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 40 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 40 Somerset cottages available for September

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

7 nights from £408

Week Cottage

1636

1 bedroom, rural dog friendly 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 £408

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

7 nights from £429

Pitt Farm Cottage

3012

1 bedroom 17th Century 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 £429

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

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

7 nights from £435

Little Whitford

4542

1 bedroom, dog friendly cottage with views of alpacas near Taunton, Somerset.


Nestled in the Blackdown Hills, in an Area of Outstanding Natural Beauty, you will find super cute Little Whitford. All on one level, this small but perfectly formed bolthole for t...

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

7 nights from £435

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £435

Dieppy Farm Cottage

2788

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 £435

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

7 nights from £475

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 base...

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

7 nights from £475

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Thu

7 nights from £477

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 Area of Outstanding Natural Beauty. This stunning ancient landscape covers 100 square ki...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Thu

7 nights from £477

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £488

The Pump House

2098

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


Seize a totally unique opportunity and book a stay in this stunningly converted pump house on the Somerset/Dorset border, close to the dramatic beaches and clifftop walks of the Ju...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £488

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

7 nights from £499

Lamb's Tale Shepherd's Hut

3246

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

7 nights from £499

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

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

7 nights from £499

Duck's Puddle Shepherd's Hut

4026

Dog friendly shepherds hut with a 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 £499

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

7 nights from £511

Catford Cottage

4966

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


Tucked away in rural, unspoilt Exmoor, you will find Catford Cottage, a sweet bolthole just perfect for a couple and their four-legged friend looking to escape to the countryside. ...

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

7 nights from £511

Loading more