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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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  • Customers'
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    Malt Cottage

    Biddenden, Kent

    9.6 5 reviews
    9.6 5 reviews
    Ref: 24442
    Wifi Car parking on site Pub within 1 mile Detached Garden / Patio Ground Floor Facilities Rural Location
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    Castlemans Stables - Castlemans Stable East

    Sedlescombe, Sussex

    2019-05-21
    9.4 8 reviews
    9.4 8 reviews
    Ref: PPPS
    Wifi Car parking on site Pub within 1 mile Pets go free Garden / Patio Ground Floor Facilities Rural Location Woodburning Stove
    4
    2
    2
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    Castlemans Stables - Castlemans Stable West
    4
    2
    2
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    Chessons Farm - Chessons Oast

    Wadhurst, near Tunbridge Wells, Sussex

    14/05/2019
    9.3 8 reviews
    9.3 8 reviews
    Ref: 8281
    Wifi Car parking on site Enclosed Garden / Patio Garden / Patio Ground Floor Facilities
    4
    2
    1
    1
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    Chessons Farm - Stable Cottage
    4
    2
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    Castlemans Stables - Castlemans Stable West

    Sedlescombe, Sussex

    2019-05-21
    9.9 12 reviews
    9.9 12 reviews
    Ref: PPPR
    Wifi Car parking on site Pub within 1 mile Pets go free Garden / Patio Ground Floor Facilities Rural Location Woodburning Stove
    4
    2
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    2
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    Sawmill Cottage

    Tunbridge Wells, Kent

    9.2 12 reviews
    9.2 12 reviews
    Ref: PPPT
    Luxury Wifi Pub within 1 mile Pets go free
    2
    1
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    The Old Library

    Broad Oak, near Heathfield, Sussex

    2019-05-21
    9.6 16 reviews
    9.6 16 reviews
    Ref: W41686
    Car parking on site Pets go free Detached Garden / Patio Rural Location Woodburning Stove
    3
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    Roadend Farm - The Old Stable Cottage

    Rye, Sussex

    9.3 8 reviews
    9.3 8 reviews
    Ref: 19965
    Coastal Car parking on site Pub within 1 mile Garden / Patio Ground Floor Facilities Rural Location
    2
    1
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