Holiday cottages for September in Sussex

Holiday cottages for September in Sussex

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

Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.

We have 22 Sussex holiday cottages available in September.

Carter's Cottage is a 1 bedroom self catering cottage near Hailsham.
  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £491

Carter's Cottage

6005

1 bedroom self catering cottage near Hailsham.


This cosy and well-appointed semi-detached country retreat sits on a working heavy horse farm, perfect for couples or solo travellers looking to unwind, reconnect and enjoy the slo...

  • Sleeps 2
  • No pets
  • Changeover Fri

7 nights from £491

Little Oak Farm

  • Sleeps 6 in 3 properties
  • Changeover Fri

7 nights from £256

Isla Rose is a Dog friendly shepherds hut near Pulborough.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

From £85 per night

Isla Rose

5948

Dog friendly shepherds hut near Pulborough.


This oh-so-romantic shepherd's hut for two lies in the beautiful countryside of West Sussex and offers an idyllic, peaceful escape that's dog friendly too. Just a mere two hours...

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

From £85 per night

Hayesland Lodge is a 1 bedroom, dog friendly self catering cottage near Rye.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Sat

7 nights from £630

Hayesland Lodge

5700

1 bedroom, dog friendly self catering cottage near Rye.


This gem is situated in a peaceful and tranquil setting in a National Landscape (an Area of Outstanding Natural Beauty) with farmland views, a short drive from the coast and the me...

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

7 nights from £630

Beacon Hill Barn is a 2 bedroom self catering cottage near Midhurst.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £939

Beacon Hill Barn

5644

2 bedroom self catering cottage near Midhurst.


This gorgeous barn sits in the heart of the South Downs National Park providing an excellent base for all types of rural pursuits and is perfectly positioned for visiting the towns...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £939

Matilda is a 1 bedroom, dog friendly self catering cabin near Battle.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

From £82 per night

Matilda

5380

1 bedroom, dog friendly self catering cabin near Battle.


This wonderful enchanting medieval-styled cabin is only a couple of hours from London, situated on land that was once part of the Battle Abbey Estate in 1066 country. If you're loo...

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

From £82 per night

Pickeridge Barn is a 6 bedroom, dog friendly self catering home near Haywards Heath.
  • Sleeps 14 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1570 *

Pickeridge Barn

5216

6 bedroom, dog friendly self catering home near Haywards Heath.


This newly converted and eco-friendly barn is rather unique, the perfect holiday home for those looking for a multi-family getaway in the heart of the Sussex countryside. Situat...

  • Sleeps 14 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1570 *

Cala Lily is a Dog friendly shepherds hut near Pulborough.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

From £85 per night

Cala Lily

5289

Dog friendly shepherds hut near Pulborough.


With countryside views and just two hours from London, Cala Lily is a luxury shepherd's hut situated in the beautiful countryside of West Sussex and offers a dreamy escape where yo...

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

From £85 per night

Choose our flexible booking option and have the ability to cancel anytime.

Douglas Fir is a Dog friendly shepherds hut near Pulborough.
  • Sleeps 2
  • Dogs welcome (1 only)
  • Changeover Fri

From £85 per night

Douglas Fir

5290

Dog friendly shepherds hut near Pulborough.


Hidden away in the West Sussex countryside yet just two hours from London, this luxury shepherd's hut offers a magical escape for two. Beautiful and handcrafted, it has all you ...

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

From £85 per night

South Barn at Pickeridge is a 3 bedroom, dog friendly self catering cottage near Haywards Heath.
  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1074

South Barn at Pickeridge

5211

3 bedroom, dog friendly self catering cottage near Haywards Heath.


South Barn at Pickeridge is tucked away on a 120 acre working farm in a secluded valley between West Hoathly and Ardingly. It's the perfect retreat for families and friends looking...

  • Sleeps 7 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1074

Load 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 22 holiday cottages in Sussex available for your September break.