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 743 holiday cottages available in September

Harmon Vale is a 5 bedroom, dog friendly holiday cottage with sea views in Solva.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1456 *

Harmon Vale

6015

5 bedroom, dog friendly holiday cottage with sea views in Solva.


Seaside serenity, spacious comfort, breathtaking sea views, and a blissful spa tub, that’s Harmon Vale. This stunning holiday home is the perfect destination for families, friends ...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1456 *

St Harmon  is a 5 bedroom, dog friendly holiday cottage with sea views in Solva.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1456 *

St Harmon

6016

5 bedroom, dog friendly holiday cottage with sea views in Solva.


Enjoy a blissful coastal break in St Harmon, a superb three-storey property with luxurious hot tub, located in one of the prettiest harbour villages in Wales, in Upper Solva, nestl...

  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1456 *

Blackberry Cottage is a 4 bedroom, dog friendly holiday cottage near the beach in Heacham.
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1080 *

Blackberry Cottage

5983

4 bedroom, dog friendly holiday cottage near the beach in Heacham.


Nestled within a row of quaint cottages and close to the sandy dunes and beaches of South Beach, this gorgeous dog-friendly retreat can be enjoyed year-round with loved ones as wel...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1080 *

The Granary is a 2 bedroom self catering cottage near Moretonhampstead, South Devon.
  • Sleeps 4 + cot
  • No pets
  • Changeover Thu

7 nights from £999

The Granary

6010

2 bedroom self catering cottage near Moretonhampstead, South Devon.


If it's a superb rural retreat you are looking for, look no further, The Granary at Greenawell Farm is the perfect package. The Granary is a beautiful stone cottage, finished to an...

  • Sleeps 4 + cot
  • No pets
  • Changeover Thu

7 nights from £999

Greenawell Farm Cottages

  • Sleeps 9 + 4 cots in 3 properties
  • Changeover Fri

7 nights from £2025

Carter's Cottage is a 1 bedroom self catering cottage near Hailsham.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £491

Carter's Cottage

6005

1 bedroom self catering cottage near Hailsham.


This cosy and well-appointed semi-detached country retreat sits on a working heavy horse farm, perfect for couples or solo travellers looking to unwind, reconnect and enjoy the slo...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £491

Port and Starboard
 is a 4 bedroom holiday cottage with sea views in St Mawes, South Cornwall.
  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £1002

Port and Starboard

5982

4 bedroom holiday cottage with sea views in St Mawes, South Cornwall.


In prime position overlooking St Mawes Bay with wonderful seascape views, beautiful interiors and gorgeous contemporary furnishings, semi-detached Port and Starboard is a fabulous ...

  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £1002

View
  • 10% off

    20 Sep 2025 - 27 Sep 2025

    From £1272.00 £1144.80

Hobbit Corner is a 1 bedroom, dog friendly holiday cottage near Looe, South Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £421

Hobbit Corner

5959

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


Wind your way along the leafy lanes to the peaceful hamlet of Trevelmond, in the heart of southeast Cornwall, where this little beauty is waiting to welcome you with open arms and ...

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

7 nights from £421

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

Roselands is a 4 bedroom, dog friendly cottage with sea views in Mullion, Cornwall.
  • Sleeps 8 + 3 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £1114 *

Roselands

5989

4 bedroom, dog friendly cottage with sea views in Mullion, Cornwall.


A thoughtful and imaginative renovation has completely transformed this once humble bungalow into an spacious and elegant four-bedroom sanctuary, perfectly placed on Cornwall's rug...

  • Sleeps 8 + 3 cots
  • Dogs welcome
  • Changeover Thu

7 nights from £1114 *

View
  • 10% off

    16 Oct 2025 - 23 Oct 2025

    From £1363.00 £1226.70

Brookfield is a 3 bedroom, dog friendly cottage near Callington, South Cornwall.
  • Sleeps 8 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £1117 *

Brookfield

5999

3 bedroom, dog friendly cottage near Callington, South Cornwall.


Looking for a very special escape to the country, surrounded by open farmland, where peace and tranquility reign supreme, then look no further than Brookfield. Nestled on the edge ...

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

7 nights from £1117 *

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.