Luxury Holiday Cottages for September

September is around the corner and a holiday in a self-catering cottage is beckoning. With the last of the summer sunshine, warm sea temperatures from months of hot weather and the crowds starting to dwindle, September is a fantastic time to enjoy a holiday in a home-from-home. Solo retreat, family holiday or gathering with friends, our cottages provide an idyllic base from which to enjoy a perfect getaway.

The beaches are inviting, the sea's had all summer to warm up and the schools have gone back, so make the most of quieter scenes still drenched in warm sunlight and give yourselves something to smile about. With our range of self-catering cottages, guests of all ages will settle straight in. Whether you are looking for a cottage nestled in the heart of lush countryside, a seaside sanctuary affording spectacular sea views or a town hub offering access to lots of local amenities, we will help you pave the way to your dream holiday this September. Offering a wide range of facilities, from enclosed gardens with barbecues, to homes with private swimming pools to properties with games rooms for kids, let your imagination run wild thinking about all the possibilities for your holiday in a Classic cottage. 

Holiday Cottages for September

At Classic Cottages we pride ourselves on marketing only the finest quality self-catering accommodation around. Combining the highest level of customer service with luxury cottages, we want your whole holiday to be the best it can be. Browse our portfolio for September and find your favourite now. 

We have 939 holiday cottages available in September

2 bedroom, dog-friendly, converted barn near Exmoor National park


Westlake Barn is in a lovely rural setting, within easy reach of the popular market town of Dulverton, at the heart of Exmoor National Park, as well as the wide sandy surfing beach...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

Price per week £436 - £585

2 bedroom holiday cottage near Ilminster, Somerset.


Situated in the National Trust conservation village of Barrington, Flax Barn is one of four properties created from a group of historic barns, and is a comfortable, well placed bas...

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

Price per week £436 - £597

Our property managers are local experts who handpick perfect places to stay.

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

Price per week £438 - £589

3 bedroom, dog friendly cottage near the beach near Lamorna Cove.


The lush Lamorna valley lies just one mile away from this comfortable single-storey property which, as it is all on one level, is suitable for guests with limited mobility. St Loy ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £439 - £540

2 bedroom, dog friendly cottage near Launceston.


Set in tranquil countryside, Carzantic Chapel Barn is a charming granite cottage dating back to the 1800s, its south-facing patio basks in sun most of the day and is the perfect sp...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

Price per week £439 - £572

2 bedroom holiday cottage near the beach in St Mawes, South Cornwall.


Steps lead up to this gorgeous converted sail loft set close to the centre of St Mawes, famous for its quaint harbour and delightful passenger ferry to Falmouth. Tucked away and ju...

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

Price per week £440 - £534

2 bedroom dog-friendly self catering cottage near the beach near Portloe.


Dolphin Cottage is a cosy mid-terrace former coastguard’s cottage, situated on the edge of the picturesque fishing village of Portloe, with sea views from the terrace. The bijou co...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

Price per week £441 - £568

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

Price per week £441 - £592

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

2 bedroom holiday apartment near the beach in Hayle, West Cornwall.


Within a few minutes' walk of Hayle harbour, with its quirky shops and numerous eateries, or a slightly longer stretch to three miles of golden sands; this sumptuously furnished fi...

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

Price per week £441 - £592

2 bedroom, dog friendly holiday cottage near Hayle, West Cornwall.


With its sunny, sheltered enclosed back garden with your own private hot tub, detached Sunset Barn is a beautifully presented open plan cottage. Set on a small and peaceful smallho...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

Price per week £441 - £561

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