Book Luxury Holiday Rentals in Winchcombe

Award-winning homes from £98

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Home spotlights in Winchcombe

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.

A Cozy Retreat

A Cozy Retreat

  • 8 guests

  • 4 bedrooms

Winchcombe, Cheltenham

Located on the Sudeley Castle estate, just a short walk from the castle and its gardens, this quaint eighteenth-century cottage catches the eye with a beautiful Cotswold stone exterior. Positioned on the outskirts of historic Winchcombe, you'll benefit from incredible views of the village as well as easy access to plenty of cafes, shops and restaurants – this is an excellent base from which to explore the Cotswold's outstanding natural beauty.

The Old Forge

The Old Forge

  • 3 guests

  • 2 bedrooms

Winchcombe, Cheltenham

Set within the grounds of a 15th-century castle and within walking distance of the Cotswold's town of Winchcombe, the setting of this dog-friendly cottage is a knockout. Inside, the traditional interiors are befitting of this period home, and the wooden deck outside is a nice touch for evening drinks.

A Royal Guest

A Royal Guest

  • 3 guests

  • 2 bedrooms

Winchcombe, Cheltenham

Nestled in the grounds of a 15th-century castle, and fringing the charming village of Winchcombe, this dog-friendly cottage is one-of-a-kind. Make sure to discover the fascinating history of the estate, which you’ll have complimentary access to.


We selected the top 3% holiday homes in Winchcombe Holiday Rentals

Explore the 23 most perfect homes in our collection

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Most popular homes in Winchcombe

A Touch of Countryside

A Touch of Countryside

  • 6 guests

  • 3 bedrooms

Winchcombe, Cheltenham

The Crown & Chandelier

The Crown & Chandelier

  • 14 guests

  • 7 bedrooms

Winchcombe, Cheltenham

Hilltop Tranquility

Hilltop Tranquility

  • 7 guests

  • 4 bedrooms

Winchcombe, Cheltenham

By the Forge

By the Forge

  • 4 guests

  • 2 bedrooms

Winchcombe, Cheltenham

Charm of the Cotswolds

Charm of the Cotswolds

  • 4 guests

  • 2 bedrooms

Winchcombe, Cheltenham

Cotswolds Tranquility

Cotswolds Tranquility

  • 14 guests

  • 7 bedrooms

Winchcombe, Cheltenham

Queens & Castle

Queens & Castle

  • 6 guests

  • 2 bedrooms

Winchcombe, Cheltenham

Stone & Tapestry

Stone & Tapestry

  • 5 guests

  • 3 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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