Book Luxury Holiday Lettings in Winchcombe

Award-winning homes from £98

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Home spotlights in Winchcombe

Queens & Castle

Queens & Castle

  • 6 guests

  • 2 bedrooms

Winchcombe, Cheltenham

Situated on a historic estate in the Cotswolds, this cottage grants you free entry to the on-site castle and gardens. As a former engine house, this home has heaps of character with traditional windows and wood beams, though the ceilings are low on the ground floor.

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.

The Gathering Place

The Gathering Place

  • 8 guests

  • 4 bedrooms

Bishops Cleeve, Gloucestershire

Gather your nearest and dearest for a comfortable stay at this retreat in Gloucestershire. Boasting contemporary interiors and views of the Cotswolds Hills, you'll feel instantly at home here.

Cotswolds Tranquility

Cotswolds Tranquility

  • 14 guests

  • 7 bedrooms

Winchcombe, Cheltenham

Originally a small dairy farm, this stone cottage has stood since it was built in 1685, and although it has undergone extensions and renovations, it has retained much of its charm and now makes for a cosy and inviting port of call for families looking to explore the Cotswolds. Set in the heart of Winchcombe, where walking trails will allow you to fully absorb the natural beauty of your surroundings, try the Sudeley Castle Circular for a more leisurely stroll before taking on any of the harder routes.


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

Explore the 1624 most perfect homes in our collection

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Most popular homes in Winchcombe

A Royal Guest

A Royal Guest

  • 3 guests

  • 2 bedrooms

Winchcombe, Cheltenham

Country Honey

Country Honey

  • 2 guests

  • 1 bedrooms

Cheltenham, Gloucestershire

Lord & Lady Admiral

Lord & Lady Admiral

  • 4 guests

  • 2 bedrooms

Winchcombe, Cheltenham

The Foxy Snug

The Foxy Snug

  • 14 guests

  • 5 bedrooms

Stanton, Broadway

The Bronze Knight

The Bronze Knight

  • 12 guests

  • 5 bedrooms

Cheltenham, Gloucestershire

The Crown & Chandelier

The Crown & Chandelier

  • 14 guests

  • 7 bedrooms

Winchcombe, Cheltenham

Country Chimneys

Country Chimneys

  • 8 guests

  • 4 bedrooms

Winchcombe, Cheltenham

Thatch House

Thatch House

  • 8 guests

  • 4 bedrooms

Gotherington, Cheltenham

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Frequently asked questions

Explore our selection of the finest luxury Holiday Lettings 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 Lettings for your trip.

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