Cottages in South England
Whether you want to escape the mainland in a coastal cottage on the Isle of Wight or you long for idyllic days spent milling around the rolling hills of Sussex, we’ve got a holiday cottage in the South of England for you.
Home to the Garden of England (more commonly known as Kent), alongside the coastal wiles of Sussex, Hampshire, Essex, and the Isle of Wight, the South of England is a grand destination indeed for a memorable holiday. Read more
A catalogue of intriguing historical buildings (including the impressive Windsor Castle and Canterbury Cathedral) and captivating landmarks make for some truly fascinating days out – not to mention the countless opportunities for watersports at one of the many beautiful beaches along the south coast. Leave the mainland behind for a self catering holiday on the Isle of Wight where you’ll find sweeping coastlines punctuated with white cliffs and gardens aplenty – as well as some truly unmissable festivals. Get lost in the enthralling history of 1066 country, sit down for a lavish afternoon tea, or spend your time in Sussex enjoying the results of a British vineyard – when in Rome! One of the best things about these southern beauties is their close proximity to London, meaning you’re never far from a weekend away or a day trip to the beach.
We have 186 luxury self catering cottages in South England
Bagwich House
7 nights from £1560
7 nights from £552
Blakesley Cottage
55652 bedroom, dog friendly self catering cottage in Godshill, Isle of Wight.
Nestled in the very heart of the Isle of Wight's rolling countryside close to the quintessential English village of Godshill yet just a short drive away from the stunning beaches o...
7 nights from £552
7 nights from £1932
Tamarisk House
55164 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
If you are seeking the ultimate coastal getaway with more than a little exclusivity, look no further than this luxurious retreat in Seaview overlooking the beautiful Solent on the ...
7 nights from £1932
7 nights from £1444 *
Halland Rise
55004 bedroom, dog friendly holiday cottage with sea views in Seaview, Isle of Wight.
Introducing, Halland Rise, a stunning detached house sleeping eight guests, nestled in Seaview, one of the Island's most sought-after villages. With a choice of hidden coves and lo...
7 nights from £1444 *
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.
7 nights from £1374
Firestone Lodge
54944 bedroom, dog friendly holiday cottage near the beach near Ryde, Isle of Wight.
Set back from the road and only a short walk from the pretty tidal estuary at Wootton Creek, Firestone Lodge sets the scene for your luxury holiday with family, friends and your mu...
7 nights from £1374
7 nights from £1450
Costers Lodge
54903 bedroom, dog friendly self catering cottage in Midhurst.
Sitting in gorgeous countryside, this 100 year old luxury sandstone cottage is just a stone's throw from Cowdray House and only a five-minute drive from the centre of Midhurst. It'...
7 nights from £1450
7 nights from £1788
Tap Cottage
54173 bedroom, dog friendly self catering cottage near Romsey
Within the bustling village of Stockbridge, this contemporary cottage has been renovated to an exceptional standard. There is so much to explore locally; with sites such as Salisbu...
7 nights from £1788
7 nights from £1538
Dar View
54584 bedroom self catering cottage near the beach in Bembridge, Isle of Wight.
If you are looking for a stylish, spacious, yet comfortable retreat which boasts a superbly sought-after location, welcome to Dar View. An exquisite 'New England' style holiday...
7 nights from £1538
7 nights from £660
Lower Buoys
54572 bedroom self catering apartment near the beach in Seaview, Isle of Wight.
Looking for buried treasure and an Island adventure? Look no further than this super ground floor, luxuxy apartment in a premier destination in the heart of Seaview. Enjoy beachsid...
7 nights from £660
7 nights from £549
North Barn at Pickeridge
52152 bedroom self catering cottage near Haywards Heath.
North Barn at Pickeridge is the perfect abode for couples and families. It sits in a secluded location on a 120 acre working farm in a beautiful valley between Ardingly and West Ho...
7 nights from £549
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!