High Weald Cottages

Covering parts of Kent, Sussex and Surrey, High Weald is a designated Area of Outstanding Natural Beauty known for its rolling countryside and gorgeous landscapes. With plenty of opportunities for walking and taking advantage of the great outdoors, High Weald is a wonderful place to spend a holiday if you’re after fresh air and a rural retreat.Read more

Full of adventures, take your pick of the many outdoor activities from walking, rock climbing, cycling and wildlife watching. Explore the varied landscape with its woodland, parks and hills and venture to the nearby town of Royal Tunbridge Wells for shopping and a selection of delicious restaurants. Explore Ashdown Forest to discover Pooh Woods and stay nearby in Buxted and Mayfield to make the most of everything the High Weald area has to offer.

We have 10 self catering cottages in High Weald to show you...

New bookings can be placed for any holiday arriving on or after the 12th April for cottages in England and we are accepting Easter bookings at our properties in Wales, for those that can legally travel. COVID-19

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £354

Hill Farm Cottage

4556

1 bedroom self-catering cottage near Battle.


Situated in the High Weald Area of Outstanding Natural Beauty within easy reach of the coast, this beautifully crafted Sussex barn is the perfect retreat for couples looking for a ...

  • Sleeps 2 + cot
  • Regret no pets
  • Changeover Fri

7 nights from £354

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

7 nights from £490

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 £490

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

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

7 nights from £490

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 £490

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £578

The Annexe

4588

1 bedroom self-catering cottage in Mayfield.


The Annexe can be found at the end of a private road, secluded yet within walking distance of the beautiful historic village of Mayfield. Presented to a lovely standard, The Ann...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £578

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £392

Sawmill Cottage

4425

1 bedroom, dog-friendly self-catering cottage in Tunbridge Wells.


On the site of the 18th Century sawmill and on the common across the road from The Pantiles, Sawmill Cottage is ideally suited for couples wishing to explore the Royal Spa town of ...

  • Sleeps 2 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £392

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

7 nights from £347

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 £347

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

7 nights from £490

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 £490

Medleys Yard

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

7 nights from £880

Arrive at your handpicked holiday home safe in the knowledge it’s been fully inspected.

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

7 nights from £390

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 £390

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £645

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 easy access to country walks and nearby Ashdown Forest. ...

  • Sleeps 2
  • Regret no pets
  • Changeover Fri

7 nights from £645

Show properties within 20 miles of High Weald