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 20 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 20 Somerset cottages available for September

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

7 nights from £404

Little Whitford

4542

1 bedroom, dog friendly self catering cottage 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 £404

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £453

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 £453

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

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Thu

7 nights from £459

Headford Farm Cottage

2809

1 bedroom, dog friendly self catering 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 £459

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

7 nights from £466

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 £466

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

7 nights from £466

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 £466

  • Sleeps 3
  • Regret no pets
  • Changeover Fri

7 nights from £403

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
  • Regret no pets
  • Changeover Fri

7 nights from £403

  • Sleeps 3 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £428

Orchard Barn

3289

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


Orchard Barn is a stone's throw from the stunning Quantock Hills Area of Outstanding Natural Beauty; 9,500 acres of open moorland, deep wooded valleys and panoramic views. The sing...

  • Sleeps 3 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £428

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £441

Hayloft

2403

2 bedroom dog friendly holiday cottage near Ilminster, Somerset.


Hayloft is in the heart of Barrington near the historic market town of Ilminster in south Somerset. This welcoming barn conversion is within a small group of historic barns and ...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £441

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £772 *

The Watermill

2703

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


Set in the courtyard of an original farmstead in a scenic location, within easy reach of Exmoor National Park’s open moorlands and the lovely market towns of Dulverton and Bampton,...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £772 *

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £441

Oak Tree Barn

3288

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


Oak Tree Barn is a family-friendly and dog-friendly barn conversion with a wonderful level garden in a peaceful setting on the edge of the unspoilt village of Thurloxton, in the fo...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £441

Loading more