Rent Luxury Holiday Cottages in Winchcombe

We selected the 866 homes worth renting in this location

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Home spotlights in Winchcombe

Stone & Tapestry

Stone & Tapestry

  • 5 guests

  • 3 bedrooms

Winchcombe, Cheltenham

How’s a 15th-century castle that once housed King Charles I and Lady Jane Grey (to name a few) sound for a neighbour? It’s just footsteps away from this charming Cotswolds cottage –⁠ originally part of a paper mill on the vast estate.

Cotswold Grace

Cotswold Grace

  • 2 guests

  • 1 bedrooms

Winchcombe, Cheltenham

Only a mile from Winchcombe and Sudeley Castle, this pocket-sized hideaway is a perfect fit for two. We love how cosy and bright the living space is.

The Crown & Chandelier

The Crown & Chandelier

  • 14 guests

  • 7 bedrooms

Winchcombe, Cheltenham

Nestled into the Sudeley Castle Estate, fringing the charming village of Winchcombe, you'll find this Cotswold stone 18th Century farmhouse. Spread out over three floors, with a separate annex to spill into, this home is the perfect country escape for an extended family or group of friends.

Country Chimneys

Country Chimneys

  • 8 guests

  • 4 bedrooms

Winchcombe, Cheltenham

Oozing in medieval character with its sixteenth-century facade and original features throughout, Mercia hides a little secret behind its quirky front. You wouldn't expect it, yet a light-filled and contemporary entertaining space features at the back, with fabulous views of the Isbourne Valley and Sudeley Hill.


We selected the top 3% holiday homes in Winchcombe Cottages

Explore the 866 most perfect homes in our collection

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Most popular homes in Winchcombe

The Cotswolds Retreat

The Cotswolds Retreat

  • 6 guests

  • 3 bedrooms

Winchcombe, Cheltenham

A Cozy Retreat

A Cozy Retreat

  • 8 guests

  • 4 bedrooms

Winchcombe, Cheltenham

A Touch of Countryside

A Touch of Countryside

  • 6 guests

  • 3 bedrooms

Winchcombe, Cheltenham

Charm of the Cotswolds

Charm of the Cotswolds

  • 4 guests

  • 2 bedrooms

Winchcombe, Cheltenham

The Castle Laundry

The Castle Laundry

  • 12 guests

  • 6 bedrooms

Winchcombe, Cheltenham

The Old Forge

The Old Forge

  • 3 guests

  • 2 bedrooms

Winchcombe, Cheltenham

Willow Stream

Willow Stream

  • 4 guests

  • 2 bedrooms

Winchcombe, Cheltenham

A Royal Guest

A Royal Guest

  • 3 guests

  • 2 bedrooms

Winchcombe, Cheltenham

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Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Winchcombe, Cheltenham, Gloucestershire, 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 Winchcombe 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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