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 34 Sussex holiday cottages available in September.

The Old Tractor Shed is a 2 bedroom, dog friendly self catering cottage near Winchelsea.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £788 booking fees included

The Old Tractor Shed

6180

2 bedroom, dog friendly self catering cottage near Winchelsea.


Tucked away on a working sheep farm close to the coast and the medieval towns of Rye and Winchelsea, this peaceful escape is surrounded by beautiful farmland and scenic footpaths i...

  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £788

Bloomsbury Cottage is a 1 bedroom, dog friendly self catering cottage in Wadhurst.
  • Sleeps 2 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £618 booking fees included

Bloomsbury Cottage

6186

1 bedroom, dog friendly self catering cottage in Wadhurst.


For a digital detox head to the beautiful countryside of the High Weald National Landscape to stay at this unique timber-cladded barn that offers a peaceful escape just moments fro...

  • Sleeps 2 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £618

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Broyle Cottage is a 3 bedroom, dog friendly self catering cottage near Hailsham.
  • Sleeps 6
  • Dogs welcome
  • Changeover Fri

7 nights from £809 * booking fees included

Broyle Cottage

6174

3 bedroom, dog friendly self catering cottage near Hailsham.


Tucked away in a peaceful hamlet near the village of Herstmonceux, this quintessential English country cottage lends itself to family gatherings, celebrations or romantic breaks. B...

  • Sleeps 6
  • Dogs welcome
  • Changeover Fri

7 nights from £809 *

Bramley Lodge is a 1 bedroom self catering cottage near Heathfield.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £85 per night + £63 booking fees

Bramley Lodge

6137

1 bedroom self catering cottage near Heathfield.


Soak up the scenic views of this enchanting lodge that sits within an orchard in the High Weald National Landscape. Its peaceful location is the perfect escape for a romantic getaw...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

From £85 per night

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Dunks Cottage is a 4 bedroom, dog friendly self catering cottage near Cranbrook.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1329 booking fees included

Dunks Cottage

6074

4 bedroom, dog friendly self catering cottage near Cranbrook.


Overlooking the village green of Sandhurst, Kent, in the beautiful High Weald National Landscape (Area of Outstanding Natural Beauty), this wonderfully spacious, semi-detached cott...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1329

Nobby Nook is a 1 bedroom, dog friendly self catering cottage near Battle.
  • Sleeps 2 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Thu

7 nights from £720 booking fees included

Nobby Nook

6006

1 bedroom, dog friendly self catering cottage near Battle.


This characterful gem, nestled in beautiful Sussex countryside, offers the perfect retreat for couples and solo travellers seeking a luxury escape. Nobby Nook is a lovingly conv...

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

7 nights from £720

Austin House is a 3 bedroom self catering cottage near the beach in Worthing.
  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £944 booking fees included

Austin House

6019

3 bedroom self catering cottage near the beach in Worthing.


Situated in the heart of Worthing, just a short walk from the seafront with its long promenade and Victorian pier, this spacious house is perfect for family get-togethers and those...

  • Sleeps 6 + 2 cots
  • No pets
  • Changeover Fri

7 nights from £944

Pomona Annexe is a 2 bedroom, dog friendly self catering cottage in Battle.
  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £788 booking fees included

Pomona Annexe

6053

2 bedroom, dog friendly self catering cottage in Battle.


Located just a short drive from the stunning Sussex coast and a short ten-minute walk to the RSPB Fore Wood Nature Reserve and the iconic town of Battle, Pomona Annexe is a charmin...

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

7 nights from £788

Rockfield Lodge is a 3 bedroom, dog friendly self catering cottage near Battle.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1064 booking fees included

Rockfield Lodge

6054

3 bedroom, dog friendly self catering cottage near Battle.


Situated in beautiful grounds just outside the medieval town of Battle and a short drive from Hastings and St Leonards-on-Sea, this delightful lodge offers a spacious holiday abode...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1064

Ellenhall is a 4 bedroom, dog friendly self catering cottage near Battle.
  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1946 booking fees included

Ellenhall

5990

4 bedroom, dog friendly self catering cottage near Battle.


Escape to this picture-perfect countryside retreat which sits in a salubrious location in the High Weald National Landscape (Area of Outstanding Natural Beauty). Surrounded by anci...

  • Sleeps 8 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £1946

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

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 34 holiday cottages in Sussex available for your September break.