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 1177 holiday cottages available in September

Isla Rose is a Dog friendly shepherds hut near Pulborough.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

From £92 per night

Isla Rose

5948

Dog friendly shepherds hut near Pulborough.


This oh-so-romantic shepherd's hut for two lies in the beautiful countryside of West Sussex and offers an idyllic, peaceful escape that's dog friendly too. Just a mere two hours...

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

From £92 per night

Sunset Skies is a 2 bedroom self catering apartment with sea views in Hunstanton.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £698

Sunset Skies

5865

2 bedroom self catering apartment with sea views in Hunstanton.


Welcome to Sunset Skies - a stylish, first floor apartment located in the seaside town of Hunstanton, aptly named due to the way the sky lights up at dusk, bursting into bold, vibr...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £698

Maple Cottage is a 1 bedroom, dog friendly self catering cottage near Milnthorpe.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £600

Maple Cottage

5874

1 bedroom, dog friendly self catering cottage near Milnthorpe.


Welcome to Maple Cottage, with its upside down construction and large windows which give you the feeling of sitting among the trees. Perched on the edge of the South Lakes and with...

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

7 nights from £600

Low Rigg is a 3 bedroom, dog friendly self catering cottage near Hawes.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £838

Low Rigg

5770

3 bedroom, dog friendly self catering cottage near Hawes.


Come and enjoy a break in the Yorkshire Dales and relax with the rustic charm of an original Yorkshire stone cottage. Semi-detached Low Rigg is huddled at the edge the charming vil...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £838

Millook is a 2 bedroom lodge with sea views near Bude, North Cornwall.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £812

Millook

5937

2 bedroom lodge with sea views near Bude, North Cornwall.


Escape to north Devon and delight in a view that will captivate your imagination, giving you the freedom to breathe and relax into you holiday! This striking lodge not only boasts ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £812

Trebarwith is a 3 bedroom, dog friendly lodge with sea views near Bude, Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1050

Trebarwith

5879

3 bedroom, dog friendly lodge with sea views near Bude, Cornwall.


With breathtaking views across Bude and the gorgeous north Devon coastline, thanks to the floor to ceiling windows, this unique and beautifully crafted, dog-friendly luxury lodge s...

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

7 nights from £1050

Northcott is a 3 bedroom lodge with sea views near Bude, North Cornwall.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £1050

Northcott

5938

3 bedroom lodge with sea views near Bude, North Cornwall.


With a bird's eye view of the rugged and beautiful north Devon coastline, not only have you discovered the perfect retreat to recharge and unwind, you've found an enviable location...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £1050

7 Chapel Street is a 2 bedroom, dog friendly cottage near the beach in Mousehole.
  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £550 *

7 Chapel Street

5872

2 bedroom, dog friendly cottage near the beach in Mousehole.


Tucked away in the heart of the historic fishing village of Mousehole, 7 Chapel Street is a sweet two bedroom cottage offering a perfect coastal escape. Brimming with charm, the co...

  • Sleeps 3 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £550 *

Be in the know… Sign up to our newsletter for holiday inspiration, offers and all things Classic.

2 Old Turnpike Cottages is a 2 bedroom, dog friendly self catering cottage with hot tub near Chipping Norton.
  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £1020

2 Old Turnpike Cottages

5866

2 bedroom, dog friendly self catering cottage with hot tub near Chipping Norton.


Tucked away in the picturesque village of Middle Barton, just a short drive from Chipping Norton and the exclusive Soho Farmhouse lies this quintessential, dog-friendly Cotswold Co...

  • Sleeps 4
  • Dogs welcome
  • Changeover Fri

7 nights from £1020

27 Marine Parade is a 3 bedroom holiday cottage with sea views in St Mawes, South Cornwall.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £945

27 Marine Parade

5856

3 bedroom holiday cottage with sea views in St Mawes, South Cornwall.


Perfectly positioned in St Mawes overlooking the clear blue sea towards St Anthony Head and beyond, 27 Marine Parade is a stone’s throw away from the pretty harbour and gorgeous be...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £945

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.