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 959 holiday cottages available in September

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £575

4 bedroom holiday cottage near the sea in Boscastle, North Cornwall.


Anyone with a romantic yearning for a harbourside haven will be thrilled with Penally Cottage. Full of character (with the occasional low beam!), this end of terrace cottage wi...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £575

View
  • 20% off

    30 Mar 2019 - 6 Apr 2019

    £547.56 £438.05

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £575

3 bedroom, dog friendly apartment near the beach in Seaview, Isle of Wight.


This lovely three bedroom ground floor apartment is within a few minutes’ walk to the beach and Seaview village with the added bonus of a mature garden with outdoor seating. The ne...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £575

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

  • Sleeps 6
  • Regret no pets
  • Changeover Sat

7 nights from £575

3 bedroom self catering cottage with sea views in Cowes, Isle of Wight.


Right in the heart of the bustling sailing town of Cowes, 9 Crown Court offers great accommodation with a stunning roof terrace boasting uninterrupted views across the rooftops to ...

  • Sleeps 6
  • Regret no pets
  • Changeover Sat

7 nights from £575

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £578

3 bedroom, dog friendly cottage with sea views in Marazion, Cornwall.


Hidden down a traffic-free lane in Marazion, Cliff House is one of the closest houses to St Michael's Mount – the beach and coast path are practically on its doorstep. Peace and qu...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £578

View
  • 20% off

    23 Mar 2019 - 30 Mar 2019

    £546.92 £437.54

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £583 *

4 bedroom, rural cottage near the sea near Falmouth, South Cornwall.


Less than a mile from the famous Pandora Inn at beautiful Restronguet Creek and set in a wonderfully tranquil countryside location, Dowstall Barn is perfect for relaxing and enjoya...

  • Sleeps 8 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £583 *

View
  • 20% off

    22 Mar 2019 - 29 Mar 2019

    £555.66 £444.53

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

7 nights from £583

3 bedroom, dog friendly holiday cottage near the beach in Yarmouth, Isle of Wight.


Rose Villa is a beautifully appointed home in the heart of the village of Yarmouth. It would ideally suit a family or a group of friends traveling together. This spacious prope...

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

7 nights from £583

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

7 nights from £584

3 bedroom, dog friendly cottage near Port Isaac, North Cornwall.


Kear Cottage is an absolute peach! Located less than six miles from the stunning beaches and fishing villages on the north Cornish coast, it sits in the most idyllic setting opposi...

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

7 nights from £584

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £585

3 bedroom cottage near Portscatho, South Cornwall.


Trevow is idyllically situated facing eastwards over fields towards the sea at Rosevine, only five minutes' walk from the National Trust coastal path and sandy beach at Porthcurnic...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £585

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

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £586

3 bedroom cottage with sea views near Portscatho, South Cornwall.


With lovely sea views to Gull Rock and Gerrans Bay, especially from the master bedroom, Tamarisk is a spacious detached dormer bungalow. Renovated to a high standard, the property ...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £586

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £586

3 bedroom cottage with sea views in The Lizard, West Cornwall.


First impressions of this beautifully presented, detached single-storey cottage is of light, openness and stylish comfort. Set on the quiet outskirts of Lizard, the most southerly ...

  • Sleeps 6 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £586

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