Rent Luxury Holiday Cottages in Old Windsor

We selected the 0 homes worth renting in this location

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Home spotlights

Cottage Hideaway

Cottage Hideaway

  • 4 guests

  • 2 bedrooms

Shipton-under-Wychwood, Oxfordshire

If you’re longing for country charm, this cottage in the Cotswolds could be the holiday home for you. It sits in an Area of Outstanding Natural Beauty in Shipton-under-Wychwood, close to other chocolate box villages including Stow-on-the-Wold, Moreton-in-Marsh, and Chipping Norton.

Tippin' Cottage

Tippin' Cottage

  • 2 guests

  • 1 bedrooms

Lower Slaughter, Cheltenham

Situated in the Cotswold village of Lower Slaughter, just off a road once named Britain’s most romantic street, this home is perfect for a couples retreat. Filled to the brim with original features, you’ll find everything you need for a relaxing stay here.

Charing Charm

Charing Charm

  • 10 guests

  • 5 bedrooms

Charing, Kent

This enchanting home is perfect for large family groups. The home is split between the main house – which sleeps ten – and a cosy cottage for two, ideal for a couple seeking a touch more privacy.

The Cottage Soul

The Cottage Soul

  • 20 guests

  • 10 bedrooms

Peterborough, England

This old dairy, set on the Burghley Estate, is a peaceful getaway for large groups and makes a pretty picture for small celebrations. Throughout the restoration of the dairy and its conversion into cottages, an emphasis remained on the history of this building, and plenty of the original features remain to make this a charming and comfortable stay.


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

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Most popular homes

The Toadstool

The Toadstool

  • 6 guests

  • 3 bedrooms

King's Bromley, Burton-on-Trent

Babbling Brooks

Babbling Brooks

  • 8 guests

  • 3 bedrooms

Ramsbottom, Bury

Fantastic Beasts

Fantastic Beasts

  • 8 guests

  • 5 bedrooms

Walmer, Kent

Faerie World

Faerie World

  • 2 guests

  • 1 bedrooms

Bath, Somerset

A Little Peach

A Little Peach

  • 2 guests

  • 1 bedrooms

Wimborne Saint Giles, Wimborne

Serving Up Style

Serving Up Style

  • 4 guests

  • 2 bedrooms

Wimborne Saint Giles, Wimborne

Tea Up

Tea Up

  • 8 guests

  • 4 bedrooms

Hersham, Surrey

Dovesong

Dovesong

  • 6 guests

  • 3 bedrooms

Weston Subedge (DET), Gloucestershire

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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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