Holiday cottages for September in South England

Holiday cottages for September in South England

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

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

We have 94 South England 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 £668 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 £668

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  • 20% off

    23 Sep 2026 - 26 Sep 2026

    £570.50 £469.00 booking fees included

  • 20% off

    2 Oct 2026 - 5 Oct 2026

    £555.80 £457.24 booking fees included

  • 20% off

    9 Oct 2026 - 16 Oct 2026

    £746.00 £609.40 booking fees included

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

7 nights from £619 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 £619

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St Hubert's Lodge is a 3 bedroom, dog friendly self catering cottage near Yarmouth.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1352 booking fees included

St Hubert's Lodge

6057

3 bedroom, dog friendly self catering cottage near Yarmouth.


Surrounded by tranquil countryside on the edge of the Isle of Wight National Landscape and close to the charming seaside island towns of Yarmouth and Cowes, St Hubert's Lodge is a ...

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

7 nights from £1352

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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Bay Cottage is a 2 bedroom self catering cottage near the beach in Cowes.
  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £651 booking fees included

Bay Cottage

6150

2 bedroom self catering cottage near the beach in Cowes.


Tucked away in the charming village of Gurnard on the northwest coast of the Isle of Wight, this cosy two bedroom cottage offers a relaxed coastal lifestyle, complete with a pretty...

  • Sleeps 4 + cot
  • No pets
  • Changeover Fri

7 nights from £651

Little Field is a 3 bedroom, dog friendly holiday cottage near the beach near Ryde.
  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1109 booking fees included

Little Field

6123

3 bedroom, dog friendly holiday cottage near the beach near Ryde.


Tucked away on a quiet road, Little Field has been lovingly built by the owners and offers guests a peaceful and tranquil retreat with oodles of space and modern living. Situated o...

  • Sleeps 6 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £1109

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

7 nights from £1120 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 £1120

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 £721 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 £721

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 £929 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 £929

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

Choose from our exclusive collection at the best prices with real time availability.

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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 94 holiday cottages in South England available for your September break.