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 37 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 37 Somerset cottages available for September

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

7 nights from £348 *

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 £348 *

View
  • 20% off

    21 Dec 2018 - 28 Dec 2018

    £550.40 £440.00

  • 20% off

    28 Dec 2018 - 4 Jan 2019

    £688.00 £550.40

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

7 nights from £359

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 t...

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

7 nights from £359

We are Gold accredited with the Green Tourism Business Scheme.

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

7 nights from £379

1 bedroom self catering cottage near Dulverton, Somerset.


This beautifully refurbished 17th Century cottage has been designed as a comfortable bolthole for two, a little tucked away base on the edge of beautiful Exmoor National Park. P...

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

7 nights from £379

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £393

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


Dieppy Farm Cottage is a delightful bolthole in the peaceful village of Skilgate, on the edge of Exmoor's stunning National Park. This most welcoming single-storey cottage has a hu...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £393

  • 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 £431

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


This delightful traditional stone cottage is a tranquil village bolthole near Glastonbury, just south of Somerset's stunning Mendip Hills, with their spectacular landscapes and dra...

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

7 nights from £431

View
  • 15% off

    14 Dec 2018 - 21 Dec 2018

    £627.48 £532.95

  • 20% off

    21 Dec 2018 - 28 Dec 2018

    £627.48 £501.60

  • Sleeps 2
  • Dogs welcome
  • Changeover Sat

7 nights from £439

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


This unique pied-a-terre, close to the Somerset/Dorset border not far from the Jurassic Coast, stands in its own private wildlife meadow. Perfect for couples, this idyllic retre...

  • Sleeps 2
  • Dogs welcome
  • Changeover Sat

7 nights from £439

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

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

7 nights from £450

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 £450

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

7 nights from £465

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 £465

Loading more