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. 

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 39 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 39 Somerset cottages available for September

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

Price per week £341 - £572 *

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* Includes 20% off for parties up to 2 + cot.

  • 20% off

    3 Aug 2018 - 10 Aug 2018

    £688.00 £550.40

1 bedroom, dog friendly self catering cottage in Dulverton, Somerset.


Lane Cottage is a perfect Exmoor bolt-hole, 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 the ...

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

Price per week £369 - £505

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

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 Sat

Price per week £392 - £509

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

Price per week £403 - £525

1 bedroom self catering cottage near Wells, Somerset.


The Hayloft is a wonderfully tranquil bolt-hole for two in a rural edge of village setting near the beautiful Cathedral City of Wells. Close to the incredible RSPB wildlife sanctua...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

Price per week £409 - £559

1 bedroom self catering cottage near Taunton, Somerset.


This cottage is the perfect base for exploring the ancient Somerset Levels and the very special RSPB sites for which this county is renowned. There are lovely walks here and Fig Tr...

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

Price per week £429 - £557

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


This delightful little Grade II Listed stone cottage is in the heart of the village of Pilton, near Glastonbury. 2 Batch Cottages, in Bread Street, was likely to have been one of t...

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

Price per week £431 - £590

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

Price per week £452 - £587

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  • 10% off

    3 Aug 2018 - 10 Aug 2018

    £675.00 £607.50

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

Shepherds Hut with hot tub, dog friendly near Bridgwater, 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

Price per week £452 - £587

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. The Barn is a perfect base f...

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

Price per week £459 - £596

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