Cottages For May in Sussex
Shhh! Don’t tell too many people this but, if you’re looking for a cottage holiday in May you might have stumbled on one of the best months to visit Sussex Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 27 self catering cottages available to rent in May in Sussex
7 nights from £741 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 £741
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20% off
11 Sep 2026 - 18 Sep 2026
From £919.00 £747.80 booking fees included
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20% off
18 Sep 2026 - 21 Sep 2026
£592.20 £486.36 booking fees included
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20% off
23 Sep 2026 - 26 Sep 2026
£570.50 £469.00 booking fees included
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20% off
2 Oct 2026 - 5 Oct 2026
£555.80 £457.24 booking fees included
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20% off
9 Oct 2026 - 16 Oct 2026
£746.00 £609.40 booking fees included
7 nights from £601 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 £601
Reserve your 2027 holiday for just £40.00
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7 nights from £816 * 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 £816 *
From £84 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 £84 per night
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7 nights from £959 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 £959
7 nights from £741 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 £741
7 nights from £1063 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 £1063
7 nights from £514 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 £514
From £66 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 £66 per night
Little Oak Farm
From £208 per night + £159 booking fees
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.
Spring is in full swing, it is often one of our sunniest months and some of the best local festivals start. And you get the pick of the properties in Sussex. So have a look through our 27 holiday cottages available this May in Sussex.
