Cottages in Sussex for the Summer Holidays

Just a hop, skip and a jump from London, Sussex is a great choice for a summer getaway without having to travel too far. Read more

Head to the countryside to stay in a luxury self catering cottage in Sussex for your summer holiday. Take advantage of those long summer days, wander through woodlands and nature reserves and explore the dreamy English countryside.

Summer Holiday Cottages in Sussex

At Classic Cottages we understand how important your accommodation is in making or breaking your holiday experience. That's why we handpick all of our properties, personally inspecting each one so that exacting standards are met. From start to finish we want your holiday to be as easy and relaxed as possible, and will provide you with help and support every step of the way. All you need to do? Pick your favourite cottage and embrace the holiday of a lifetime in Sussex. 

Choose from 8 school summer holiday cottages in Sussex

  • Sleeps 5 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1128

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 £1128

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

7 nights from £525

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 £525

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

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £750

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 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £750

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £696

Woodpeckers Cottage

4473

1 bedroom self catering cottage near East Grinstead.


Woodpeckers is a luxury boutique-style holiday cottage perfect for couples wanting to relax in the Sussex countryside with access to country walks and near to Ashdown Forest. Th...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £696

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

7 nights from £765

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 £765

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

7 nights from £765

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 stabled bloc...

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

7 nights from £765

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

7 nights from £548

Poppets Cottage

4280

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 £548

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

7 nights from £865

3 Little London Mews

4361

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 £865

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.