Cottages in Sussex for the Summer Holidays
Just a hop, skip and a jump from London, Sussex is a great choice for a summer getaway without having to travel too far. Head to the countryside to stay in a luxury self catering cottage in Sussex for your summer holiday. Take advantage of those long summer days, wander through woodlands and nature reserves and explore the dreamy English countryside. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.Choose from 35 school summer holiday cottages in Sussex
7 nights from £1566
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 £1566
7 nights from £730
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 £730
7 nights from £1090
Austin House
60193 bedroom self catering cottage near the beach in Worthing.
Situated in the heart of Worthing, just a short walk from the seafront with its long promenade and Victorian pier, this spacious house is perfect for family get-togethers and those...
7 nights from £1090
7 nights from £851
Pomona Annexe
60532 bedroom, dog friendly self catering cottage in Battle.
Located just a short drive from the stunning Sussex coast and a short ten-minute walk to the RSPB Fore Wood Nature Reserve and the iconic town of Battle, Pomona Annexe is a charmin...
7 nights from £851
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15% off
3 Apr 2026 - 10 Apr 2026
From £672.00 £571.20
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £1175
Rockfield Lodge
60543 bedroom, dog friendly self catering cottage near Battle.
Situated in beautiful grounds just outside the medieval town of Battle and a short drive from Hastings and St Leonards-on-Sea, this delightful lodge offers a spacious holiday abode...
7 nights from £1175
7 nights from £2193
Ellenhall
59904 bedroom, dog friendly self catering cottage near Battle.
Escape to this picture-perfect countryside retreat which sits in a salubrious location in the High Weald National Landscape (Area of Outstanding Natural Beauty). Surrounded by anci...
7 nights from £2193
7 nights from £542
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 £542
7 nights from £651
Isla Rose
5948Dog friendly shepherds hut near Pulborough.
This oh-so-romantic shepherd's hut for two lies in the beautiful countryside of West Sussex and offers an idyllic, peaceful escape that's dog friendly too. Just a mere two hours...
7 nights from £651
Little Oak Farm
7 nights from £1953
7 nights from £931
Mellifount Farm
58392 bedroom self catering cottage near Haywards Heath.
Escape to the Sussex countryside and stay in this beautiful oak-framed barn situated in a quiet rural location overlooking wooded farmland and paddocks, where you can sometimes see...
7 nights from £931
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.
Summer Holiday Cottages in Sussex
At Classic Cottages we understand how important your accommodation is in making or breaking your holiday experience. That's why we handpick all of our properties, personally inspecting each one so that exacting standards are met. From start to finish we want your holiday to be as easy and relaxed as possible, and will provide you with help and support every step of the way. All you need to do? Pick your favourite cottage and embrace the holiday of a lifetime in Sussex.
