September Holidays in Somerset

September Holidays in Somerset

Squeeze out the last drops of summer and head to Somerset for an unforgettable holiday. Enjoy the September sunshine illuminating Somerset's beautiful landscapes and spend your days making the most of the late summer vibes. Then, when you are ready to turn in, return to your own slice of paradise in a luxury self-catering retreat. Read more

If you are not quite ready to let summer go yet, book yourself a September holiday in Somerset. Last-minute or planned well in advance, a September getaway in Somerset will let you do your summer justice and leave you feeling relaxed and revived. Whether you are looking for a one-bed retreat, dog-friendly holiday cottage or big house with space enough for all the family and friends too, we will help you find the right cottage for you. With every one of our holiday cottages personally inspected and carefully selected onto our books, we make sure you can enjoy the best of the best. Browse our 35 cottages available for a September break in Somerset and let the good times commence. Your holiday with Classic Cottages will be so good you'll wish you could do it twice. 

Isle of Wight Ferry Booking Our exclusive ferry discounts will make your island trip with Classic plain sailing.

Select from 35 Somerset cottages available for September

Lamb's Tale Shepherd's Hut is a Dog friendly shepherds hut with a hot tub, near Bridgwater in Somerset.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

From £92 per night

Lamb's Tale Shepherd's Hut

3246

Dog friendly shepherds hut with a hot tub, near Bridgwater in Somerset.


Somerset's Quantock Hills – a nine and a half thousand acre Area of Outstanding Natural Beauty – rise up just behind the farm setting for this beautifully crafted, bespoke Shepherd...

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

From £92 per night

Bashford Lodge is a 3 bedroom lodge with far reaching countryside views near Taunton, Somerset.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £575 *

Bashford Lodge

3226

3 bedroom lodge with far reaching countryside views near Taunton, Somerset.


This fabulous Somerset property has panoramic views that will take your breath away. Set on the edge of the Quantock Hills National Landscape, in the very picturesque village of We...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £575 *

Andrew’s House is a 3 bedroom cottage in Dulverton, Somerset.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £720

Andrew’s House

2932

3 bedroom cottage in Dulverton, Somerset.


This spacious period house is on the edge of Dulverton, the gateway to Exmoor National Park, seconds from the riverside walk into this lovely little town. Andrew's House is on t...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £720

Kingham Cottage is a 2 bedroom, dog friendly cottage near Bath, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £635

Kingham Cottage

2928

2 bedroom, dog friendly cottage near Bath, Somerset.


This 'best of all boltholes' is just a couple of miles outside the wonderful city of Bath and yet in a rural setting with panoramic valley views and a deep sense of peacefulness. ...

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

7 nights from £635

Ashey Barn is a 1 bedroom, rural, dog friendly cottage near Wells, Somerset.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £600

Ashey Barn

2787

1 bedroom, rural, dog friendly cottage near Wells, Somerset.


This converted single-storey barn is in a peaceful, rural position on the edge of Somerset’s Mendip Hills, within easy reach of Bath, Bristol and Wells. Ashey Barn is a perfect bas...

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

7 nights from £600

Headford Farm Cottage is a 1 bedroom rural dog friendly cottage near Taunton, Somerset.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Thu

7 nights from £549

Headford Farm Cottage

2809

1 bedroom rural dog friendly cottage near Taunton, Somerset.


Headford Farm Cottage is on the edge of a rural hamlet, high up in Somerset's Quantock Hills National Landscape. This stunning ancient landscape covers 100 square kilometres of oak...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Thu

7 nights from £549

We’ve been raising the standards of self catering holidays since 1977.

Brookside Cottage is a 2 bedroom thatched cottage near Nether Stowey, Somerset.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £758

Brookside Cottage

2638

2 bedroom thatched cottage near Nether Stowey, Somerset.


In a beautiful wooded valley in the east Quantock Hills National Landscape, Brookside Cottage is an idyllic getaway. This thatched semi-detached property lies within a conservat...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £758

The Old Barn at Cherry May Farm is a 2 bedroom, rural holiday cottage with hot tub near Glastonbury, Somerset.
  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £888

The Old Barn at Cherry May Farm

2550

2 bedroom, rural holiday cottage with hot tub near Glastonbury, Somerset.


The Old Barn at Cherry May Farm, on the edge of the unique Somerset Levels, is a winner of the West Somerset Council 'Excellence in Building Awards' that embraces the very best asp...

  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £888

Lane Cottage is a 1 bedroom, dog friendly cottage in Dulverton, Somerset.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £431

Lane Cottage

2482

1 bedroom, dog friendly cottage in Dulverton, Somerset.


Lane Cottage is a perfect Exmoor bolthole, tucked into a little square in the centre of the lovely market town of Dulverton. The cottage is really cosy, with a multi-burner in t...

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

7 nights from £431

Birch House Studio is a 2 bedroom, rural holiday cottage near Wellington, South Devon.
  • Sleeps 3
  • No pets
  • Changeover Fri

7 nights from £507

Birch House Studio

2460

2 bedroom, rural holiday cottage near Wellington, South Devon.


This beautifully presented single-storey property is perfect for exploring the unspoilt Blackdown Hills, the stunning Jurassic Coast – both designated Areas of Outstanding Natural ...

  • Sleeps 3
  • No pets
  • Changeover Fri

7 nights from £507

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