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
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 152 luxury self catering cottages in South England
7 nights from £620 booking fees included
The Old Tractor Shed
61802 bedroom, dog friendly self catering cottage near Winchelsea.
Tucked away on a working sheep farm close to the coast and the medieval towns of Rye and Winchelsea, this peaceful escape is surrounded by beautiful farmland and scenic footpaths i...
7 nights from £620
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
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 £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 £1521 booking fees included
St Hubert's Lodge
60573 bedroom, dog friendly self catering cottage near Yarmouth.
Surrounded by tranquil countryside on the edge of the Isle of Wight National Landscape and close to the charming seaside island towns of Yarmouth and Cowes, St Hubert's Lodge is a ...
7 nights from £1521
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £853 * booking fees included
Grey Gulls
61594 bedroom dog friendly self catering cottage with sea views in Seaview.
This beautifully presented, semi-detached, three-storey townhouse is set in the sought-after village of Seaview, just a stone's throw away from stunning beaches with crystal clear ...
7 nights from £853 *
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 £513 booking fees included
Bay Cottage
61502 bedroom self catering cottage near the beach in Cowes.
Tucked away in the charming village of Gurnard on the northwest coast of the Isle of Wight, this cosy two bedroom cottage offers a relaxed coastal lifestyle, complete with a pretty...
7 nights from £513
7 nights from £850 booking fees included
Wickings
61013 bedroom, dog friendly holiday cottage near the beach in Ventnor.
Nestled in the sheltered seaside town of Ventnor, blessed with its own gentle microclimate, this wonderfully welcoming and peaceful retreat is perfect for relaxing, unwinding and s...
7 nights from £850
7 nights from £818 * booking fees included
Little Field
61233 bedroom, dog friendly holiday cottage near the beach near Ryde.
Tucked away on a quiet road, Little Field has been lovingly built by the owners and offers guests a peaceful and tranquil retreat with oodles of space and modern living. Situated o...
7 nights from £818 *
7 nights from £1136 booking fees included
Dunks Cottage
60744 bedroom, dog friendly self catering cottage near Cranbrook.
Overlooking the village green of Sandhurst, Kent, in the beautiful High Weald National Landscape (Area of Outstanding Natural Beauty), this wonderfully spacious, semi-detached cott...
7 nights from £1136
We are Gold accredited with the Green Tourism Business Scheme.
Green Tourism Business Scheme
As a company, we look across our business and try to make sustainable changes and decisions. From using recycled paper in our printers to putting in measures for using less energy in our offices, we keep an eye on our impact on the environment.
Beyond our offices, we have passed on the same ethics to our holiday cottage owners by setting up our own Green Scheme that they can join. Each property has to tick off a certain number of actions to be included in the scheme, many of which go above and beyond the GTBS requirements.
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.
