Rent Luxury Holiday Cottages in Old Windsor

We selected the 336 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

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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.

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.

Stud Cottage

Stud Cottage

  • 2 guests

  • 1 bedrooms

Billingshurst, West Sussex

Set on a farm in West Sussex, this charming cottage is the perfect couple’s retreat or solo getaway. The interiors are bright and fun, with pops of block colour punctuating each room.


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

Cotswold Spirit

Cotswold Spirit

  • 4 guests

  • 2 bedrooms

Witney, Oxfordshire

Grain of Truth

Grain of Truth

  • 2 guests

  • 1 bedrooms

Leigh, Kent

Strong and Stables

Strong and Stables

  • 4 guests

  • 2 bedrooms

Thakeham, Pulborough

The Bread Oven

The Bread Oven

  • 4 guests

  • 2 bedrooms

Chipping Norton, Oxfordshire

Forgotten Fields

Forgotten Fields

  • 2 guests

  • 1 bedrooms

Tetsworth, Thame

Cottage Blooms

Cottage Blooms

  • 8 guests

  • 4 bedrooms

Chipping Norton, Oxfordshire

Chilterns Charm

Chilterns Charm

  • 6 guests

  • 3 bedrooms

Walter's Ash, Buckinghamshire

Harpsden Haven

Harpsden Haven

  • 10 guests

  • 5 bedrooms

Harpsden, Henley-on-Thames

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Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Old Windsor, England, United Kingdom. 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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