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 1388 holiday cottages available in September

Surby Mount is a A delightful rural setting near Port Erin, ideal for families.
  • Sleeps 7 + 2 cots
  • Dogs welcome

Surby Mount

204

A delightful rural setting near Port Erin, ideal for families.


Surby Mount is a beautifully appointed countryside retreat tucked away in the peaceful Surby, just a few minutes from the coastal village of Port Erin. Surrounded by rolling farmla...

  • Sleeps 7 + 2 cots
  • Dogs welcome
Solas is a Beautiful lochside cabin situated in coastal woodland near Ullapool, Scottish Highlands.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

From £150 per night *

Solas

6111

Beautiful lochside cabin situated in coastal woodland near Ullapool, Scottish Highlands.


Tucked away between towering pines, you’ll find Solas, a purpose-built cabin with envious views across Loch Broom and the perfect stay for families. The cabin’s dark exterior c...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

From £150 per night *

Silva is a Beautiful lochside cabin situated in coastal woodland near Ullapool, Scottish Highlands.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £128 per night

Silva

6110

Beautiful lochside cabin situated in coastal woodland near Ullapool, Scottish Highlands.


Nestled between the trees on the edge of Leckmelm Wood, on the North Coast 500 route, Silva offers the ultimate peaceful retreat for two. Purpose-built with dark exterior cladd...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £128 per night

Ocean View at 32 is a 2 bedroom, dog friendly apartment with sea views in Saundersfoot.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £656

Ocean View at 32

6129

2 bedroom, dog friendly apartment with sea views in Saundersfoot.


Wake up to the soothing sound of the sea in Ocean View at 32. You'll fall in love with the glorious Blue Flag beach and uninterrupted, far reaching sea views from this sweet little...

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

7 nights from £656

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British Travel Awards 2025
Best company for UK holiday home rentals

Little Field is a 3 bedroom, dog friendly holiday cottage near the beach near Ryde.
  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £851 *

Little Field

6123

3 bedroom, dog friendly holiday cottage near the beach near Ryde.


Tucked away on a quiet road, Little Field has been lovingly built by the owners and offers guests a peaceful and tranquil retreat with oodles of space and modern living. Situated o...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £851 *

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
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

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

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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.