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

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 964 holiday cottages available in September

Freshfields is a 4 bedroom secluded cottage with large grounds near Dorchester, Dorset.
  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £1101

Freshfields

5706

4 bedroom secluded cottage with large grounds near Dorchester, Dorset.


Freshfields is a truly outstanding property in a picturesque Dorset village. Recently renovated throughout, the house provides space and privacy for all the family. Just a short dr...

  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £1101

Aurora at 24 Acres is a Shepherds Hut in Devon with outdoor bath and luxury interiors.
  • Sleeps 2
  • No pets
  • Changeover Fri

From £134 per night

Aurora at 24 Acres

5736

Shepherds Hut in Devon with outdoor bath and luxury interiors.


Welcome to Aurora, a gorgeous shepherd's hut for two, hidden away in a secluded setting in the Blackdown Hills. Nestled within a peaceful meadow on a 24-acre site and surrounded by...

  • Sleeps 2
  • No pets
  • Changeover Fri

From £134 per night

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

7 nights from £1800

Penfoye

5728

3 bedroom, dog friendly cottage with sea views near Fowey, Cornwall.


If there was a definition of 'heaven on earth' then Penfoye would be it. With spellbinding waterside scenes, beautifully curated interiors and glorious gardens, this extra-special ...

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

7 nights from £1800

Bentinck is a 3 bedroom self catering cottage near the beach in Ventnor.
  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £792

Bentinck

5724

3 bedroom self catering cottage near the beach in Ventnor.


Located in a quiet spot, just moments from the vibrant high street and picturesque seafront, Bentinck offers a welcoming, beautifully refurbished home with everything you could wis...

  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £792

Rivendell Cottage is a 2 bedroom, dog friendly cottage near Camelford, North Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £473

Rivendell Cottage

5732

2 bedroom, dog friendly cottage near Camelford, North Cornwall.


Wind your way along the country lanes to this picture-perfect cottage, nestled in the rural hamlet of Tremail in the heart of north Cornwall. Serving up the best of both worlds, th...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £473

Briar Lea is a 2 bedroom, dog friendly cottage with sea views in Robin Hoods Bay.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £744

Briar Lea

5694

2 bedroom, dog friendly cottage with sea views in Robin Hoods Bay.


Nestled in the quiet coastal village of Fylingthorpe with views across the sea to the rugged Yorkshire coastline and within minutes of the historic Robin Hood's Bay, this beautiful...

  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £744

The Hayloft is a 2 bedroom thatched, dog friendly cottage near Okehampton, Devon.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £650

The Hayloft

5734

2 bedroom thatched, dog friendly cottage near Okehampton, Devon.


Escape to rural Devon bliss and become an Exbourne village local for a week; from walking the numerous bridle paths to popping to the local pub for a swift half, not forgetting you...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £650

View
  • 20% off

    9 Aug 2024 - 16 Aug 2024

    £855.00 £684.00

  • 20% off

    23 Aug 2024 - 30 Aug 2024

    From £855.00 £684.00

The Threshing Barn is a 3 bedroom, dog friendly holiday cottage near Okehampton, North Devon.
  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £600 *

The Threshing Barn

5733

3 bedroom, dog friendly holiday cottage near Okehampton, North Devon.


Nestled in a quaint west Devon village, escape to the tranquility of village life and a slower pace at The Threshing Barn. This newly fully refurbished barn offers style and charm ...

  • Sleeps 7 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £600 *

View
  • 20% off

    16 Aug 2024 - 23 Aug 2024

    From £956.00 £956.00

  • 20% off

    23 Aug 2024 - 30 Aug 2024

    From £956.00 £956.00

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

Ty Coedwig Treehouse is a Luxury treehouse with outdoor bathtub in Powys, Wales.
  • Sleeps 2 + 2 cots
  • No pets
  • Changeover Fri

From £170 per night

Ty Coedwig Treehouse

5729

Luxury treehouse with outdoor bathtub in Powys, Wales.


Embrace nature with a stay in this most magical setting, a beautiful handcrafted treehouse complete with an al fresco bathtub, set in tranquil woodland and surrounded by nature, de...

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

From £170 per night

Mera Ghar is a 5 bedroom, dog friendly holiday cottage near Plymouth, South Devon.
  • Sleeps 10 + 3 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1325

Mera Ghar

5713

5 bedroom, dog friendly holiday cottage near Plymouth, South Devon.


Escape to a south west holiday abode of dreams, on the outskirts of the maritime city of Plymouth, with the beauty of Dartmoor on your doorstep. From style to fun, no detail has be...

  • Sleeps 10 + 3 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1325

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