Book Luxury Holiday Rentals in Winchcombe

Award-winning homes from £98

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Home spotlights in Winchcombe

Lady Jane Grey & Princess Elizabeth

Lady Jane Grey & Princess Elizabeth

  • 4 guests

  • 2 bedrooms

Winchcombe, Cheltenham

This period cottage, set within the grounds of a 15th-century castle fringing Winchcombe, has some impressive royal connections. Named after Queen Elizabeth I, who favoured the castle as a young princess, there’s heaps of history to uncover here.

The Silver Knight

The Silver Knight

  • 12 guests

  • 5 bedrooms

Cheltenham, Gloucestershire

This home is something else, so where do we even begin? Set between Stow and Cheltenham, it’s nestled to the edge of a wooded Cotswolds hamlet with beautiful views of surrounding greenery and grassland.

Foxglove House

Foxglove House

  • 10 guests

  • 6 bedrooms

Cheltenham, Gloucestershire

When you stay at this idyllic Grade-II listed home in the Cotswolds, you’ll be able to relax in the enclosed garden with its picturesque surroundings. There are views of the countryside and borders packed with flowers.

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

Explore the 1634 most perfect homes in our collection

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Most popular homes in Winchcombe

The Old Forge

The Old Forge

  • 3 guests

  • 2 bedrooms

Winchcombe, Cheltenham

Hilltop Tranquility

Hilltop Tranquility

  • 7 guests

  • 4 bedrooms

Winchcombe, Cheltenham

The Canopy of the Forest

The Canopy of the Forest

  • 4 guests

  • 3 bedrooms

Winchcombe, Cheltenham

Snowshill Style

Snowshill Style

  • 6 guests

  • 3 bedrooms

Snowshill, Gloucestershire

The Cottage Green

The Cottage Green

  • 6 guests

  • 3 bedrooms

Alderton, Tewkesbury

A Royal Guest

A Royal Guest

  • 3 guests

  • 2 bedrooms

Winchcombe, Cheltenham

The Crown & Chandelier

The Crown & Chandelier

  • 14 guests

  • 7 bedrooms

Winchcombe, Cheltenham

Oliver Cromwell

Oliver Cromwell

  • 4 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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