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 1391 holiday cottages available in September

Spring Cottage is a A cosy hideaway overlooking Port Erin and the south
  • Sleeps 3 + cot
  • No pets

Spring Cottage

203

A cosy hideaway overlooking Port Erin and the south


Welcome to Spring Cottage, a beautifully refurbished self-catering holiday cottage set high above Port Erin and Port St Mary on Ballakillowey in the scenic south of the Isle of Man...

  • Sleeps 3 + cot
  • No pets
Kipper Cottage is a Cosy Peel cottage by the sea, perfect for sunset evenings
  • Sleeps 3 + cot
  • No pets

Kipper Cottage

202

Cosy Peel cottage by the sea, perfect for sunset evenings


Kipper Cottage is a beautifully refurbished coastal hideaway in the heart of Peel, offering an indulgent blend of contemporary comfort and homely charm just moments from the town’s...

  • Sleeps 3 + cot
  • No pets
Abbey at Trail Lodge is a Stylish studio apartment located in an idyllic national glen.
  • Sleeps 2
  • Dogs welcome

Abbey at Trail Lodge

174

Stylish studio apartment located in an idyllic national glen.


Abbey at Trail Lodge is a modern self-catering studio apartment set within the beautifully restored Silverdale Corn Mill, surrounded by the peaceful Silverdale Glen near Ballasalla...

  • Sleeps 2
  • Dogs welcome
Silverburn at Trail Lodge is a Stylish studio apartment located in an idyllic national glen.
  • Sleeps 2
  • Dogs welcome

Silverburn at Trail Lodge

170

Stylish studio apartment located in an idyllic national glen.


Silverburn at Trail Lodge is a modern self-catering studio apartment set within the beautifully restored Silverdale Corn Mill, surrounded by the peaceful Silverdale Glen near Balla...

  • Sleeps 2
  • Dogs welcome
British Travel Awards 2025 - Best Company For UK Holiday Home Rentals Logo

British Travel Awards 2025
Best company for UK holiday home rentals

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

7 nights from £447

The Gallery

6127

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


A cosy, rural retreat for two and a small dog; nestled in the Cornish countryside but only a 10 minute drive to the stunning north coast and a short drive to the city of Truro. Set...

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

7 nights from £447

Rose End Cottage is a 3 bedroom, dog friendly holiday cottage near Padstow, North Cornwall.
  • Sleeps 5
  • Dogs welcome
  • Changeover Fri

7 nights from £670 *

Rose End Cottage

6073

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


Treat yourself to a well deserved break at this gem of a cottage, nestled on the edge of the village of St Issey and perfectly placed for discovering the very best of north Cornwal...

  • Sleeps 5
  • Dogs welcome
  • Changeover Fri

7 nights from £670 *

Y Beudy is a 4 bedroom, dog friendly cottage with sea views near St Davids.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £800

Y Beudy

6107

4 bedroom, dog friendly cottage with sea views near St Davids.


With far reaching, uninterrupted, spectacular sea views, set in eight acres of countryside and expansive lawns, gorgeous, stone-built Y Beudy is a charming conversion of a traditio...

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

7 nights from £800

Ysgubor is a 2 bedroom, dog friendly cottage with sea views near St Davids.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £600

Ysgubor

6106

2 bedroom, dog friendly cottage with sea views near St Davids.


Nestling in the magnificent glory of the dramatic, rugged Pembrokeshire coastline, offering golden beaches, crystal blue sea and pretty seaside villages, dog-friendly, Ysgubor (Gra...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £600

Mount Folly Farmhouse is a 3 bedroom, dog friendly cottage with sea views near Kingsbridge.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1326

Mount Folly Farmhouse

6108

3 bedroom, dog friendly cottage with sea views near Kingsbridge.


Welcoming you to Mount Folly Farmhouse, a fabulous retreat which enjoys both coast and country. On entering Mount Folly Farmhouse you will feel immediately at home, this spacious y...

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

7 nights from £1326

Mount Folly Penthouse is a 3 bedroom apartment with sea views near Kingsbridge, South Devon.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1326

Mount Folly Penthouse

6109

3 bedroom apartment with sea views near Kingsbridge, South Devon.


If you're looking for a beautifully finished penthouse apartment, boasting the most spectacular views from almost every window, a glorious hot tub and outdoor sauna perched overloo...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1326

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

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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.