Book Luxury Winter Rentals in Maidenhead

We selected the 5912 homes worth renting in this location

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Home spotlights in Maidenhead

Ebony & Ivory

Ebony & Ivory

  • 7 guests

  • 4 bedrooms

Highway, Maidenhead

This home located just outside of Maidenhead is certainly one of the more pared-back properties in our collection, but it's so well-executed that we felt compelled to include it. The ivory walls, shiny wooden floors and large windows combine together to make the interior feel bright and inviting.

Skindles

Skindles

  • 5 guests

  • 2 bedrooms

Maidenhead, Berkshire

Bathed in natural light, decked out with comfortable furniture and blessed with a spacious open-plan layout, this flat in the centre of Maidenhead is perfect for anyone looking to explore the best of Berkshire. A favourite among the Edwardian upper classes who didn't have the time or inclination to travel as far as Bath, Maidenhead is on the up and up.

Secret Garden Games

Secret Garden Games

  • 8 guests

  • 5 bedrooms

Burnham, Slough

Despite being tucked away on the outskirts of Burnham village, it’s worth noting that this historic home is situated by the side of an – albeit fairly quiet – road. Although both cosy and capacious – featuring five bedrooms as well as separate breakfast, dining and sitting rooms – we’ll bet it’s this home’s four-poster bedroom and en-suite marble bathroom you’ll be fighting over.

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.


We selected the top 3% holiday homes in Maidenhead Vacation Rentals for Winter

Explore the 5912 most perfect homes in our collection

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Most popular homes in Maidenhead

Nom de Plume

Nom de Plume

  • 9 guests

  • 5 bedrooms

Dorney, Buckinghamshire

The Queen's Lodge

The Queen's Lodge

  • 4 guests

  • 2 bedrooms

Windsor, Berkshire

The Belgian Ambassador

The Belgian Ambassador

  • 8 guests

  • 4 bedrooms

Bray Civil Parish, Berkshire

River Rest

River Rest

  • 2 guests

  • 1 bedrooms

Marlow, England

Britannia Jewel

Britannia Jewel

  • 5 guests

  • 3 bedrooms

Windsor, Berkshire

Sunsets & Swan Feathers

Sunsets & Swan Feathers

  • 7 guests

  • 4 bedrooms

Eton, Windsor

One of England's Watery Gems

One of England's Watery Gems

  • 10 guests

  • 5 bedrooms

Wraysbury, England

Gather & See

Gather & See

  • 10 guests

  • 5 bedrooms

Windsor, Berkshire

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Check upcoming rates & availability for Maidenhead Vacation Rentals for Winter


Frequently asked questions

Browse our remarkable collection of luxury Vacation Rentals for Winter in Maidenhead. As only the top 3% of homes go on to become Plum Award winners, you can be certain that your chosen home will be ideal for you. Each home in our range must pass 3 rounds of testing, and comes fully furnished with a well-equipped kitchen, all linen, and essential bathroom toiletries included. Make the most of the chilly season, and wrap up warm in a comfortable Winter Holiday Rental in Maidenhead. Reach out to our caring team of experts, who love nothing more than helping you discover the perfect home for your trip.

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