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 960 holiday cottages available in September

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

7 nights from £512

2 bedroom, dog friendly holiday cottage in Portreath, North Cornwall.


Chy Lowen is a perfect combination of traditional Cornish cottage charm, contemporary comfort and stylish living with a welcoming and relaxing feel throughout – a real home-from-ho...

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

7 nights from £512

  • Sleeps 4
  • Regret no pets
  • Changeover Sat

7 nights from £512

2 bedroom cottage near Kingsbridge, south Devon.


Found in the quiet hamlet of Leigh, Grade I Listed Leigh Barton is partly a designated ancient monument and a fine example of a medieval monastic grange and outbuildings, where the...

  • Sleeps 4
  • Regret no pets
  • Changeover Sat

7 nights from £512

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  • 20% off

    23 Mar 2019 - 30 Mar 2019

    £491.62 £393.30

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

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

7 nights from £514

2 bedroom self catering cottage near the beach in Ryde, Isle of Wight.


Venice Lodge is a Georgian cottage located in a quiet residential area of the popular seaside town of Ryde. This is a unique house that you will not soon forget. If you long for th...

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

7 nights from £514

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £514.20 £411.36

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

7 nights from £515

2 bedroom, dog friendly cottage near the beach in Sennen with a pool.


Immaculate and furnished to a very high standard, this first (or last) contemporary retreat has a wood-burner, use of the large outdoor heated swimming pool (available from the beg...

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

7 nights from £515

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

7 nights from £515

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


Lena is just beautiful with a cosy sitting/dining-room, a wood-burner and under-floor heating which keeps the slate floors downstairs warm underfoot. A modern well-equipped kitchen...

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

7 nights from £515

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

7 nights from £518

2 bedroom holiday cottage near the beach in Coverack, West Cornwall.


One of the oldest cottages in the picturesque seaside village of Coverack, Jubilee Cottage has been beautifully and sensitively updated to the highest standard but still retains mu...

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

7 nights from £518

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

7 nights from £520 *

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


Stunning can be an over-used term but Ida Cottage really lives up to the description. Under-floor heating throughout, toasty slate-flooring downstairs and oak-flooring upstairs, th...

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

7 nights from £520 *

  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £522

2 bedroom, dog friendly holiday cottage near Dulverton, Somerset.


Withypool is at the heart of the beautiful Exmoor National Park and Riverview has a wonderful elevated village position with panoramic views of the River Barle below and the open m...

  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £522

We’re here to help you find your perfect place to stay 7 days a week.

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

7 nights from £524 *

3 bedroom, dog friendly holiday cottage in Somerset, near Honiton.


This luxury farmhouse in the Blackdown Hills, with wonderful garden hot tub, is in an idyllic rural setting on the edge of the village of Bishopswood, within walking distance of th...

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

7 nights from £524 *

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

7 nights from £526

2 bedroom, rural self catering cottage near Helston, West Cornwall.


The Cow Shed is a thoughtful conversion of a lovely old stone farm building that for generations was home to the farm's herd of dairy cows and calves. Farmed by the same family for...

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

7 nights from £526

View
  • 20% off

    30 Mar 2019 - 6 Apr 2019

    £501.80 £401.44

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