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 16 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. 

Select from 16 Somerset cottages available for September

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £230 *

2 bedroom holiday cottage near Dulverton, Somerset.


Cleveland Cottage has the advantage of a choice of two prices – for bookings by two or four guests. This very pretty cottage, on the edge of Exmoor National Park, a few miles from ...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £230 *

View
  • 50% off

    13 Sep 2019 - 20 Sep 2019

    £368.76 £184.50

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

7 nights from £349 *

2 bedroom holiday cottage near Ilminster, Somerset.


Flax Barn is located in the beautiful south Somerset village of Barrington, not far from the Dorset border. Barrington Court - one of several National Trust properties in the immed...

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

7 nights from £349 *

View
  • 20% off

    27 Sep 2019 - 4 Oct 2019

    £370.64 £296.51

Need more time? Reserve any cottage for up to 24 hours before booking.

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

7 nights from £360

1 bedroom, dog friendly holiday cottage near Dulverton, Somerset.


Sitting in the heart of Exmoor National Park, Week Cottage dates back to the 1690s and is all picture-book old world charm inside. A spacious boot-room, perfect for muddy boots (an...

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

7 nights from £360

View
  • 20% off

    20 Sep 2019 - 27 Sep 2019

    £449.82 £359.86

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £393

1 bedroom, dog friendly self catering cottage near Taunton, Somerset.


High up in Somerset's Quantock Hills, with some of the best walking this varied county has to offer right on the doorstep, Headford Farm Cottage is an excellent rural holiday base....

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £393

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £411

1 bedroom self catering cottage near Crewkerne, Somerset.


This really is the most beautifully designed bolthole for two. A romantic retreat with 'wow' factor in a traditional, rural hamlet setting in gorgeous south Somerset, close to the ...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £411

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

7 nights from £436

1 bedroom, dog friendly self catering 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 base...

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

7 nights from £436

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £437

Shepherds Hut with a hot tub sat on its own fishing pond near Weston-Super-Mare, Somerset.


The setting for this beautifully designed and fitted shepherd's hut is a celebration of what this kind of experience is all about. The gentle valley location is at the western edge...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £437

View
  • 10% off

    27 Sep 2019 - 4 Oct 2019

    £485.75 £437.18

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

7 nights from £462

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


At the heart of a farmstead in the Quantock Hills Area of Outstanding Natural Beauty, Duck's Puddle enjoys its own enclosed and private setting complete with a hot tub and little b...

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

7 nights from £462

Our guests rate us 4.8/5 on Feefo, the independent review site.

  • Sleeps 3
  • Regret no pets
  • Changeover Fri

7 nights from £384

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
  • Regret no pets
  • Changeover Fri

7 nights from £384

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £432

2 bedroom holiday cottage near Ilminster, Somerset.


Hayloft is in the heart of Barrington – a National Trust conservation village near the historic market town of Ilminster in south Somerset. This welcoming barn conversion is wit...

  • Sleeps 3 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £432

Loading more