Short breaks in Sussex
Sussex is a wonderful choice for blissful weekend escapes spent discovering culture and history, exploring ancient woodlands and glorious coastline, award-winning vineyards, and wandering around the pretty towns and villages. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 40 self-catering cottages in Sussex available for a Short Break
7 nights from £557
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 £557
7 nights from £653 *
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 £653 *
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20% off
27 Dec 2025 - 3 Jan 2026
£1305.00 £1044.00
7 nights from £1222
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 £1222
7 nights from £378
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 £378
Little Oak Farm
7 nights from £254
From £85 per night
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...
From £85 per night
7 nights from £598
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 £598
7 nights from £659
Strawberry Hole Barn
58142 bedroom thatched, dog friendly self catering cottage near Rye.
Escape to this gorgeous thatched barn, sat in the grounds of the owners' double oast house, within walking distance of Great Dixter House and Gardens. This spacious property offers...
7 nights from £659
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7 nights from £474
Pump Cottage
57882 bedroom self-catering cottage in Rye.
Situated in the heart of Rye and just a short walk from the railway station, Pump Cottage is perfectly positioned for exploring this medieval town, 1066 country and the golden beac...
7 nights from £474
7 nights from £585 *
The Laundry
56502 bedroom, dog friendly self catering cottage near Polegate.
This retro-style retreat is the perfect place to relax, recharge and reconnect. It sits in the picturesque downland village of Jevington within the South Downs National Park, just ...
7 nights from £585 *
Just a short journey from London, whisk yourself away for a relaxing break in Sussex anytime of the year. There's so many fantastic locations to choose from, including the timeless town of Rye and Battle and the peace and serenity of the South Downs, to name just a few. Whether you're looking for a romantic escape just for the two of you, or you're bringing the whole family along, find your perfect holiday cottage in Sussex for an unforgettable weekend away...