Rent Luxury Holiday Cottages in Old Windsor

We selected the 336 homes worth renting in this location!

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Home spotlights in Old Windsor

Tea Up

Tea Up

  • 8 guests

  • 4 bedrooms

Hersham, Surrey

English charm and elegance await at this pretty seventeenth-century cottage in the countryside. Grade II listed but modernised to create a comfortable home with all modern conveniences, it's a beautiful place to relax with family and friends.

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.

What a Day for a Daydream

What a Day for a Daydream

  • 2 guests

  • 1 bedrooms

Hascombe, Godalming

Country escapes don’t get much more idyllic than this beautifully renovated studio barn in the village of Hascombe. Surrounded by two Areas of Oustanding Natural Beauty – the South Downs and the Surrey Hills – you’re in the perfect spot to enjoy countless walking trails and stunning scenery galore.

Mane Character

Mane Character

  • 4 guests

  • 2 bedrooms

Billingshurst, West Sussex

One of a collection of three cottages on a thirteen-acre working farm in West Sussex, this home is nowhere near as rustic as these details might suggest. Step behind the front door and you'll find an interior that's contemporarily styled with a few quirky touches.


We selected the top 3% holiday homes in Old Windsor Cottages

Explore the 336 most perfect homes in our collection

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Most popular homes in Old Windsor

Grain of Truth

Grain of Truth

  • 2 guests

  • 1 bedrooms

Leigh, Kent

The Saddler's Rooms

The Saddler's Rooms

  • 6 guests

  • 3 bedrooms

Hampshire, England

Forgotten Fields

Forgotten Fields

  • 2 guests

  • 1 bedrooms

Tetsworth, Thame

Chilterns Charm

Chilterns Charm

  • 6 guests

  • 3 bedrooms

Walter's Ash, Buckinghamshire

Stud Cottage

Stud Cottage

  • 2 guests

  • 1 bedrooms

Billingshurst, West Sussex

Hares & Haystacks

Hares & Haystacks

  • 4 guests

  • 2 bedrooms

Billingshurst, West Sussex

The Country Life

The Country Life

  • 6 guests

  • 3 bedrooms

Beckley and Stowood, Oxfordshire

The Equestrian

The Equestrian

  • 10 guests

  • 5 bedrooms

Chichester, West Sussex

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Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Old Windsor. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Old Windsor Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.

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