Book Luxury Holiday Rentals in Winchcombe

Award-winning homes from £98

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Home spotlights in Winchcombe

Charm of the Cotswolds

Charm of the Cotswolds

  • 4 guests

  • 2 bedrooms

Winchcombe, Cheltenham

Tucked along a tree-lined lane on the outskirts of Winchcombe, this sweet cottage is as cosy as it looks. The red brick exterior exudes a simple country charm, but step inside and you'll be surprised by the sophisticated living space and contemporary comforts.

The Festival House

The Festival House

  • 2 guests

  • 1 bedrooms

Cheltenham, Gloucestershire

Put your out of office on and disconnect entirely at this cute little shepherd's hut near Winchcombe. With plenty of room for two, it sits in a quiet field with nothing but birdsong and the occasional whistle of a steam train in the distance.

The Crown & Anchor

The Crown & Anchor

  • 10 guests

  • 5 bedrooms

Cheltenham, Gloucestershire

If you fancy waking up to the sound of blackbirds singing in the trees, then this home is for you. This picture-perfect cottage is located in an idyllic corner of the Cotswolds and offers the perfect countryside escape for a large group looking for some fresh air and good times.

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 Holiday Rentals

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Most popular homes in Winchcombe

The Cotswolds Retreat

The Cotswolds Retreat

  • 6 guests

  • 3 bedrooms

Winchcombe, Cheltenham

Queen Mary

Queen Mary

  • 4 guests

  • 2 bedrooms

Winchcombe, Cheltenham

Queens & Castle

Queens & Castle

  • 6 guests

  • 2 bedrooms

Winchcombe, Cheltenham

The Gathering Place

The Gathering Place

  • 8 guests

  • 4 bedrooms

Bishops Cleeve, Gloucestershire

Second Nature

Second Nature

  • 2 guests

  • 1 bedrooms

Charlton Kings, Cheltenham

Cotswold Grace

Cotswold Grace

  • 2 guests

  • 1 bedrooms

Winchcombe, Cheltenham

The Crown & Chandelier

The Crown & Chandelier

  • 14 guests

  • 7 bedrooms

Winchcombe, Cheltenham

The Garden Room

The Garden Room

  • 6 guests

  • 2 bedrooms

Winchcombe, Cheltenham

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Winchcombe, Cheltenham, Gloucestershire, England, United Kingdom. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Winchcombe, Cheltenham, Gloucestershire, England, United Kingdom has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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