Book Luxury Monthly Rentals in Old Windsor

We selected the 5540 homes worth renting in this location!

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Home spotlights in Old Windsor

Pink Slice

Pink Slice

  • 6 guests

  • 2 bedrooms

Windsor, Berkshire

A fifteen-minute stroll from the shop-lined High Street, you'll find Windsor Castle beyond – a must-see fortress for royal family fans. Fancy afternoon tea at a nearby racecourse?

The Belgian Ambassador

The Belgian Ambassador

  • 8 guests

  • 4 bedrooms

Bray Civil Parish, Berkshire

Built back in 1861, this home was originally a vicarage to an adjacent church, which was demolished in the 1960s — there's a still small cemetery at the front of the property. Things have certainly moved on since the middle of the nineteenth century and the interior is a triumph of modern design.

The Eclectic Hidden Cottage

The Eclectic Hidden Cottage

  • 5 guests

  • 3 bedrooms

Esher, Surrey

This Eclectic Hidden Cottage is the perfect place to relax and unwind. The cottage is warm and inviting, with dark wood flooring, light soft furnishings, and original antique pieces.

Winkfield Woods

Winkfield Woods

  • 3 guests

  • 1 bedrooms

Cranbourne, Windsor

This cosy guest house is in the heart of Winkfield. It’s a great base for discovering all there is to see and do nearby, including visiting Windsor and Eton, enjoying days out at Ascot, and treating the kids to a Legoland adventure.


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

Explore the 5540 most perfect homes in our collection

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Most popular homes in Old Windsor

The Whistler

The Whistler

  • 7 guests

  • 4 bedrooms

Old Windsor, Berkshire

The Saddler's Rooms

The Saddler's Rooms

  • 6 guests

  • 3 bedrooms

Hampshire, England

Eton Oasis

Eton Oasis

  • 6 guests

  • 2 bedrooms

Eton, Windsor

Nom de Plume

Nom de Plume

  • 9 guests

  • 5 bedrooms

Dorney, Buckinghamshire

Green on My Mind

Green on My Mind

  • 10 guests

  • 5 bedrooms

Shere, Guildford

The Great British Retreat

The Great British Retreat

  • 18 guests

  • 9 bedrooms

Bray Civil Parish, Berkshire

Royal Next Door

Royal Next Door

  • 6 guests

  • 3 bedrooms

Windsor, Berkshire

The Windsor Crown

The Windsor Crown

  • 5 guests

  • 3 bedrooms

Old Windsor, England

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Old Windsor, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Old Windsor Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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