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 1375 holiday cottages available in September

The Sandy Den is a 1 bedroom, dog friendly apartment with sea views in Shaldon, Devon.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £649

The Sandy Den

6156

1 bedroom, dog friendly apartment with sea views in Shaldon, Devon.


Introducing The Sandy Den, a fabulous ground floor retreat for two within a converted Victorian residence located in the heart of the village of Shaldon in Teignmouth. This fabulou...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £649

Hollyhocks is a 3 bedroom, dog friendly cottage near the beach in Kingsand, Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1176

Hollyhocks

6152

3 bedroom, dog friendly cottage near the beach in Kingsand, Cornwall.


Wind your way along the quiet country lanes to this charming rural retreat, tucked away in Cornwall's breathtakingly beautiful "forgotten corner". Boasting wonderful views of the s...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1176

Wringford Cottages

  • Sleeps 26 + 7 cots in 4 properties
  • Changeover Sat

7 nights from £5414

Coniston is a
  • Sleeps 4
  • No pets

Coniston

213


Nestled on sought-after Scarlett Road in Castletown, this beautifully presented bungalow enjoys stunning sea views and offers a peaceful coastal retreat ideal for those seeking com...

  • Sleeps 4
  • No pets
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Best company for UK holiday home rentals

Calf View is a Tranquil Cregneash cottage overlooking the Calf of Man
  • Sleeps 5 + cot
  • Dogs welcome

Calf View

206

Tranquil Cregneash cottage overlooking the Calf of Man


Perched above the timeless village of Cregneash, Calf View is a serene cottage with views framed by sweeping Manx vistas stretching towards shimmering seas and the wild beauty of t...

  • Sleeps 5 + cot
  • Dogs welcome
Bramley Lodge is a 1 bedroom self catering cottage near Heathfield.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £85 per night

Bramley Lodge

6137

1 bedroom self catering cottage near Heathfield.


Soak up the scenic views of this enchanting lodge that sits within an orchard in the High Weald National Landscape. Its peaceful location is the perfect escape for a romantic getaw...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £85 per night

Fenella Cottage is a Stylish coastal cottage in Peel, moments from the sandy beach
  • Sleeps 5 + 2 cots
  • No pets

Fenella Cottage

212

Stylish coastal cottage in Peel, moments from the sandy beach


This beautifully finished coastal cottage in the heart of Peel offers an effortless blend of contemporary comfort and genuine homely charm, just moments from the town's historic ha...

  • Sleeps 5 + 2 cots
  • No pets
The Beach House is a 3 bedroom, dog friendly cottage with sea views near St Davids.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £767 *

The Beach House

6164

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


With a winning combination of contemporary comforts, character-filled living spaces, exposed beams and many other original features, just yards from the rolling surf at Abereiddy b...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £767 *

Bay Cottage is a 2 bedroom self catering cottage near the beach in Cowes.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £637

Bay Cottage

6150

2 bedroom self catering cottage near the beach in Cowes.


Tucked away in the charming village of Gurnard on the northwest coast of the Isle of Wight, this cosy two bedroom cottage offers a relaxed coastal lifestyle, complete with a pretty...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £637

Cuckoo Cottage is a 2 bedroom, dog friendly cottage near the beach in St Agnes, Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £756

Cuckoo Cottage

6141

2 bedroom, dog friendly cottage near the beach in St Agnes, Cornwall.


This bijou bolthole has luxurious interiors and is set in a fabulous location in the heart of St Agnes. Cuckoo Cottage is a charming, terraced cottage which has been thoughtfully c...

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

7 nights from £756

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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.