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 737 holiday cottages available in September

Ballachrink Barn is a
  • Sleeps 4 + cot
  • Dogs welcome

Ballachrink Barn

222


Ballachrink Barn is a beautifully presented self-catering holiday cottage located in the peaceful village of Glen Maye on the west coast of the Isle of Man, just south of Peel. ...

  • Sleeps 4 + cot
  • Dogs welcome
Ruska is a Luxury cabin for two with an outdoor bath, privately nestled in the Forest of Dean.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £929 booking fees included

Ruska

6209

Luxury cabin for two with an outdoor bath, privately nestled in the Forest of Dean.


Sitting in the Gloucestershire countryside, this lakeside retreat for two offers a peaceful and romantic getaway. This gorgeous cabin has been lovingly handcrafted with luxury in m...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £929

Reserve your 2027 holiday for just £40.00

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Greystones at Ago's Leap is a Impressive Douglas home with private gardens and tennis court
  • Sleeps 6 + 2 cots
  • Dogs welcome

Greystones at Ago's Leap

221

Impressive Douglas home with private gardens and tennis court


Set along Quarterbridge Road in Douglas, Greystones is a striking and spacious home offering an impressive place to stay within easy reach of the Island's capital. Beautifully p...

  • Sleeps 6 + 2 cots
  • Dogs welcome
Goaf Cottage is a 2 bedroom, dog friendly self catering cottage near Whitby.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £905 booking fees included

Goaf Cottage

6204

2 bedroom, dog friendly self catering cottage near Whitby.


In a county of hills, dales and sandy beaches, you will find the moors village of Glaisdale and nestled in a sleepy lane sits Goaf Cottage, an old farm building converted into a go...

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

7 nights from £905

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Ballacosney Cottage is a Stylish Laxey cottage with private gym and sauna
  • Sleeps 6 + cot
  • No pets

Ballacosney Cottage

219

Stylish Laxey cottage with private gym and sauna


Tucked away up a peaceful lane above Laxey, Ballacosney Cottage is a beautifully renovated retreat designed with relaxing island stays in mind. Fresh, modern and filled with natura...

  • Sleeps 6 + cot
  • No pets
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Hooper's House is a 4 bedroom self catering cottage in Gloucester.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £1348 booking fees included

Hooper's House

6203

4 bedroom self catering cottage in Gloucester.


Hooper's House is a centuries-old property sitting in harmony with the historic buildings of Gloucester Cathedral but with a contemporary interior vibe, mixing traditional and mode...

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

7 nights from £1348

St Peter's House is a 2 bedroom self catering cottage in Gloucester.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £1067 booking fees included

St Peter's House

6202

2 bedroom self catering cottage in Gloucester.


Set within Gloucester Cathedral's grounds with a magnificent glimpse of the Cathedral spires from the impressive staircase, St Peter's House enjoys a truly amazing location. A hous...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £1067

Round Table House is a A unique countryside retreat with breathtaking southern views
  • Sleeps 8 + cot
  • Dogs welcome

Round Table House

218

A unique countryside retreat with breathtaking southern views


Round Table House stands high above the rolling countryside of Ronague, a remarkable retreat where contemporary style meets the character of a much-loved home. Its elevated positio...

  • Sleeps 8 + cot
  • Dogs welcome
Hawcombe Cottage is a 1 bedroom, dog friendly cottage with sea views near Tavistock.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £624 booking fees included

Hawcombe Cottage

6205

1 bedroom, dog friendly cottage with sea views near Tavistock.


Tucked away in the pretty riverside village of Bere Ferrers, Hawcombe Cottage is a charming hideaway for two, perfectly placed for those seeking a peaceful escape surrounded by the...

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

7 nights from £624

April Cottage is a 2 bedroom, dog friendly cottage near the beach near Coverack.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Thu

7 nights from £658 booking fees included

April Cottage

6199

2 bedroom, dog friendly cottage near the beach near Coverack.


Tucked away in an historic beachside location, this chic yet characterful semi-detached cottage has been lovingly restored and brought back to life, creating the perfect escape for...

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

7 nights from £658

Need more time? Reserve any cottage for up to 24 hours before booking.

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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.