Two night breaks in Sussex

A weekend away or two night short break in Sussex is so simple. No major preparations or need to pack up your life, just the perfect excuse to get away from it all for your favourite holiday cottage and slip under the radar of everyday life. With hand picked cottages across the south and west of the country there are endless places to escape to for a two night break with Classic Cottages. Take a look and see...

We have 5 holiday cottages available in Sussex for a two night break

We are no longer accepting new bookings for holidays arriving before the 4th June. COVID-19

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

7 nights from £372

1 bedroom, dog friendly self catering cottage in Buxted, East Sussex


Nestled in a peaceful setting and part of a former convent, Poppets Cottage is as charming as its name implies. Thoughtfully furnished in a country vintage style, this delightf...

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

7 nights from £372

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

7 nights from £510

3 bedroom, dog friendly self catering cottage in Chichester.


Nestled at the foot of the South Downs, in Chichester's Northern Quarter, this warm and welcoming townhouse is a simple walk to so much that this cosmopolitan and cultural haven ha...

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

7 nights from £510

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

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

7 nights from £525

2 bedroom, dog friendly self catering cottage near Battle.


In the heart of East Sussex's 1066 countryside and set within the High Weald Area of Outstanding Natural Beauty, Castlemans Stables East is a sympathetically converted stabled bloc...

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

7 nights from £525

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

7 nights from £525

2 bedroom, dog friendly self catering cottage near Battle.


Set within the High Weald Area of Outstanding Natural Beauty, in the heart of East Sussex's 1066 countryside, Castlemans Stables West is a sympathetically converted stable block, w...

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

7 nights from £525

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £531

2 bedroom, dog friendly self catering cottage in Burwash.


The Stable Block is situated in the grounds of the owner's Georgian home on the edge of the village of Burwash. It has two double bedrooms with en suites and a beautiful large open...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £531