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 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £425 *

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


This gorgeous Victorian cottage is an absolute delight; updated with gentle sympathy to offer the modern necessities of central heating, drench-head shower and a granite-topped kit...

  • Sleeps 5 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £425 *

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

7 nights from £427

1 bedroom, dog friendly self catering cottage in Widecombe, Dartmoor.


Ned's is the perfect dog-friendly Dartmoor bolthole. Named after a local character who lived in the cottage and who played the fabled ‘Uncle Tom Cobley’ for many years at the Widec...

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

7 nights from £427

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

7 nights from £428

1 bedroom, rural self catering cottage near Penzance, West Cornwall.


A sign that greets you on arrival states ‘Seas the Day’ and this is the place in which to do it. The Duck House is a gorgeous, contemporary, single-storey dwelling with all mod-con...

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

7 nights from £428

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £430

1 bedroom, dog friendly holiday cottage near Tavistock, Dartmoor.


In an Area of Outstanding Natural Beauty just a mile from Dartmoor, The Wool Shed is a single-storey property found in Lower Chaddlehanger. Furnished and decorated in a contemporar...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £430

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £431

1 bedroom, rural cottage near the beach in Penzance, West Cornwall.


Pretty Love Lane Cottage is set down a quiet narrow lane on the outskirts of Penzance within the grounds of the Owners' home. Penzance town centre and the fishing village of Newlyn...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £431

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £431

1 bedroom, dog friendly shepherds hut with own fishing lake near Exeter.


A few miles outside the Roman city of Exeter, a few miles inland from the east Devon Jurassic Coast, and many miles away from the fast pace of everyday life, sits a delightful shep...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £431

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

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £431

Gorgeous Shepherds Hut sleeping two near St Ives, West Cornwall.


Found in a tranquil and unspoilt part of far west Cornwall, approached by lanes full of wildflowers in the spring and summer, this gorgeous hideaway is set in its own sheltered and...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £431

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £431

1 bedroom, dog friendly shepherds hut with wood-fired hot tub near Exeter.


This beautifully presented shepherd's hut is as much a part of the landscape here as the ancient oak which gives it its name. The two stand side-by-side at the top of a gently slop...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £431

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

7 nights from £431

Gorgeous shepherds hut sleeping 2 near Lyme Regis, South Devon.


The location high above the Axe Valley as it heads to the Jurassic Coast just a few miles away could not be more magical. Easy to reach, yet off the beaten track for the last adven...

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

7 nights from £431

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

7 nights from £431

1 bedroom holiday cottage with sea views near Dawlish, South Devon.


This delightful and spacious detached cottage provides the perfect getaway location for two. Furnished and equipped to a very high standard, The Apple House offers you a wonderful ...

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

7 nights from £431

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