Holiday cottages for 2027 in Sussex
Ready to start planning your 2027 adventure? Choose from a growing collection of holiday cottages across the UK. Plus, you can now reserve your 2027 holiday for just £40, with no need to pay the remaining deposit until 1st November. Read more
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.Self catering holiday cottages for rent in 2027
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
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20% off
8 Sep 2026 - 11 Sep 2026
From £630.70 £517.16 booking fees included
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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 £538 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 £538
Reserve your 2027 holiday for just £40.00
Find out more
7 nights from £728 * 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 £728 *
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
British Travel Awards 2025
Best company for UK holiday home rentals
7 nights from £732 * 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 £732 *
7 nights from £620 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 £620
7 nights from £789 * 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 £789 *
7 nights from £442 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 £442
Little Oak Farm
From £179 per night + £159 booking fees
From £57 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 £57 per night
We’re here to help you find your perfect place to stay 7 days a week.
Open 7 days a week
Call our office on 01326 555555, email hello@classic.co.uk or click on the live chat button in the bottom right of the screen to talk directly to someone who can help with choosing your holiday. If you have any questions or need a hand with the booking process, we’re happy to help.
After booking your holiday with us, you’ll receive your holiday details two weeks before your holiday. This also includes our emergency out of hours phone number for when the office is closed, so we’re never more than a phone call away!
Long, leisurely countryside walks, exploring somewhere new, the warm sand between your toes, finding sun-soaked spots for lazy afternoon picnics and taking the time to enjoy those special sunrises and sunsets. Sound good? Whether you're looking for a coastal holiday or a rural retreat, or a cottage with a hot tub or swimming pool, we have a portfolio of properties ready and waiting for you to start planning your next self catering holiday in Sussex.
