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High Weald

The High Weald just 30 miles south of London is one of the best surviving medieval landscapes in Northern Europe. With a backdrop of wooded rolling hills, sandstone outcrops, a patchwork of fields and ancient routes it is a fabulous area to go on a self-catering holiday. The whole area includes part of Kent and Sussex right in the heart of South East England, with over 900 square miles to explore.

There is a great selection of holiday cottages in High Weald and by using our extensive feature list you can easily find your perfect one such as enclosed garden if taking children or dogs, a village or pub within walking distance, or part of our luxury collection, the choice really is yours.

The region is perfect for outdoor enthusiasts with an amazing network of footpaths, bridleways and byways as well as lots of nature reserves. There are mysterious woodlands, sunken lanes created by the Saxons and Tudors, lovely timber framed buildings and the legendary Ashdown Forest to explore. There is something for everyone from nature lovers, families with young children to avid ramblers.

The area has a fascinating past and its towns and villages are lovely places to explore. Many aristocratic families have left beautiful manor houses now open to the public such as Penshurst Place & Gardens and Sissinghurst Castle & Gardens. Try to fit in some of the impressive castles, Hever Castle is lovely for a day out and you’ll love exploring the extensive grounds.

Ardingly is home to the famous boys public school, Ardingley College, and also has a pretty high street. Battle, built on the site of the battle of 1066, where William the Conqueror defeated King Harold, is now a bustling market town and boasts Battle Abbey.

Choose from self-guided circular walks or for the more adventurous the High Weald Landscape Trail, a 95 mile route going from east to west. All the time you will come across Michelin starred restaurants and gastro country pubs in pretty villages, there is plenty to keep you entertained and have a great holiday in your cottage rental in High Weald.

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    The Tea Hut

    Crowborough, Sussex

    10 1 reviews
    10 1 reviews
    Ref: M511784
    Wifi Car parking on site Rural Location Woodburning Stove
    2
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    Pickdick Stable

    Brede, near Rye, Sussex

    10 24 reviews
    10 24 reviews
    Ref: UKC1367
    Luxury Wifi Car parking on site Detached Rural Location
    2
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    Newly listed

    Woodpeckers

    Cowbeech, near Hailsham, Sussex

    10 1 reviews
    10 1 reviews
    Ref: UK11388
    Car parking on site Enclosed Garden / Patio Pub within 1 mile Pets go free Garden / Patio Ground Floor Facilities Rural Location
    4
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    Newly listed
    10 1 reviews
    10 1 reviews
    Ref: M555017
    Luxury Wifi Car parking on site Pub within 1 mile Garden / Patio Rural Location
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    Castlemans Stables West

    Sedlescombe, near Battle, Sussex

    10 1 reviews
    10 1 reviews
    Ref: M375474
    Wifi Car parking on site Enclosed Garden / Patio Rural Location Woodburning Stove Baby and Toddler Friendly
    4
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    Castlemans Stables East
    4
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    Point Cottage

    Ticehurst, near Tunbridge Wells, Sussex

    10 1 reviews
    10 1 reviews
    Ref: UKC2506
    Wifi Car parking on site Enclosed Garden / Patio Pub within 1 mile Pets go free Detached Garden / Patio Rural Location Open Fire
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    Gulls Way

    Rye, Sussex

    10 1 reviews
    10 1 reviews
    Ref: M414352
    Wifi Woodburning Stove Open Fire
    7
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    Garden Cottage

    Icklesham, Sussex

    10 1 reviews
    10 1 reviews
    Ref: M76144
    Wifi Car parking on site Rural Location Woodburning Stove
    3
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    Masketts Barn

    Nutley, Sussex

    10 1 reviews
    10 1 reviews
    Ref: M398660
    Luxury Wifi Car parking on site Rural Location Woodburning Stove Open Fire
    9
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    The Shepherd’s Hut at Calvesfield Shaw

    Herstmonceux, near Hailsham, Sussex

    10 3 reviews
    10 3 reviews
    Ref: UK11682
    Coastal Wifi Car parking on site Pets go free Garden / Patio Rural Location Woodburning Stove
    2
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    Newly listed
    10 1 reviews
    10 1 reviews
    Ref: M555016
    Luxury Wifi Car parking on site Pub within 1 mile Garden / Patio Rural Location
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    Spilstead Barn

    Sedlescombe, Sussex

    10 1 reviews
    10 1 reviews
    Ref: M539655
    Luxury Wifi Car parking on site Enclosed Garden / Patio Pub within 1 mile Garden / Patio Rural Location
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