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. 

We have 972 holiday cottages available in September

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £364

Little Chi Argel

4879

1 bedroom self catering apartment near Bodmin, North Cornwall.


Escape to the delights of Little Chi Argel to enjoy rambles across open moorland, thrilling days on the coast and the chance to immerse yourself in village life. This spacious and ...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £364

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

7 nights from £365 *

Winwalloe Cottage

3774

2 bedroom, dog friendly, rural holiday cottage near Looe, South Cornwall.


Tucked down a leafy lane with birdsong in the air, the rural tranquility of this pretty semi-detached cottage will delight those looking for a break from busy daily lives. Just...

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

7 nights from £365 *

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £372

Jordan Vale

2135

1 bedroom apartment near the sea in Boscastle, North Cornwall.


With a bird's eye view overlooking Boscastle's picturesque Jordan Vale, this charming little bolthole for two is a great base for exploring the delights of this lovely village and ...

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £372

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £375

The Beatrice Studio

3666

1 bedroom self catering apartment near the beach in Shanklin, Isle of Wight.


Located on the first floor of Shanklin Villa, a lovely Victorian property, this small studio apartment packs a punch despite its size. Enjoying beautiful sea views from its elevate...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £375

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

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £376 *

Springfield

4928

2 bedroom holiday cottage near Crackington Haven, North Cornwall.


Nestled in secluded gardens and surrounded by gorgeous countryside and working farms, Springfield is a beautifully kept single-storey dwelling and perfect for walkers looking to ex...

  • Sleeps 4 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £376 *

View
  • 10% off

    20 May 2022 - 27 May 2022

    £641.20 £576.90

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

7 nights from £377 *

Lee Cottage

3842

2 bedroom, dog friendly, rural holiday cottage near Looe, South Cornwall.


What a delightful getaway this is, set down a tree-lined lane amid the tranquility of beautiful countryside. With rustling leaves and birdsong as a background lullaby, you will rel...

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

7 nights from £377 *

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £377

The Garden Flat

3264

1 bedroom apartment near the beach in Penzance, West Cornwall.


Overlooking the beautiful sub-tropical Morrab Gardens and just a short stroll from Penlee House Gallery and the wonderful Penzance promenade, The Garden Flat is the perfect base fo...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Sat

7 nights from £377

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £383

Little Tregerry

3859

1 bedroom, rural holiday cottage near Launceston, North Cornwall.


If you're looking for a peaceful break for two, you need look no further than Little Tregerry. Located down a country lane, in the heart of the Cornish countryside, this is the per...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £383

View
  • 10% off

    20 May 2022 - 27 May 2022

    £427.50 £385.20

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £385

The Workshop

2245

1 bedroom, rural holiday cottage near Falmouth, West Cornwall.


This delectably simple little pied-a-terre, set midway between both coasts, makes an ideal base for exploring Cornwall. The private south-facing garden, with its handy shed for ...

  • Sleeps 2
  • Regret no pets
  • Changeover Sat

7 nights from £385

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

7 nights from £386

Viewtown Linhay

4500

1 bedroom, dog friendly apartment near Callington, South Cornwall.


Viewtown Linhay is a hidden gem offering a walker's paradise for you and your hound. Situated in the Tamar Valley bordering the Area of Outstanding Natural Beauty on the outskirts ...

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

7 nights from £386

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

Loading more