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

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. 

Isle of Wight Ferry Booking Our exclusive ferry discounts will make your island trip with Classic plain sailing.

We have 1033 holiday cottages available in September

The Dream is a 2 bedroom luxury apartment with panoramic sea views in Praa Sands, West Cornwall.
  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £1105

The Dream

3847

2 bedroom luxury apartment with panoramic sea views in Praa Sands, West Cornwall.


The breathtaking view from this stunning beach apartment must be one of the best in Cornwall; imagine relaxing on your private balcony at the end of another wonderful day watching ...

  • Sleeps 4 + cot
  • No pets
  • Changeover Sat

7 nights from £1105

Lavender Barn is a 2 bedroom, rural retreat near Porthleven, West Cornwall.
  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £888

Lavender Barn

4010

2 bedroom, rural retreat near Porthleven, West Cornwall.


This delightful property is surrounded by rolling hills and wonderful countryside just a mile from the picturesque harbour town of Porthleven and the ancient market town of Helston...

  • Sleeps 4
  • No pets
  • Changeover Fri

7 nights from £888

Yew Tree Cottage is a 2 bedroom, dog friendly cottage near the sea near Torpoint, Cornwall.
  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £747

Yew Tree Cottage

4008

2 bedroom, dog friendly cottage near the sea near Torpoint, Cornwall.


Fall in love with the beauty and charm of Mount Edgcumbe at this absolute gem of a cottage. Originally built in the early 1900s this immaculate semi-detached cottage has been beaut...

  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £747

5 Dart Marina is a 2 bedroom holiday apartment with sea views in Dartmouth, South Devon.
  • Sleeps 4
  • No pets
  • Changeover Thu

7 nights from £1911

5 Dart Marina

4002

2 bedroom holiday apartment with sea views in Dartmouth, South Devon.


This beautiful apartment is superb from every angle. Perched overhanging the River Dart, the view of the stunning Dart Marina is unrivalled; fling open the patio doors and prepare ...

  • Sleeps 4
  • No pets
  • Changeover Thu

7 nights from £1911

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

Chyandour is a 3 bedroom, dog friendly cottage with sea views near St Mawes.
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £618 *

Chyandour

3966

3 bedroom, dog friendly cottage with sea views near St Mawes.


There are fabulous views over the sailing waters around St Mawes from both the garden and first floor living-room of this contemporary eco-house, set on the edge of St Just in Rose...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £618 *

Moorland View is a 1 bedroom, dog friendly cottage near the beach in St Just, Cornwall.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £604

Moorland View

3973

1 bedroom, dog friendly cottage near the beach in St Just, Cornwall.


Stunningly gorgeous, this former miner's terraced cottage has been transformed into a beautiful retreat for couples looking for something extra special. Tucked away in the lovely f...

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

7 nights from £604

Church Lane Cottage is a 2 bedroom, dog friendly cottage near Polzeath, North Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £762

Church Lane Cottage

3987

2 bedroom, dog friendly cottage near Polzeath, North Cornwall.


Set in the peaceful hamlet of St Minver yet only two miles from the thrills and delights of trendy Rock and Polzeath, Church Lane Cottage is a little beauty! Wonderfully welcoming ...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £762

St Albans House is a 4 bedroom self catering cottage with sea views near Ventnor, Isle of Wight
  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1036

St Albans House

3980

4 bedroom self catering cottage with sea views near Ventnor, Isle of Wight


This large detached house is situated in an elevated position as you enter the town of Ventnor, with the most breathtaking views from virtually every room. The beautiful tiered...

  • Sleeps 8 + cot
  • No pets
  • Changeover Fri

7 nights from £1036

Little St Hugh is a 1 bedroom holiday cottage near the sea in Boscastle, North Cornwall.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £502

Little St Hugh

3969

1 bedroom holiday cottage near the sea in Boscastle, North Cornwall.


Packed with character, charm and comfort, Little St Hugh is a cosy retreat for two, tucked away in the pretty village of Boscastle – it will have you leaving your worries behind fr...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £502

Flackstead is a 3 bedroom self catering cottage near the beach in Brook, Isle of Wight
  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2544

Flackstead

3913

3 bedroom self catering cottage near the beach in Brook, Isle of Wight


Flackstead is a unique eco-friendly house which has breathtaking and uninterrupted coastal views across Compton Bay towards the Needles. Flackstead combines the very best of co...

  • Sleeps 6 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £2544

Be in the know… Sign up to our newsletter for holiday inspiration, offers and all things Classic.

Loading more