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 926 holiday cottages available in September

  • Sleeps 10 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £1154

5 bedroom cottage with sea views in Mawgan Porth, North Cornwall.


Twelve Steps is just off the coast road leading down to Mawgan Porth, a real surfer’s paradise beach on the north Cornish coast. With Atlantic sea views and direct access to the be...

  • Sleeps 10 + 2 cots
  • Regret no pets
  • Changeover Fri

7 nights from £1154

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £1095.20 £876.16

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1168

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


Seacrest House is a stunning holiday home with fabulous Solent views across beautiful Appley beach and is perfect for a large family or group of friends looking for a property with...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1168

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

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1235

5 bedroom, dog friendly holiday cottage in Honiton, South Devon.


This fabulous 'grand design' barn conversion, near east Devon's famous market town of Honiton, is just a short drive inland from the breathtaking Jurassic Coast between Sidmouth an...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1235

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1287

5 bedroom, dog friendly cottage near Port Isaac, North Cornwall.


Let us introduce you to the wonderful, the classic, Pengenna Manor! Tucked away at the end of a private drive, surrounded by glorious Cornish countryside, this unique and very spec...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1287

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1348

4 bedroom, rural self catering cottage near the beach in Bembridge, Isle of Wight.


A wonderfully modern property, beautifully furnished and housed in an American-style cladded exterior, Pitt Corner is roomy, with plenty of space for the family to spread out. As w...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1348

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £1348.48 £1078.78

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1516

5 bedroom, dog friendly cottage near the beach near Lyme Regis.


Less than half a mile from the World Heritage Jurassic Coast, The Old Manor House is a beautiful 16th Century, Grade II Listed house, full of character with a delightful enclosed g...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1516

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1575

4 bedroom, rural self catering cottage near the beach in Shanklin, Isle of Wight.


Mountbatten Garden Apartment is a fabulous apartment stylishly furnished with four en suite bedrooms and comes with a private courtyard including a six person hot tub. Vibrantly de...

  • Sleeps 10 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £1575

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1600

5 bedroom, dog friendly holiday cottage near the beach in Seaview, Isle of wight.


This stunning converted coach house, benefitting from a fabulous location within the grounds of the Priory Estate, is an exceptional holiday home-from-home. The Priory Coach House ...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1600

View
  • 20% off

    29 Mar 2019 - 5 Apr 2019

    £1199.80 £959.84

We’ve been raising the standards of self catering holidays since 1977.

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Thu

7 nights from £1613

5 bedroom, dog friendly cottage with sea views near Port Isaac.


Wow, Upton Mill is stunning! Perched on the north Cornish coast just minutes from dog-friendly Trebarwith Strand and within easy reach of Port Isaac and Padstow, this is a perf...

  • Sleeps 10 + cot
  • Dogs welcome
  • Changeover Thu

7 nights from £1613

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1711

5 bedroom self catering cottage near the beach in Cowes, Isle of Wight


A truly amazing, contemporary home with views directly out to sea, in the popular sailing town of Cowes. Offering exceptional quality throughout the whole home this is a superb bas...

  • Sleeps 10 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1711

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