Family friendly holiday cottages in Sussex
Have your own space to be able to do things when you want in a family friendly, self catering holiday cottage in Sussex. The best family holidays leave little ones with memories for years to come, so book your ideal place to stay for a UK holiday with the kids.
Our exclusive ferry discounts of up to 25% will make your island trip with Classic plain sailing.We have 26 self catering cottages for a family holiday in Sussex to show you.
7 nights from £432 booking fees included
The Tea Hut
44771 bedroom, dog-friendly self-catering cottage near Crowborough and the Ashdown Forest.
The Tea Hut is situated up a private drive in High Hurstwood. Nestled in the picturesque Sussex countryside it is a great base from which to explore Ashdown Forest and the local to...
7 nights from £432
From £57 per night + £53 booking fees
Douglas Fir
5290Dog friendly shepherds hut near Pulborough.
Hidden away in the West Sussex countryside yet just two hours from London, this luxury shepherd's hut offers a magical escape for two. Beautiful and handcrafted, it has all you ...
From £57 per night
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
7 nights from £537 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 £537
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7 nights from £563 booking fees included
Hayesland Lodge
57001 bedroom, dog friendly self catering cottage near Rye.
This gem is situated in a peaceful and tranquil setting in a National Landscape (an Area of Outstanding Natural Beauty) with farmland views, a short drive from the coast and the me...
7 nights from £563
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
7 nights from £656 booking fees included
Medleys Barn
44762 bedroom, dog-friendly self-catering cottage near Crowborough and the Ashdown Forest.
Medleys Barn in High Hurstwood is an ideal base for exploring Ashdown Forest or for visits to Glyndebourne. Once a cart barn on a well-established fruit farm, this charming barn co...
7 nights from £656
7 nights from £709 booking fees included
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 £709
7 nights from £504 booking fees included
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 £504
7 nights from £543 booking fees included
Reysons Barn
52852 bedroom thatched self catering cottage near Rye.
Reysons Barn is perfect for couples and families who are looking for a rural escape in East Sussex. Converted in 2009, this lovely thatched barn sits on the edge of a small orchard...
7 nights from £543
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Whether you are escaping for the first time with your newborn or holidaying with the whole tribe, it is great to have your own space and to be able to do things when you want. Family holidays can seem stressful but we've thought of everything so when you arrive in your family holiday destination, you can put your feet up and just relax. Your family's cottage holiday starts here.
[Region] brings a wealth of opportunities for families of all ages; being away with the kids can be filled with exciting days out exploring new places, or more sedate members of the family needn't leave the luxury of the holiday cottage. There's even room for four-legged members of the family to make sure no-one is left out of what has the potential to be the best family holiday yet.
UK breaks for families can cater for all requirements; crazy adrenalin-fuelled action or chilled-out respites, summers by the sea or adventures out in the countryside. Family holidays in Sussex have all the above and more. The hard part is choosing which of our 26 family cottages in Sussex you want to stay in the most!