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 1036 holiday cottages available in September

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £431

Gorgeous Shepherds Hut sleeping two near St Ives, West Cornwall.


Found in a tranquil and unspoilt part of far west Cornwall, approached by lanes full of wildflowers in the spring and summer, this gorgeous hideaway is set in its own sheltered and...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £431

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £431

1 bedroom, dog friendly shepherds hut with wood-fired hot tub near Exeter.


This beautifully presented shepherd's hut is as much a part of the landscape here as the ancient oak which gives it its name. The two stand side-by-side at the top of a gently slop...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £431

We are Gold accredited with the Green Tourism Business Scheme.

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

7 nights from £431

Gorgeous shepherds hut sleeping 2 near Lyme Regis, South Devon.


The location high above the Axe Valley as it heads to the Jurassic Coast just a few miles away could not be more magical. Easy to reach, yet off the beaten track for the last adven...

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

7 nights from £431

View
  • 20% off

    21 Dec 2018 - 28 Dec 2018

    £562.50 £449.60

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £431

1 bedroom, dog friendly shepherds hut with own fishing lake near Exeter.


A few miles outside the Roman city of Exeter, a few miles inland from the east Devon Jurassic Coast, and many miles away from the fast pace of everyday life, sits a delightful shep...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £431

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

7 nights from £431

1 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.


This delightful traditional stone cottage is a tranquil village bolthole near Glastonbury, just south of Somerset's stunning Mendip Hills, with their spectacular landscapes and dra...

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

7 nights from £431

View
  • 15% off

    14 Dec 2018 - 21 Dec 2018

    £627.48 £532.95

  • 20% off

    21 Dec 2018 - 28 Dec 2018

    £627.48 £501.60

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

7 nights from £431

1 bedroom holiday cottage with sea views near Dawlish, South Devon.


This delightful and spacious detached cottage provides the perfect getaway location for two. Furnished and equipped to a very high standard, The Apple House offers you a wonderful ...

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

7 nights from £431

  • 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

View
  • 20% off

    28 Dec 2018 - 4 Jan 2019

    £566.10 £452.80

  • 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

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

  • 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

View
  • 20% off

    21 Dec 2018 - 28 Dec 2018

    £434.99 £348.00

  • 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

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