East Sussex Cottages
With charming towns and villages, rolling countryside, gorgeous coast and fascinating history and heritage, a holiday in East Sussex has something for everyone. Explore the intriguing history of Battle and Hastings and enjoy the miles of rolling countryside for walks, including the magical Ashdown Forest. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 33 self catering cottages in East Sussex to show you...
From £80 per night + £63 booking fees
Bramley Lodge
61371 bedroom self catering cottage near Heathfield.
Soak up the scenic views of this enchanting lodge that sits within an orchard in the High Weald National Landscape. Its peaceful location is the perfect escape for a romantic getaw...
From £80 per night
7 nights from £656 booking fees included
Medleys Barn
44762 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...
7 nights from £656
Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.
Towels and readymade beds
All of our cottages provide bed linen and towels as standard, with a change of bedding included for holidays of two weeks or more. You’ll also find a fresh change of towels for each week (for in the house only, please bring your own for the beach) and tea towels a-plenty.
The beds will be readymade and waiting for you on arrival so you can simply sink into comfort and relax straight into your holiday.
Medleys Yard
7 nights from £1087.53 booking fees included
7 nights from £432 booking fees included
The Tea Hut
44771 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...
7 nights from £432
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £727 * booking fees included
Broyle Cottage
61743 bedroom, dog friendly self catering cottage near Hailsham.
Tucked away in a peaceful hamlet near the village of Herstmonceux, this quintessential English country cottage lends itself to family gatherings, celebrations or romantic breaks. B...
7 nights from £727 *
7 nights from £709 booking fees included
Nobby Nook
60061 bedroom, dog friendly self catering cottage near Battle.
This characterful gem, nestled in beautiful Sussex countryside, offers the perfect retreat for couples and solo travellers seeking a luxury escape. Nobby Nook is a lovingly conv...
7 nights from £709
7 nights from £537 booking fees included
Bloomsbury Cottage
61861 bedroom, dog friendly self catering cottage in Wadhurst.
For a digital detox head to the beautiful countryside of the High Weald National Landscape to stay at this unique timber-cladded barn that offers a peaceful escape just moments fro...
7 nights from £537
7 nights from £441 booking fees included
Carter's Cottage
60051 bedroom self catering cottage near Hailsham.
This cosy and well-appointed semi-detached country retreat sits on a working heavy horse farm, perfect for couples or solo travellers looking to unwind, reconnect and enjoy the slo...
7 nights from £441
7 nights from £525 booking fees included
Sawmill Cottage
44251 bedroom, dog-friendly self-catering cottage in Royal 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 £525
7 nights from £648 booking fees included
Moorhen Cottage
45481 bedroom, dog friendly self catering cottage near Battle.
Moorhen Cottage is a single-storey barn situated in a rural location in the heart of an organic dairy farm in the hamlet of Wartling with views of the Pevensey marshes and the Sout...
7 nights from £648
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!
Hastings Country Park has over 600 acres of countryside to discover along with lots of wildlife spotting to be done! There’s plenty of coast to discover, from the seaside towns of Eastbourne to Brighton, both lovely spots for a day out, or Camber Sands for watersports and catching waves.
The charming town of Lewes is certainly worth a visit for its photogenic medieval streets and olde worlde beauty and the idyllic Rye is a wonderful choice for a day trip, where you can wander around the cobbled streets, pay a visit to Camber Castle and head to a vineyard for award winning sparkling wine. And don't forget to head to Mayfield, a delightful village known as the place where Mary Poppins was written in the 1930s! There you will find independent shops, historic buildings and plenty of places for a delicious bite to eat.
From romantic retreats for the two of you to a family holiday home, find a self catering cottage in East Sussex here...
