Cottages in Sussex for the Summer Holidays

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. 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.Read more

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. 

Isle of Wight Ferry Booking Our exclusive ferry discounts will make your island trip with Classic plain sailing.

Choose from 32 school summer holiday cottages in Sussex

The Coach House is a 2 bedroom, dog friendly self catering cottage near Battle.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £959

The Coach House

4735

2 bedroom, dog friendly self catering cottage near Battle.


For a rural experience stay at The Coach House, the perfect getaway for families and friends in this peaceful part of Sussex. As you step inside the stable-door you are welcomed...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £959

Thornden Farm Holiday Cottages

  • Sleeps 12 + 4 cots in 4 properties
  • Changeover Sat

7 nights from £3216

The Old Stable is a 1 bedroom, dog friendly self catering cottage near Battle.
  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £692

The Old Stable

4733

1 bedroom, dog friendly self catering cottage near Battle.


Enjoy precious time together at The Old Stable, a wonderful cottage for couples looking for a quiet getaway in this peaceful part of Sussex. As you step inside the stable-door y...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £692

The Old Barn is a 2 bedroom, dog friendly self catering cottage near Battle.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £903

The Old Barn

4734

2 bedroom, dog friendly self catering cottage near Battle.


The Old Barn is a wonderful hideaway, perfect for families looking for a true rural experience in this beautiful and peaceful part of East Sussex. As you open the stable-door to...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Sat

7 nights from £903

The Byre is a 1 bedroom self catering cottage near Battle.
  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £662

The Byre

4732

1 bedroom self catering cottage near Battle.


Bursting with character and charm, The Byre is waiting to give you that rural experience. Situated in 12 acres of 1066 countryside it is one of Thornden Farm's original outbuilding...

  • Sleeps 2 + cot
  • No pets
  • Changeover Sat

7 nights from £662

Hill Farm Cottage is a 1 bedroom self-catering cottage near Battle.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £762

Hill Farm Cottage

4556

1 bedroom self-catering cottage near Battle.


Situated in the High Weald National Landscape within easy reach of the coast, this beautifully crafted Sussex barn is the perfect retreat for couples looking for a relaxing break i...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £762

We’re a Visit England Quality Accredited Agency for our high standards in holiday letting.

Medleys Yard

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

7 nights from £1071

Medleys Barn is a 2 bedroom, dog-friendly self-catering cottage near Crowborough and the Ashdown Forest.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £990

Medleys Barn

4476

2 bedroom, dog-friendly self-catering cottage near Crowborough and the Ashdown Forest.


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 £990

The Tea Hut is a 1 bedroom, dog-friendly self-catering cottage near Crowborough and the Ashdown Forest.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

From £81 per night

The Tea Hut

4477

1 bedroom, dog-friendly self-catering cottage near Crowborough and the Ashdown Forest.


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

From £81 per night

Castlemans Stables East is a 2 bedroom, dog-friendly self-catering cottage near Battle.
  • Sleeps 4 + 2 cots
  • Dogs welcome
  • Changeover Fri

7 nights from £844

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 one of a pair of sympathetically convert...

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

7 nights from £844

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