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 927 holiday cottages available in September

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

7 nights from £371

1 bedroom self catering cottage in Helston, West Cornwall.


Tucked away and hidden from view yet only a short walk from Helston with its shops, pubs and cafes, this delightful cottage is beautifully furnished and equipped to a very high sta...

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

7 nights from £371

View
  • 20% off

    30 Mar 2019 - 6 Apr 2019

    £344.50 £275.60

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

7 nights from £371 *

2 bedroom holiday cottage near Ilminster, Somerset.


Flax Barn is located in the beautiful south Somerset village of Barrington, not far from the Dorset border. Barrington Court - one of several National Trust properties in the immed...

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

7 nights from £371 *

View
  • 20% off

    5 Apr 2019 - 12 Apr 2019

    £474.30 £379.44

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

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

7 nights from £372

1 bedroom, dog friendly holiday cottage near Fowey.


Meadowsweet is the slightly larger of the two barns. Two steps lead up into the living-room, with its polished wood floors and comfortable furnishings. The kitchen-area is fitted i...

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

7 nights from £372

View
  • 20% off

    22 Mar 2019 - 29 Mar 2019

    £319.58 £255.66

  • 20% off

    5 Apr 2019 - 12 Apr 2019

    £344.38 £275.50

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

7 nights from £372

1 bedroom, dog friendly holiday cottage near Fowey.


Cowslip, like Meadowsweet (1430), has two steps leading into the living-room, where neutral walls and polished wood floors frame the warmly coloured furnishings. There is a pine fi...

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

7 nights from £372

View
  • 20% off

    22 Mar 2019 - 29 Mar 2019

    £319.58 £255.66

  • 20% off

    5 Apr 2019 - 12 Apr 2019

    £344.38 £275.50

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £372

1 bedroom, rural holiday cottage near Helston, West Cornwall.


At the end of a private lane and set within a peaceful courtyard flanked by a small group of other converted barns, The Croft is a pretty little self-contained annexe to the Owner’...

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £372

View
  • 30% off

    6 Apr 2019 - 13 Apr 2019

    £404.86 £283.50

  • 25% off

    13 Apr 2019 - 20 Apr 2019

    £404.86 £303.75

  • 25% off

    20 Apr 2019 - 27 Apr 2019

    £390.20 £292.50

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

7 nights from £372

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


Butterwell Cottage is a lovely little hideaway for couples just a couple of miles inland from the coastal footpaths that wend their way along Whitsand, Lantivet and Looe bays. ...

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

7 nights from £372

View
  • 20% off

    22 Mar 2019 - 29 Mar 2019

    £346.09 £276.87

  • 20% off

    5 Apr 2019 - 12 Apr 2019

    £404.86 £323.89

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

7 nights from £372

1 bedroom, dog friendly cottage near the beach in St Agnes, Cornwall.


Beacon Top Bottom is a charming little cottage nestled in the slopes of St Agnes Beacon. Ideally situated for exploring this stunning area of north Cornwall, this cosy little bolth...

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

7 nights from £372

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £373

1 bedroom thatched, dog friendly cottage near Helston, West Cornwall.


West Barn is one of a pair of detached, thatched barn conversions tucked away in the hamlet of Crowan. This traditional barn has been sympathetically converted into a lovely holida...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £373

View
  • 10% off

    5 Apr 2019 - 12 Apr 2019

    £406.10 £365.40

  • 10% off

    12 Apr 2019 - 19 Apr 2019

    £406.10 £365.40

  • 10% off

    19 Apr 2019 - 26 Apr 2019

    £391.39 £351.90

  • 10% off

    26 Apr 2019 - 3 May 2019

    £359.61 £324.00

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £375

1 bedroom, rural apartment near the beach in Seaton, South Devon.


High above the Axe estuary, this hidden retreat is just a short walk from the South West Coast Path along the stunning east Devon and west Dorset Jurassic Coast. Steps lead down...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £375

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £376

1 bedroom self catering apartment near Ventnor, Isle of Wight


Sea Song is an attractive one bedroom, first floor apartment overlooking beautiful communal gardens and surrounded by woodland on the southernmost tip of the island. Perfect for ro...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £376

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