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 7 holiday cottages available in Sussex for a two night break

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

7 nights from £416

The Tea Hut

4477

1 bedroom, dog-friendly self-catering cottage near Crowborough.


The Tea Hut is situated up a private drive in High Hurstwood. Nestled in the picturesque Sussex countryside it is a great base from which to explore Ashdown Forest and the local to...

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

7 nights from £416

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

7 nights from £511

Castlemans Stables East

4421

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 stable block...

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

7 nights from £511

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

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

7 nights from £511

Castlemans Stables West

4422

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 £511

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £546

Gunbanks Forge

4703

2 bedroom self catering apartment near Heathfield.


Gunbanks Forge is a peaceful retreat in the High Weald Area of Outstanding Natural Beauty, a short drive to the Sussex coast. As you enter through the wooden door of this beauti...

  • Sleeps 4
  • Regret no pets
  • Changeover Fri

7 nights from £546

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

7 nights from £600

Medleys Barn

4476

2 bedroom, dog-friendly self-catering cottage near Crowborough.


Medleys Barn in High Hurstwood is an ideal base for exploring Ashdown Forest or for visits to Glyndebourne. Once a cart barn on a well-established fruit farm, this charming barn co...

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

7 nights from £600

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £872

Danny Cottage

4458

3 bedroom thatched, dog-friendly self-catering cottage in Alfriston.


Danny Cottage is a beautiful Grade II Listed, 16th Century timber-framed thatched cottage situated in a rural position on the edge of Alfriston village. Purchased from the National...

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £872

Medleys Yard

  • Sleeps 6 + 3 cots in 2 properties
  • Changeover Fri

7 nights from £1016