May half term holiday cottages
With a cool breeze and the hint of summer on its way, May is a wonderful time of year to discover a beautiful corner of the UK. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We've got 27 holiday cottages matching your search in Sussex...
7 nights from £757 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 £757
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30% off
21 Aug 2026 - 28 Aug 2026
From £1020.00 £732.90 booking fees included
7 nights from £678 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 £678
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.
7 nights from £1078 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 £1078
From £85 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 £85 per night
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £989 booking fees included
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 £989
7 nights from £757 booking fees included
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 £757
7 nights from £1087 booking fees included
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 £1087
7 nights from £517 booking fees included
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 £517
Little Oak Farm
From £218 per night + £159 booking fees
From £69 per night + £53 booking fees
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 £69 per night
Our property managers are local experts who handpick perfect places to stay.
Local experts
We scour the coast and country to winkle out bits worth sharing with you, the best properties in lovely locations. While we’re out and about, we gather together the best things to do so that you can start planning your holiday as soon as you’ve booked.
The ‘Explore Nearby’ tab on our cottage pages show what’s nearby along with relevant articles from our holiday guides from Notes and Stories, where you’ll find hand-written experiences of outings across the South and West, from dog-friendly pubs on the Isle of Wight to free things to do in south Devon and everything in between.
With the summer holidays still out of reach and warmer weather on its way, why not take advantage of this lovely time of year and escape to Sussex. Travel solo, have a romantic getaway, or take advantage of some true family time and have a half term to remember in a cottage this half term, get ready to make memories you’ll keep forever.
