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.Read more

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 1027 holiday cottages available in September

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

7 nights from £254

1 bedroom, rural holiday cottage near Launceston, North Cornwall.


If you're looking for a peaceful break for two, you need look no further than Little Tregerry. Located down a country lane, in the heart of the Cornish countryside, this is the per...

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

7 nights from £254

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £260

1 bedroom, dog friendly cottage near Crantock, North Cornwall.


Tucked away in the rural hamlet of Trevilson, only a few miles inland from north Cornwall's breathtaking coastline, this delightful little cottage is the perfect bijou bolthole for...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £260

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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

7 nights from £268

1 bedroom self catering apartment near the beach in Seaview, Isle of Wight.


West Flatlet is situated right in the heart of Seaview village and is perfect for couples looking for a coastal break. This small but cosy and comfortable first floor flat sits at ...

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

7 nights from £268

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

7 nights from £275

1 bedroom, dog friendly holiday cottage near Penzance, West Cornwall.


Walkers and birdwatchers will enjoy the flora and fauna of the moors and wetlands surrounding Prospect Cottage, while both coastlines are less than a ten minute drive away. Soft bl...

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

7 nights from £275

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

7 nights from £275

1 bedroom, rural self catering cottage near Okehampton, North Devon.


What a tranquil spot this is amidst rolling fields and wooded valleys. Lower Hewton Farm dates back to the 16th Century and the cottage, which adjoins the main house, is welcoming ...

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

7 nights from £275

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

7 nights from £296

1 bedroom, dog friendly cottage near the beach near Portscatho.


Ideal for couples this detached, single-storey converted barn is located at Treluggan, a small country hamlet in the heart of the Roseland peninsula. There are some lovely coastal ...

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

7 nights from £296

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £297

1 bedroom, rural holiday cottage near St Ives, West Cornwall.


A hop, skip and a jump from wonderful beaches, galleries and restaurants, Bay Tree Barn is a delightful semi-detached cottage in a small hamlet on the edge of dramatic moorland, ju...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £297

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

7 nights from £297 *

2 bedroom, dog friendly holiday cottage near Looe, South Cornwall.


Tucked down a leafy lane with birdsong in the air, the rural tranquility of this pretty semi-detached cottage will delight those looking for a break from busy daily lives. Just...

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

7 nights from £297 *

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

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

7 nights from £300

1 bedroom, dog friendly holiday cottage near Falmouth, West Cornwall.


Buzzard’s Rise is an idyllic countryside retreat. Tucked away in a small hamlet, this contemporary barn conversion is great for exploring Cornwall or staying at home watching the w...

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

7 nights from £300

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £300

1 bedroom self catering apartment with sea views in Seaview, Isle of Wight


This gorgeous top floor one bedroom apartment has spectacular sea views over the rooftops across the Solent and is just a few minutes from Seaview village and the beach. Newly dec...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £300

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