Holiday Cottages for September

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

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

We have 1403 holiday cottages available in September

Y Beudy is a 4 bedroom, dog friendly cottage with sea views near St Davids.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £800

Y Beudy

6107

4 bedroom, dog friendly cottage with sea views near St Davids.


With far reaching, uninterrupted, spectacular sea views, set in eight acres of countryside and expansive lawns, gorgeous, stone-built Y Beudy is a charming conversion of a traditio...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £800

Ysgubor is a 2 bedroom, dog friendly cottage with sea views near St Davids.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £600

Ysgubor

6106

2 bedroom, dog friendly cottage with sea views near St Davids.


Nestling in the magnificent glory of the dramatic, rugged Pembrokeshire coastline, offering golden beaches, crystal blue sea and pretty seaside villages, dog-friendly, Ysgubor (Gra...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £600

Mount Folly Farmhouse is a 3 bedroom, dog friendly cottage with sea views near Kingsbridge.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1326

Mount Folly Farmhouse

6108

3 bedroom, dog friendly cottage with sea views near Kingsbridge.


Welcoming you to Mount Folly Farmhouse, a fabulous retreat which enjoys both coast and country. On entering Mount Folly Farmhouse you will feel immediately at home, this spacious y...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1326

Mount Folly Penthouse is a 3 bedroom apartment with sea views near Kingsbridge, South Devon.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1326

Mount Folly Penthouse

6109

3 bedroom apartment with sea views near Kingsbridge, South Devon.


If you're looking for a beautifully finished penthouse apartment, boasting the most spectacular views from almost every window, a glorious hot tub and outdoor sauna perched overloo...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1326

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Boathyde Estate

  • Sleeps 16 + 4 cots in 2 properties
  • Changeover Fri

7 nights from £4014

Boathyde is a 5 bedroom, dog friendly cottage with sea views in Appledore, Devon.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £2919 *

Boathyde

6095

5 bedroom, dog friendly cottage with sea views in Appledore, Devon.


Tucked away at the end of a quiet lane and hidden behind electric gates, this exceptional north Devon retreat will make a lasting first impression. From the moment you arrive, you'...

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

7 nights from £2919 *

The Moorings is a 4 bedroom, dog friendly cottage with sea views in Appledore, Devon.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1094 *

The Moorings

6096

4 bedroom, dog friendly cottage with sea views in Appledore, Devon.


Tucked away behind electric gates in a prime spot in beautiful north Devon, you'll find this stylish holiday home offering the kind of setting that makes you relax the moment you a...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1094 *

Duxbury Lodge is a Dog-friendly elegant countryside lodge for two
  • Sleeps 2
  • Dogs welcome

Duxbury Lodge

201

Dog-friendly elegant countryside lodge for two


Duxbury Lodge is a contemporary barn conversion set alongside Duxbury Cottage, offering a stylish rural retreat for two in the south of the island. Thoughtfully designed and beauti...

  • Sleeps 2
  • Dogs welcome
Dunks Cottage is a 4 bedroom, dog friendly self catering cottage near Cranbrook.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1266

Dunks Cottage

6074

4 bedroom, dog friendly self catering cottage near Cranbrook.


Overlooking the village green of Sandhurst, Kent, in the beautiful High Weald National Landscape (Area of Outstanding Natural Beauty), this wonderfully spacious, semi-detached cott...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1266

The Old Stables is a 2 bedroom self catering cottage near Bridlington.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £808

The Old Stables

6093

2 bedroom self catering cottage near Bridlington.


Welcome to the Old Stables, a sanctuary of weathered red brick and rustic charm that captures the very soul of the Yorkshire Wolds. If you are looking for a getaway that swaps the ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £808

Load 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.