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 9 self catering cottages in High Weald to show you...
New bookings can be placed for any holiday arriving on or after the 1st March 2021. COVID-19
7 nights from £354
Hill Farm Cottage
45561 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 ...
7 nights from £354
7 nights from £490
Castlemans Stables West
44222 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...
7 nights from £490
Need more time? Reserve any cottage for up to 24 hours before booking.
24hr no commitment reservations
You can reserve your holiday dates on your favourite cottage for up to 24 hours. You might need to check with other guests in your party or simply consider whether this cottage is right for your holiday, either way we’re happy to give you the time to step away and mull over your options before paying a penny.
We’ll send you a reminder to see if you want it or not so you won’t lose out. Take time to think it over, you don’t have to rush your decision. Have a cup of tea and when you’re ready, hit the button to book your holiday and start looking forward to it.
7 nights from £490
Castlemans Stables East
44212 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...
7 nights from £490
7 nights from £578
The Annexe
45881 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...
7 nights from £578
7 nights from £392
Sawmill Cottage
44251 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 ...
7 nights from £392
7 nights from £347
Poppets Cottage
42801 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...
7 nights from £347
7 nights from £490
Medleys Barn
44762 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...
7 nights from £490
7 nights from £390
The Tea Hut
44771 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...
7 nights from £390
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
7 nights from £645
Woodpeckers Cottage
44731 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. ...
7 nights from £645
Show properties within 20 miles of High Weald