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 1004 holiday cottages available in September

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

7 nights from £403

1 bedroom, dog friendly self catering cottage near Sherborne, Dorset.


This cosy, compact, delightful bolthole for two is set in a wonderfully tranquil hamlet in north Dorset with village shops and a choice of two pubs within two miles. Built in lo...

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

7 nights from £403

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

7 nights from £404 *

4 bedroom, dog friendly cottage near Mevagissey, South Cornwall.


This wonderfully homely farmhouse is found in a tranquil rural setting at the end of a private lane. There are countryside views and an enclosed south-facing garden, and guests can...

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

7 nights from £404 *

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £404

1 bedroom, rural self catering cottage near Looe, South Cornwall.


Wind your way along country lanes to this truly delightful retreat that is just the tonic for those looking to enjoy precious time together and escape the humdrum of everyday life....

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £404

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

7 nights from £405 *

Luxury shepherds hut with hot tub and fabulous views in the countryside near Ottery St Mary, Devon


The stunning World Heritage Jurassic Coast stretches right into east Devon and, just a few miles inland from magical Budleigh Salterton, a dedicated meadow at Knightstone Farm awai...

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

7 nights from £405 *

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £405

1 bedroom holiday cottage near the beach in St Ives, West Cornwall.


The perfect retreat for walkers and couples, this compact semi-detached cottage is set on a steep wooded lane which is a three minute walk to Carbis Bay beach and its amenities. Fo...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £405

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

7 nights from £406

1 bedroom dog-friendly holiday cottage nr St Neot, south Cornwall


Set in the midst of an Area of Outstanding Natural Beauty and perfect for enthusiastic walkers, this comfortably spacious retreat for two is ideally situated for exploring the myst...

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

7 nights from £406

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

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

7 nights from £406

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


Just inland from the glorious south coast footpaths that meander past Whitsand, Looe and Lantivet bays, this comfortable, stylish and beautifully presented cottage is the perfect b...

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

7 nights from £406

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

7 nights from £407 *

Cabin and Safari Tent sleeping up to 6 near St Mawes, South Cornwall.


What could be more enchanting than this beautifully styled cabin with its carved African dark wood furniture enhanced by flashes of gorgeously bright colour in the rugs, cushions a...

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

7 nights from £407 *

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

7 nights from £407

1 bedroom, dog friendly holiday cottage near St Ives, West Cornwall.


This enchanting little gem nestles in a peaceful valley equidistant from St Ives and Penzance. Peace and plenty are assured in the private garden of your converted 18th Century sta...

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

7 nights from £407

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £410

1 bedroom, dog friendly self catering cottage near Bridport, Dorset.


Badgers Cottage, a snug semi-detached cottage for two, is set in a farmyard, beautifully converted from an 18th Century stone barn. All on one level, the open plan design gives a w...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £410

Loading more