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 33 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 33 Somerset cottages available for September

  • 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

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

7 nights from £489

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 £489

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  • 10% off

    29 Mar 2019 - 5 Apr 2019

    £420.50 £378.45

  • 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

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

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

7 nights from £421

2 bedroom holiday cottage near Taunton, Somerset.


Court Cottage lies at the heart of West Monkton, a peaceful Somerset village, below the beautiful Quantock Hills, an Area of Outstanding Natural Beauty, above the Vale of Taunton t...

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

7 nights from £421

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

7 nights from £436

2 bedroom self catering cottage with sea views in Minehead, Somerset.


Set back from the seafront esplanade with fantastic sea views and just steps from the South West Coast Path, Grade II Listed 1 Coastguard Cottages is the perfect location for a fam...

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

7 nights from £436

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £438

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


Manor Farm Lodge is the ideal base for exploring the fascinating area around the Somerset/Dorset border, and is within easy reach of the stunning Jurassic Coast at Lyme Regis. This...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £438

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £441

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


Oak Tree Barn is a family-friendly and dog-friendly barn conversion in a peaceful setting on the edge of the unspoilt village of Thurloxton, in the foothills of the Quantock Hills ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £441

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £460

2 bedroom, dog friendly holiday cottage near Taunton, Somerset.


Knights Barton is in a peaceful setting on the edge of the village of Halse, one of the prettiest in Somerset, between the Quantock Hills and Exmoor. This top quality, deceptive...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £460

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

7 nights from £473

2 bedroom thatched holiday cottage near Nether Stowey, Somerset.


In a beautiful wooded valley in the east Quantock Hills Area of Outstanding Natural Beauty, Brookside Cottage is an idyllic getaway. This thatched semi-detached property lies wi...

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

7 nights from £473

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

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