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. 

Our exclusive ferry discounts will make your island trip with Classic plain sailing.

We have 1164 holiday cottages available in September

Olive is a Shepherd's hut with wood-fired outdoor bath in South Devon.
  • Sleeps 2
  • No pets
  • Changeover Fri

From £92 per night

Olive

5755

Shepherd's hut with wood-fired outdoor bath in South Devon.


Nestled in a tranquil meadow on the edge of Dartmoor National Park, Olive is a charming shepherd's hut, perfect for blissful days and star gazing nights surrounded by nature. For t...

  • Sleeps 2
  • No pets
  • Changeover Fri

From £92 per night

Llanamor is a Stunning 3 bedroom homestay with sea views nr Whitsand Bay, South Cornwall.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £1254

Llanamor

5789

Stunning 3 bedroom homestay with sea views nr Whitsand Bay, South Cornwall.


Come and fall under the spell of our stunning coastal retreat, set on the gorgeous Rame peninsula in the tiny hamlet of Portwrinkle. With endless sea views, incredible interiors an...

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £1254

Low Shaw Farmhouse is a 4 bedroom, dog friendly self catering cottage in Hawes.
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1092 *

Low Shaw Farmhouse

5794

4 bedroom, dog friendly self catering cottage in Hawes.


As you approach the hamlet of Simonstone and look up to the hill on your right you will see Low Shaw Farmhouse nestled on the hillside, surrounded by sheep enclosed by the wonderfu...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £1092 *

Hendy Cottage is a 3 bedroom, dog friendly self catering cottage in Stroud.
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1135

Hendy Cottage

5793

3 bedroom, dog friendly self catering cottage in Stroud.


Hendy Cottage is a charming end of terrace, Grade II Listed Cotswold stone cottage situated just moments from Rodborough Common, offering stunning views over the Cotswold Way and t...

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

7 nights from £1135

Sancia is a 2 bedroom, dog friendly cottage near the beach near Hunstanton.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £755

Sancia

5759

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


This stylish bungalow offers a comfortable retreat on the renowned Peddars Way in the heart of the village of Holme-next-the-Sea. Just a minute's stroll from the fabulous local p...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £755

Joe House is a 2 bedroom self catering cottage near Hawes.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £612

Joe House

5779

2 bedroom self catering cottage near Hawes.


Once inside you will be enveloped in the essence of a Yorkshire country cottage with beams, hand hewn staircase, walls which have been carefully renovated to ensure the traditiona...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £612

Nettlebed is a 3 bedroom, dog friendly self catering cottage near Hawes.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £844

Nettlebed

5768

3 bedroom, dog friendly self catering cottage near Hawes.


Come away to Yorkshire and experience the authentic, rustic charm of an original Yorkshire stone cottage. Nettlebed is nestled on the hillside with amazing views over Swaledale and...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £844

Hartland Cottage is a 3 bedroom, dog friendly cottage near the sea in Boscastle, Cornwall.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £567

Hartland Cottage

5777

3 bedroom, dog friendly cottage near the sea in Boscastle, Cornwall.


Bursting with charm and character, this Grade II Listed terraced cottage is a terrific getaway for families, couples, walkers and dog lovers wanting to explore this enchanting part...

  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £567

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

Yew Tree Barn is a 2 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £688

Yew Tree Barn

5784

2 bedroom, dog friendly holiday cottage near Glastonbury, Somerset.


Situated in a peaceful corner of Somerset, with uninterrupted countryside views across the Levels, Yew Tree Barn is a high quality barn conversion with a contemporary feel. Perfect...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £688

5 Green Edge is a 4 bedroom, dog friendly town house with sea views in Beaumaris.
  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £900

5 Green Edge

5787

4 bedroom, dog friendly town house with sea views in Beaumaris.


Set along the picturesque Anglesey coastline, 5 Green Edge is a substantial three-storey, Grade II Listed Georgian home blending historic charm with modern comfort. Step inside int...

  • Sleeps 8 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £900

Loading more