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 919 holiday cottages available in September

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

7 nights from £248

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


Only a short drive to the glorious south coast and the pretty bays at Lansallos and Talland, Menabilly is tucked away in a rural setting where peace and tranquility abounds. If you...

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

7 nights from £248

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

7 nights from £260

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 £260

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

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

7 nights from £270

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 £270

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

7 nights from £282

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 £282

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

7 nights from £285

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 10 minute drive away. Soft blu...

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

7 nights from £285

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

7 nights from £285

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


Want to be at one with nature and take a break from the hustle and bustle of everyday life, then wind your way along the country lanes to the peace and beauty that abounds at Neptu...

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

7 nights from £285

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

7 nights from £295

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


Tucked away down a Cornish country lane, this contemporary barn conversion is a great base for exploring Cornwall or the perfect spot for enjoying the bountiful wildlife in the sur...

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

7 nights from £295

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

7 nights from £296 *

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


Tuell Farm is an undiscovered rural haven of peace nestling in the Tamar Valley, an Area of Outstanding Natural Beauty. There are 28 acres to explore on this tranquil farm with Gre...

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

7 nights from £296 *

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

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £297

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


A warm welcome awaits you at this gorgeous retreat for two set in the peace and tranquility of the glorious Cornish countryside. Located at the end of a pretty tree-lined private l...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £297

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

7 nights from £302

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 coas...

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

7 nights from £302

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