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 1396 holiday cottages available in September

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

Little Chywoon Barn is a 2 bedroom cottage near Perranporth, North Cornwall
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £528 *

Little Chywoon Barn

6104

2 bedroom cottage near Perranporth, North Cornwall


Tucked away in peaceful countryside, this retreat is surrounded by verdant rural views and peaceful birdsong but is only 10 minutes from the golden sands of Perranporth. This charm...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £528 *

North Wing is a 2 bedroom apartment with sea views near Marazion, West Cornwall.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £780 *

North Wing

6113

2 bedroom apartment with sea views near Marazion, West Cornwall.


Perched proudly above Mount's Bay, North Wing apartment forms part of the historic Acton Castle, an iconic landmark built in 1775 and listed with Historic England. Constructed from...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £780 *

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The Ballacloan is a Ground floor apartment conveniently located on the promenade in Douglas
  • Sleeps 4 + cot
  • No pets

The Ballacloan

193

Ground floor apartment conveniently located on the promenade in Douglas


A coastal haven in the heart of Douglas Promenade The Ballacloan is the perfect family apartment to enjoy the heart of the Isle of Man in all its glory. Set directly on the prom...

  • Sleeps 4 + cot
  • No pets
9 West View is a 3 bedroom self catering cottage near the beach in Beer, South Devon.
  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £766

9 West View

6081

3 bedroom self catering cottage near the beach in Beer, South Devon.


Welcome to 9 West View, a delightful and characterful cottage nestled perfectly on the Jurassic Coast. This charming, characterful, terraced cottage offers a great base for friends...

  • Sleeps 5 + cot
  • No pets
  • Changeover Fri

7 nights from £766

The Clypse is a Seaside first floor apartment on Douglas Promenade
  • Sleeps 4 + cot
  • No pets

The Clypse

194

Seaside first floor apartment on Douglas Promenade


A front-row coastal retreat with timeless bay views Welcome to The Clypse, an island retreat nestled on the beautiful Douglas Promenade, just steps away from sandy shores and so...

  • Sleeps 4 + cot
  • No pets
Sea Salt is a Refined boutique stay near Castletown’s harbour & history
  • Sleeps 4 + cot
  • No pets

Sea Salt

199

Refined boutique stay near Castletown’s harbour & history


Sea Salt is a beautifully refurbished hideaway on historic Queen Street, offering an indulgent blend of contemporary luxury and homely warmth in the heart of Castletown. Thoughtful...

  • Sleeps 4 + cot
  • No pets
Mewstone View is a 4 bedroom, dog friendly cottage near the beach in Kingsand, Cornwall.
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1326 *

Mewstone View

6088

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


Gather family and friends, and your four-legged companions, and settle into holiday life at the stylish Mewstone View. Tucked into the peaceful countryside of Cornwall's "Forgotten...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1326 *

Larch Cottage is a 2 bedroom, dog friendly cottage near the beach in Kingsand, Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £740

Larch Cottage

6090

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


Come and enjoy a well deserved break at this contemporary retreat, which serves up the perfect blend of countryside calm and coastal charm. Set in the rolling fields of Cornwall's ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £740

Need more time? Reserve any cottage for up to 24 hours before booking.

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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.