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 1159 holiday cottages available in September

The Barn at Little Windsor is a 1 bedroom, dog friendly holiday cottage near Looe, South Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £471

The Barn at Little Windsor

5968

1 bedroom, dog friendly holiday cottage near Looe, South Cornwall.


Nestled in the exceptionally pretty Looe valley, with wonderful views across the rolling countryside, come and immerse yourself in Cornish charm, rural bliss and a wonderful wildli...

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

7 nights from £471

Bluebell is a Dog-friendly showmans wagon with outdoor bath near Mawgan Porth, North Cornwall
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £641

Bluebell

5988

Dog-friendly showmans wagon with outdoor bath near Mawgan Porth, North Cornwall


We're super excited to introduce you to our very first showman's wagon, a stunningly romantic hideaway for two nestled in north Cornwall that's dog friendly too. Lovingly handcr...

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

7 nights from £641

We’re here to help you find your perfect place to stay 7 days a week.

Quay Cottage is a 2 bedroom, dog friendly cottage with sea views in Devoran, Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £741

Quay Cottage

5975

2 bedroom, dog friendly cottage with sea views in Devoran, Cornwall.


With creekside views where you can watch the tide ebb and flow this cottage is the perfect escape. Tucked away in the heart of the charming creekside village of Devoran, this beaut...

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

7 nights from £741

Island Cottage is a 3 bedroom, dog friendly cottage set on the beach in Kingsand, Cornwall.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1080

Island Cottage

5960

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


Set right on the beach in the charming village of Kingsand, treat yourself to the ultimate seaside escape where the sound of the waves lapping on the seashore become your daily sou...

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

7 nights from £1080

The Milk Shed is a 2 bedroom, dog friendly holiday cottage near Padstow, North Cornwall.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £651

The Milk Shed

5977

2 bedroom, dog friendly holiday cottage near Padstow, North Cornwall.


Looking for a retreat that offers peace and tranquility in abundance, yet perfect for immersing yourself in north coast living - then look no further than The Milk Shed. Nestled in...

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

7 nights from £651

Water's Edge is a 2 bedroom, dog friendly apartment with sea views in Looe, Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £736

Water's Edge

5980

2 bedroom, dog friendly apartment with sea views in Looe, Cornwall.


With stunning estuary views over the waters of the Looe River to the countryside beyond and stylish interiors - Water's Edge is an absolute gem! Boasting a prime location, high abo...

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

7 nights from £736

Ferry Point House is a 3 bedroom self catering cottage with sea views near Helensburgh.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £3000

Ferry Point House

5972

3 bedroom self catering cottage with sea views near Helensburgh.


What a fantastic view! Escape to this hidden gem in Scotland and delight in the open vistas across the loch and mountains beyond which will captivate your imagination. This con...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £3000

The Works is a 2 bedroom, dog friendly cottage near the beach in Penzance, Cornwall.
  • Sleeps 4
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £534 *

The Works

5970

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


Tucked away on a quiet road in the centre of vibrant Penzance, The Works is a unique reverse-level house which offers a stylish and welcoming base to explore the beauty and culture...

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

7 nights from £534 *

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

Ocean Break is a 2 bedroom holiday cottage near the beach in Croyde, North Devon.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £444 *

Ocean Break

5965

2 bedroom holiday cottage near the beach in Croyde, North Devon.


Pack your bags and head to the glorious golden sands of Croyde beach with a stay at Ocean Break. This glorious north Devon seaside village is cradled by the surrounding hills. Afte...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £444 *

Alma is a Shepherd's Hut with hot tub near South Molton.
  • Sleeps 2
  • No pets
  • Changeover Fri

From £132 per night

Alma

5844

Shepherd's Hut with hot tub near South Molton.


If you go down to the woods today, you'll discover this Devonshire beauty - a stunning, romantic hideaway for those seeking the wilder things in life… Welcome to Alma, our bijou...

  • Sleeps 2
  • No pets
  • Changeover Fri

From £132 per night

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.