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 1387 holiday cottages available in September

Dormy House is a 3 bedroom, dog friendly holiday cottage near the beach in Hunstanton.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1275

Dormy House

6084

3 bedroom, dog friendly holiday cottage near the beach in Hunstanton.


Dormy House is single-storey beach house, nestled in an idyllic spot, just moments away from the stunning beaches of this much-loved village, along the north west Norfolk coastline...

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

7 nights from £1275

The Bothy is a 1 bedroom, dog friendly self catering cottage near Skipton.
  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £582

The Bothy

6125

1 bedroom, dog friendly self catering cottage near Skipton.


If you are craving a cosy getaway for two or a quiet friend's weekend, The Bothy is a great choice. It is a traditional, restored stone cottage sitting right in the heart of the de...

  • Sleeps 2
  • Dogs welcome
  • Changeover Fri

7 nights from £582

The Retreat is a 5 bedroom, dog friendly self catering cottage near Crickhowell.
  • Sleeps 10 + 2 cots
  • Dogs welcome
  • Changeover Fri

From £900 per night

The Retreat

6121

5 bedroom, dog friendly self catering cottage near Crickhowell.


The spellbinding beauty of the Bannau Brycheiniog (Brecon Beacons) are calling you for your next celebration or larger get-together. Escape to the hills at the exquisite The Retrea...

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

From £900 per night

12 Castle Street is a 4 bedroom, dog friendly self catering cottage near Ruthin.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1120 *

12 Castle Street

6130

4 bedroom, dog friendly self catering cottage near Ruthin.


Step into a world of timeless elegance and sheer comfort in 12 Castle Street, where classic charm meets modern luxury and pure relaxation. Escape to this superbly renovated Victori...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1120 *

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British Travel Awards 2025
Best company for UK holiday home rentals

Mount View Cottage is a 3 bedroom, dog friendly cottage with sea views in Marazion, Cornwall.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £862 *

Mount View Cottage

6128

3 bedroom, dog friendly cottage with sea views in Marazion, Cornwall.


Tucked away along a narrow Cornish lane in the heart of Marazion, Mount View Cottage is a delightful coastal retreat with sweeping views across Mount's Bay towards the iconic St Mi...

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

7 nights from £862 *

Caban Tarren is a Cabin in Wales with wood-burner and outdoor kitchen.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £585

Caban Tarren

6115

Cabin in Wales with wood-burner and outdoor kitchen.


Full of charm and soul, this cabin nestled in the heart of the Welsh countryside offers the ultimate escape, surrounded only by rolling hills and mountain views – dreamy. Built...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £585

Harecroft is a 4 bedroom, dog friendly cottage near the beach in Old Hunstanton.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £1020

Harecroft

6097

4 bedroom, dog friendly cottage near the beach in Old Hunstanton.


Harecroft is a single-storey holiday home, set within generous gardens and sleeping up to six guests across four bedrooms. Nestled within a quiet, leafy lane in one of Norfolk's mo...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £1020

Rycroft House is a Where light, space, and coastal calm meet in style
  • Sleeps 6 + 2 cots
  • Dogs welcome

Rycroft House

205

Where light, space, and coastal calm meet in style


Tucked away at the top of a quiet cul-de-sac in the heart of Laxey, Rycroft House is a striking contemporary retreat where thoughtful architecture and coastal calm come together ef...

  • Sleeps 6 + 2 cots
  • Dogs welcome
La Cabana is a 3 bedroom cottage with sea views in Portscatho, South Cornwall.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £855

La Cabana

6102

3 bedroom cottage with sea views in Portscatho, South Cornwall.


Portscatho is a rather charming coastal village on the Roseland peninsula with gorgeous views over Gerrans Bay, easy access to the wonderful coast path and a vibrant centre with a ...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £855

Oak Tree House is a 4 bedroom, dog friendly holiday cottage near Dorchester, Dorset.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1599 *

Oak Tree House

6112

4 bedroom, dog friendly holiday cottage near Dorchester, Dorset.


Oak Tree House is a particularly special property for gathering friends and family (plus the four-legged variety) together. Set in stunning grounds in the little village of Frampto...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1599 *

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

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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.