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. 

Isle of Wight Ferry Booking Our exclusive ferry discounts will make your island trip with Classic plain sailing.

We have 1037 holiday cottages available in September

Meadowcliff is a 8 bedroom, dog friendly home with hot tubs and sea views in Shaldon, South Devon.
  • Sleeps 18 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £4148

Meadowcliff

4096

8 bedroom, dog friendly home with hot tubs and sea views in Shaldon, South Devon.


**Meadowcliff is even bigger and better. Now equipped to accommodate 18 guests, offering a second larger hot tub in addition to the existing tub, and boasting an adventure slide to...

  • Sleeps 18 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £4148

Sunsets (over Rinsey) is a 1 bedroom, dog friendly cottage with sea views in Praa Sands.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £591

Sunsets (over Rinsey)

4077

1 bedroom, dog friendly cottage with sea views in Praa Sands.


There really are fabulous sunsets (and sea views) over Rinsey and you will be well placed to see them at this gorgeous contemporary annexe to the owners' home. Cross the thresh...

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

7 nights from £591

East Barn is a 1 bedroom thatched, dog friendly cottage near Porthleven, Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £394

East Barn

4092

1 bedroom thatched, dog friendly cottage near Porthleven, Cornwall.


Tucked away in the hamlet of Crowan, East Barn is a delightful thatched barn conversion. The owners have beautifully converted the barn, keeping the classic features with high ceil...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £394

West Barn is a 1 bedroom thatched, dog friendly cottage near Porthleven, Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £385

West Barn

4093

1 bedroom thatched, dog friendly cottage near Porthleven, Cornwall.


One of a pair of detached barn conversions tucked away in the tranquil hamlet of Crowan, as soon as you pull into the drive, you feel as though you have stepped in to a story book....

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £385

Little Meadowside is a 1 bedroom self catering cottage in Wadebridge, North Cornwall.
  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £419

Little Meadowside

4088

1 bedroom self catering cottage in Wadebridge, North Cornwall.


Little Meadowside is a delightful little bolthole for two, located on the edge of the vibrant town of Wadebridge. Nestled in a tiny hamlet, down a private lane, you truly are tucke...

  • Sleeps 2
  • No pets
  • Changeover Sat

7 nights from £419

Miranda Cottage is a 3 bedroom, dog friendly holiday cottage near Helford, West Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £903

Miranda Cottage

4046

3 bedroom, dog friendly holiday cottage near Helford, West Cornwall.


Miranda Cottage is a quintessential Cornish thatched cottage in the heart of the village of St Martin, a short distance from the famous sailing waters of the Helford River. Bea...

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

7 nights from £903

Our guests rate us 4.8/5 on Feefo, the independent review site.

Lakeview House is a 4 bedroom, rural self catering cottage with a hot tub near Honiton, South Devon.
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £709 *

Lakeview House

4074

4 bedroom, rural self catering cottage with a hot tub near Honiton, South Devon.


Lakeview House is a stunning holiday property in east Devon, inland from the World Heritage Jurassic Coast from Budleigh Salterton and Sidmouth in east Devon through to Lyme Regis ...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £709 *

Lakeside House is a 4 bedroom, rural self catering cottage with a hot tub near Honiton, South Devon.
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £709 *

Lakeside House

4075

4 bedroom, rural self catering cottage with a hot tub near Honiton, South Devon.


This stunning family-sized holiday home with private hot tub, large enclosed garden and wonderful stocked fishing lake is in east Devon, a short and easy drive from the World Herit...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £709 *

61 Solent View is a 4 bedroom, dog friendly holiday cottage, with sea views in Seaview, Isle of Wight
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1039 *

61 Solent View

4078

4 bedroom, dog friendly holiday cottage, with sea views in Seaview, Isle of Wight


On the outskirts of Seaview and within a few minutes' walk from Seagrove Bay, take in the stunning sea views from not one but two balconies. 61 Solent View is a wonderful holiday h...

  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1039 *

Keepers Cottage is a 4 bedroom, rural self-catering cottage on the outskirts of Wootton, Isle of Wight
  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £926

Keepers Cottage

4070

4 bedroom, rural self-catering cottage on the outskirts of Wootton, Isle of Wight


This gorgeous stone cottage is tucked away in the most idyllic and tranquil location; surrounded by fields and woodland, this is the perfect holiday setting to truly escape from it...

  • Sleeps 7 + cot
  • No pets
  • Changeover Fri

7 nights from £926

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