Holiday cottages for September in Sussex
If Septembers past are anything to go by, this is often one of the loveliest months to enjoy a holiday cottage in Sussex.Read more
The beaches are still peachy, the sea's had all summer to warm up and the schools have gone back. So you can have more sand, more cliffs and more moor to yourself. Use the search options on the left to choose your holiday dates. We've got 33 holiday cottages in Sussex available for your September break.
We have 33 Sussex holiday cottages available in September.
7 nights from £735
Heringaud Barn
52512 bedroom, dog friendly self catering cottage near Alfriston.
This peaceful retreat is situated in the sleepy picturesque village of West Dean in the heart of the South Downs National Park, a short distance from Cuckmere Haven and the Seven S...
7 nights from £735
From £133 per night
Little Oak Treehouse
5288Gorgeous dog friendly treehouse with a wood burner near Pulborough.
This gorgeous quirky treehouse situated just two hours from London, is the perfect escape for a romantic getaway. Truly unique and in a lovely part of West Sussex, it sits in a sec...
From £133 per night
From £92 per night
Cala Lily
5289Dog friendly shepherds hut near Pulborough.
With countryside views and just two hours from London, Cala Lily is a luxury shepherd's hut situated in the beautiful countryside of West Sussex and offers a dreamy escape where yo...
From £92 per night
From £92 per night
Douglas Fir
5290Dog friendly shepherds hut near Pulborough.
Hidden away in the West Sussex countryside yet just two hours from London, this luxury shepherd's hut offers a magical escape for two. Beautiful and handcrafted, it has all you ...
From £92 per night
We’ve been raising the standards of self catering holidays since 1977.
Our family ethos
Tony and Clare Tregoning started the business back in 1977 and their dedication to quality and excellence is at the heart of everything we do. Tony is sadly no longer with us, but we still adhere to their original ethos of finding holiday homes we would like to stay in and have slowly grown the company to find the best picks of properties across the counties. Plus Clare still drops in to keep us on our toes.
As an independent, family-run company, we wouldn’t expect you to stay anywhere we wouldn’t want to stay ourselves. And we’re pretty picky. We want you to walk into your handpicked holiday home and say ‘wow’, sit back and relax.
From £83 per night
Jessie
5231Luxury dog friendly Shepherds Hut near Battle.
Jessie is a gorgeous shepherd's hut situated two hours from London, tucked away down a long meandering path in a paddock between crab apple and cherry trees, with views of the Suss...
From £83 per night
7 nights from £1332
South Barn at Pickeridge
52113 bedroom, dog friendly self catering cottage near Haywards Heath.
South Barn at Pickeridge is tucked away on a 120 acre working farm in a secluded valley between West Hoathly and Ardingly. It's the perfect retreat for families and friends looking...
7 nights from £1332
7 nights from £1395
Apsley Cottage
51483 bedroom, dog friendly self catering cottage near Midhurst
Apsley Cottage is a welcoming cottage with a hot tub on the Cowdray Estate, situated in a secluded location just outside the picturesque village of Bepton, a short drive from Midhu...
7 nights from £1395
7 nights from £3200
Challens Yarde
51494 bedroom, dog friendly self catering cottage with hot tub near Midhurst
Challens Yarde is a Grade II Listed luxury holiday cottage with hot tub on the Cowdray Estate and can be found on a picturesque rural lane in the village of Easebourne, perfect for...
7 nights from £3200
7 nights from £825
The Granary
50372 bedroom, dog friendly self catering cottage near Haywards Heath.
The Granary is situated beside a working organic farm, a short walk from the picturesque village of Cuckfield on the edge of the High Weald, an Area of Outstanding Natural Beauty (...
7 nights from £825
7 nights from £1188
The Piggery at John Bulls House
49221 bedroom self catering cottage near Horsham.
The Piggery at John Bulls House is the perfect retreat for couples looking to stay at the foot of South Downs National Park. Situated in a quiet, rural and secluded location it giv...
7 nights from £1188
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!
