Book Family Friendly Rentals in Winchcombe

We selected the 1330 homes worth renting in this location

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Home spotlights in Winchcombe

The Foxy Snug

The Foxy Snug

  • 14 guests

  • 5 bedrooms

Stanton, Broadway

This Grade II listed home dates back 400 years and is the perfect place to experience rural countryside grandeur. It’s a splendid home for celebrations and special occasions, with more than enough room for fourteen guests.

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.

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 Cotswolds Retreat

The Cotswolds Retreat

  • 6 guests

  • 3 bedrooms

Winchcombe, Cheltenham

Once the hayloft to one of the grandest homes in the Winchcombe area, this gorgeous barn conversion now presents a luxurious property in its own right. With characteristics from the 1880s, original features contrast beautifully with the high-standard furnishings and modern designs seen throughout the home.


We selected the top 3% holiday homes in Winchcombe Family Friendly Rentals

Explore the 1330 most perfect homes in our collection

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Most popular homes in Winchcombe

Sweetheart's Rest

Sweetheart's Rest

  • 4 guests

  • 2 bedrooms

Winchcombe, Cheltenham

Country Chimneys

Country Chimneys

  • 8 guests

  • 4 bedrooms

Winchcombe, Cheltenham

The Silver Knight

The Silver Knight

  • 12 guests

  • 5 bedrooms

Cheltenham, Gloucestershire

No Place I'd Rather Be

No Place I'd Rather Be

  • 2 guests

  • 1 bedrooms

Cheltenham, Gloucestershire

Lady Jane Grey & Princess Elizabeth

Lady Jane Grey & Princess Elizabeth

  • 4 guests

  • 2 bedrooms

Winchcombe, Cheltenham

A Royal Guest

A Royal Guest

  • 3 guests

  • 2 bedrooms

Winchcombe, Cheltenham

The Garden Room

The Garden Room

  • 6 guests

  • 2 bedrooms

Winchcombe, Cheltenham

The Orangery

The Orangery

  • 14 guests

  • 6 bedrooms

Greet, Cheltenham

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Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Winchcombe, Cheltenham, Gloucestershire, England, United Kingdom. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent Winchcombe Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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