Thames

This charming wood-clad barn is tucked away down a tranquil private lane surrounded by idyllic Oxfordshire countryside. Inside, high vaulted ceilings and a log-burning fire bring the wow factor, and the green vistas seen through the floor-to-ceiling windows are a delight, whatever the season.

The Lark Ascending

The Lark Ascending

  • 12 guests

  • 6 bedrooms

Reading, Oxfordshire

Picture a quiet village in the Chiltern Hills, with a gorgeous redbrick house, clematis scaling its exterior and a bloom of white hydrangea to greet you upon entry. Fortunately, it’s not too good to be true, you’ll find this idyllic escape on the cusp of Sonning Common.

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.


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

Explore the 5912 most perfect homes in our collection

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Most popular homes in Maidenhead

Skindles

Skindles

  • 5 guests

  • 2 bedrooms

Maidenhead, Berkshire

Pink Slice

Pink Slice

  • 6 guests

  • 2 bedrooms

Windsor, Berkshire

Good Mews

Good Mews

  • 4 guests

  • 2 bedrooms

Henley-on-Thames, England

Stroke of Inspiration

Stroke of Inspiration

  • 4 guests

  • 2 bedrooms

Henley-on-Thames, England

Joy & Ease

Joy & Ease

  • 4 guests

  • 2 bedrooms

Warfield, Berkshire

The Belgian Ambassador

The Belgian Ambassador

  • 8 guests

  • 4 bedrooms

Bray Civil Parish, Berkshire

A Day at the Regatta

A Day at the Regatta

  • 14 guests

  • 4 bedrooms

Dorney, Buckinghamshire

The Boat Race

The Boat Race

  • 4 guests

  • 2 bedrooms

Henley-on-Thames, England

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Frequently asked questions

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