Holiday cottages for September in South West

Holiday cottages for September in South West

If Septembers past are anything to go by, this is often one of the loveliest months to enjoy a holiday cottage in South West.Read more

The beaches are still peachy, the sea's had all summer to warm up and the schools have gone back. So you can have more sand, more cliffs and more moor to yourself. Use the search options on the left to choose your holiday dates. We've got 877 holiday cottages in South West available for your September break.

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

We have 877 South West holiday cottages available in September.

The Dairy is a 2 bedroom, dog friendly holiday cottage near Beaminster, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £530

The Dairy

5682

2 bedroom, dog friendly holiday cottage near Beaminster, Dorset.


A cosy single-storey cottage, a secret wood and wildflower meadow, all available to you in a location only a short drive of the World Heritage Jurassic Coast, are we tempting you y...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £530

River View Terrace is a 3 bedroom holiday cottage with sea views near Fowey, South Cornwall.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £756

River View Terrace

5667

3 bedroom holiday cottage with sea views near Fowey, South Cornwall.


Come and treat yourself to a wonderful holiday in the peaceful creekside village of Golant on the banks of the River Fowey. With the most gorgeous views of the tidal waters over to...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £756

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

Valley View is a 2 bedroom, dog friendly holiday cottage near Newquay, North Cornwall.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £727

Valley View

5671

2 bedroom, dog friendly holiday cottage near Newquay, North Cornwall.


A stylish, dog-friendly bolthole with far reaching views over the valley and the added luxury of a hot tub, what more could you want from your holiday? This special property is loc...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £727

Riverwood is a 3 bedroom holiday cottage near the sea in Boscastle, North Cornwall.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £936

Riverwood

5661

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


For scenery-packed coastal walks, exploring fishing villages and historic harbours, as well as fun days on some fabulous beaches, this idyllic haven is just the ticket for a great ...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £936

Reservoir Cottage is a 3 bedroom, dog friendly cottage near the beach near St Ives.
  • Sleeps 6 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £767 *

Reservoir Cottage

5692

3 bedroom, dog friendly cottage near the beach near St Ives.


If escapism is required, then Reservoir Cottage will not disappoint. Nestled in the Cornish countryside, only a mile away from the bustling harbour of St Ives and its many sandy be...

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

7 nights from £767 *

The Clock House is a 4 bedroom holiday cottage with sea views near Truro, South Cornwall.
  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £2200

The Clock House

5533

4 bedroom holiday cottage with sea views near Truro, South Cornwall.


This fabulous abode is a real home-from-home with the most fabulous views, beautiful walled garden and access to a private beach. What more could you ask for? This beautiful Grade ...

  • Sleeps 8 + cot
  • No pets
  • Changeover Sat

7 nights from £2200

Stable End is a 1 bedroom, dog friendly self catering cottage near Chippenham.
  • Sleeps 2 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £607

Stable End

5648

1 bedroom, dog friendly self catering cottage near Chippenham.


Located in Grittleton, a short drive from both Chippenham and Bath, just on the edge of the Cotswolds, an area of beautiful countryside and picturesque villages, come and discover ...

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

7 nights from £607

Weighbridge Barn

  • Sleeps 4 + 4 cots in 2 properties
  • Changeover Fri

7 nights from £1282

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

Weighbridge End is a 1 bedroom, dog friendly self catering cottage near Chippenham.
  • Sleeps 2 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £675

Weighbridge End

5647

1 bedroom, dog friendly self catering cottage near Chippenham.


This stunning barn located on the edge of the Cotswolds is a gem of a property just waiting to be discovered. Sympathetically converted with nods to its previous life as a working ...

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

7 nights from £675

65 Lower Maen Cottage is a 3 bedroom cottage with sea views near Falmouth, South Cornwall.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £990

65 Lower Maen Cottage

5597

3 bedroom cottage with sea views near Falmouth, South Cornwall.


Welcome to this lovely, light-filled holiday home with delightful sea views, situated just a short stroll away from a pretty, sandy cove and the harbourside town of Falmouth. Set i...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £990

Loading more