Cottages for a five night break in The Cotswolds

Cottages for a five night break in The Cotswolds

We have an exclusive handpicked collection of luxury cottages available for you to enjoy that precious time away in The Cotswolds, so pick your next escape and get ready for a five night adventure. Read more

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

We have 19 cottages available in The Cotswolds available for five night breaks

2 Old Turnpike Cottages is a 2 bedroom, dog friendly self catering cottage with hot tub near Chipping Norton.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £804

2 Old Turnpike Cottages

5866

2 bedroom, dog friendly self catering cottage with hot tub near Chipping Norton.


Tucked away in the picturesque village of Middle Barton, just a short drive from Chipping Norton and the exclusive Soho Farmhouse lies this quintessential, dog-friendly Cotswold Co...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £804

The Yew Trees is a 2 bedroom dog friendly self catering cottage near Cheltenham.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1168

The Yew Trees

5862

2 bedroom dog friendly self catering cottage near Cheltenham.


This charming holiday cottage, nestled in the peaceful countryside just outside Cheltenham and the gorgeous Cotswolds, offers the perfect retreat for a tranquil getaway. Set in a r...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1168

Poppy Cottage is a 2 bedroom, dog friendly self catering cottage in Stratford-upon-Avon.
  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £726

Poppy Cottage

5850

2 bedroom, dog friendly self catering cottage in Stratford-upon-Avon.


Perfectly situated within walking distance of the historic town of Stratford-upon-Avon lies this stylish Victorian dwelling, Poppy Cottage. A beautiful characterful terraced home w...

  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £726

The Gallery is a 2 bedroom self catering cottage near Burford.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £530

The Gallery

5756

2 bedroom self catering cottage near Burford.


The Gallery is a super spacious, light and airy, semi-detached Cotswold barn. It has a fully equipped kitchen that leads through to an open plan sitting/dining-room, with a hugely ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £530

Oak Tree Cottage is a 2 bedroom self catering cottage near Burford.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £565

Oak Tree Cottage

5741

2 bedroom self catering cottage near Burford.


Oak Tree Cottage is a delightful semi-detached barn conversion and is nestled next to its neighbour, The Gallery (5756). They can be booked together for larger gatherings. The acco...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £565

Tower View is a 2 bedroom self catering cottage in Broadway.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £840

Tower View

5735

2 bedroom self catering cottage in Broadway.


Situated in the highly desirable Cotswold village of Broadway, Tower View, a charming two bedroom annexe, is a delightful cottage and makes the perfect couple's retreat. Meticulous...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £840

King John's Palace is a 6 bedroom self catering home near Burford
  • Sleeps 12 + 2 cots
  • Dogs welcome
  • Changeover Fri

From £608 per night

King John's Palace

5730

6 bedroom self catering home near Burford


Stay in style at King John's Palace, where kings and queens resided before you. A beautiful historic home close to the quintessential Cotswold town of Burford. This unique hidden g...

  • Sleeps 12 + 2 cots
  • Dogs welcome
  • Changeover Fri

From £608 per night

Weighbridge Barn

  • Sleeps 4 + 4 cots in 2 properties
  • Changeover Fri

7 nights from £1282

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Stable End is a 1 bedroom, dog friendly self catering cottage near Chippenham.
  • Sleeps 2 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £607

Stable End

5648

1 bedroom, dog friendly self catering cottage near Chippenham.


Located in Grittleton, a short drive from both Chippenham and Bath, just on the edge of the Cotswolds, an area of beautiful countryside and picturesque villages, come and discover ...

  • Sleeps 2 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £607

Weighbridge End is a 1 bedroom, dog friendly self catering cottage near Chippenham.
  • Sleeps 2 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £675

Weighbridge End

5647

1 bedroom, dog friendly self catering cottage near Chippenham.


This stunning barn located on the edge of the Cotswolds is a gem of a property just waiting to be discovered. Sympathetically converted with nods to its previous life as a working ...

  • Sleeps 2 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £675

Load more

A five night break in the UK allows you the opportunity to extend your short break just that little bit longer, giving you that much desired extra time to explore the area, unwind a little more and make the most of your time off. With gorgeous properties in Cornwall, Devon, Somerset, Dorset, Sussex and the Isle of Wight, you have plenty of options to choose from...