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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 Berkley Lodges - The Lodge

    Beckley, near Rye, Sussex

    10 1 reviews
    10 1 reviews
    Ref: UK11986
    Wifi Car parking on site Garden / Patio Ground Floor Facilities Rural Location
    4
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    1
    1
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    The Shepherd’s Hut at Calvesfield Shaw

    Herstmonceux, near Hailsham, Sussex

    10 9 reviews
    10 9 reviews
    Ref: UK11682
    Coastal Wifi Car parking on site Garden / Patio Rural Location Woodburning Stove
    2
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    The Mission House

    Warninglid, Sussex

    10 2 reviews
    10 2 reviews
    Ref: M540086
    Luxury Wifi Car parking on site Ground Floor Facilities Rural Location Woodburning Stove Open Fire
    12
    5
    5
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    Newly listed
    10 1 reviews
    10 1 reviews
    Ref: M555015
    Luxury Wifi Car parking on site Pub within 1 mile Garden / Patio Rural Location
    4
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    Boreham Bridge Barn

    Ninfield, near Battle, Sussex

    10 1 reviews
    10 1 reviews
    Ref: UKC2756
    Car parking on site Detached Garden / Patio Ground Floor Facilities Rural Location
    6
    3
    2
    2
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    2 Stonedelph Cottage

    Warninglid, Sussex

    10 1 reviews
    10 1 reviews
    Ref: M521911
    Luxury Wifi Car parking on site Enclosed Garden / Patio Garden / Patio Rural Location Woodburning Stove
    5
    3
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    10 1 reviews
    10 1 reviews
    Ref: UK12154
    Wifi Car parking on site Garden / Patio
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    Freshwater Barn

    Benenden, Kent

    10 1 reviews
    10 1 reviews
    Ref: M37300
    Wifi Car parking on site Rural Location
    4
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    Mill Barn

    North Chailey, Sussex

    10 4 reviews
    10 4 reviews
    Ref: M493333
    Luxury Wifi Car parking on site Enclosed Garden / Patio Rural Location Woodburning Stove
    2
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    Birch Pavilion

    Tunbridge Wells, Sussex

    10 1 reviews
    10 1 reviews
    Ref: M53239
    Wifi Enclosed Garden / Patio Rural Location Open Fire
    15
    7
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    Horncombe Stables

    Ardingly, near Haywards Heath, Sussex

    10 5 reviews
    10 5 reviews
    Ref: UKC1725
    Wifi Car parking on site Enclosed Garden / Patio Pub within 1 mile Garden / Patio Rural Location
    5
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    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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