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 937 holiday cottages available in September

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

7 nights from £433

Gorgeous cabin sleeping 2 near Dartmouth, South Devon.


Walk the little path through the three acres of the Owners' grounds and woods and there you'll find Ashley's Shack. Up above a large lake covered in water lilies in the summer mont...

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

7 nights from £433

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £433

1 bedroom, dog friendly self catering cottage, Lifton, Dartmoor.


In an Area of Outstanding Natural Beauty, approached by a green lane, bordered by sun-dappled woodland, Leat Mill is delightful. A pretty enclosed patio overlooks tranquil surround...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £433

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

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

7 nights from £435

1 bedroom, rural cottage near the beach near Sennen, West Cornwall.


Contemporary luxury on the edge of the Cot Valley with views across open countryside to the Atlantic Ocean, sums up this gorgeous retreat. All on one level with a south-facing terr...

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

7 nights from £435

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £435

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


Located on the first floor of Shanklin Villa, a lovely Victorian property, this small studio apartment packs a punch despite its size. Enjoying beautiful sea views from its elevate...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £435

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

7 nights from £435

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


This contemporary studio apartment enjoys a great location in Shanklin. With modern decor and open plan living, it makes a cosy retreat for a couple looking for a coastal break. Wi...

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

7 nights from £435

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

7 nights from £436

1 bedroom, rural self catering cottage near Tiverton, North Devon.


This is an exceptional bolthole in a farmstead setting, shared with the friendly Owners, high up above the River Exe as it winds through the beautiful hills and woodland between Ti...

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

7 nights from £436

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

7 nights from £436

1 bedroom thatched self catering cottage near Sherborne, Dorset.


Pound Farm Cottage is a hidden gem; this listed thatched cottage has been thoughtfully renovated to create a spacious, stylish holiday home, retaining many of the original features...

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

7 nights from £436

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  • 15% off

    22 Apr 2019 - 26 Apr 2019

    £342.75 £291.34

  • 15% off

    3 May 2019 - 10 May 2019

    £442.50 £375.70

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

7 nights from £437

1 bedroom, dog friendly cottage near Mousehole, West Cornwall.


Warm and toasty, Ellas Pottery awaits you for your romantic break away enjoying the peace and plenty of this far western setting. The detached cottage is on one level with unde...

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

7 nights from £437

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

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £437

1 bedroom, coastal apartment with sea views near Kingsand, Cornwall.


With a most enviable location right on the water's edge offering breath-taking views over Plymouth Sound, the Song of the Sea is a delightful waterside apartment in the historic Fo...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £437

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

7 nights from £439

1 bedroom holiday cottage near the beach in St Just, West Cornwall.


Stunningly gorgeous, this former miner’s terraced cottage has been transformed into a beautiful retreat for couples looking for something extra special. In the cosy sitting-room a ...

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

7 nights from £439

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