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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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    Merryweathers

    Hurst Green, Sussex

    0 0 reviews
    0 0 reviews
    Ref: M82561
    Wifi Car parking on site Rural Location
    21
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    Egmont Farm - Stag Lodge

    Northiam, near Rye, Sussex

    14/05/2019
    8.5 13 reviews
    8.5 13 reviews
    Ref: 30430
    Wifi Car parking on site Enclosed Garden / Patio Detached Garden / Patio Ground Floor Facilities Rural Location Woodburning Stove
    2
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    The Pod at Egmont
    2
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    Oakley Cottage

    Rye, Sussex

    0 0 reviews
    0 0 reviews
    Ref: M206366
    Coastal Wifi Woodburning Stove
    4
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    Wysteria Cottage

    Pembury, near Tunbridge Wells, Kent

    14/05/2019
    7.8 5 reviews
    7.8 5 reviews
    Ref: PKD
    Wifi Car parking on site Garden / Patio Open Fire
    4
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    The Camel House

    Benenden, near Cranbrook, Kent

    9 1 reviews
    9 1 reviews
    Ref: UKC3263
    Wifi Car parking on site Detached Garden / Patio Ground Floor Facilities Rural Location
    3
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    The Old Telephone Exchange

    Sissinghurst, Kent

    09/06/2019
    9.5 11 reviews
    9.5 11 reviews
    Ref: 26972
    Car parking on site Enclosed Garden / Patio Pub within 1 mile Pets go free Detached Garden / Patio Rural Location
    2
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    High Kiln

    Hastings, Sussex

    9.3 10 reviews
    9.3 10 reviews
    Ref: UKC355
    Coastal Hot Tub Wifi Car parking on site Enclosed Garden / Patio Pub within 1 mile Garden / Patio Sea View Rural Location
    4
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    Chessons Farm - Chessons Oast

    Wadhurst, near Tunbridge Wells, Sussex

    14/05/2019
    9 2 reviews
    9 2 reviews
    Ref: 8281
    Wifi Car parking on site Enclosed Garden / Patio Garden / Patio Ground Floor Facilities
    4
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    Chessons Farm - Stable Cottage
    4
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    The Old Vicarage

    Icklesham, near Rye, Sussex

    09/06/2019
    9.8 14 reviews
    9.8 14 reviews
    Ref: PUUE
    Coastal Luxury Wifi Car parking on site Pub within 1 mile Pets go free Garden / Patio Rural Location Open Fire
    12
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    The Old Library

    Broad Oak, near Heathfield, Sussex

    09/06/2019
    9.3 18 reviews
    9.3 18 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

    8.7 6 reviews
    8.7 6 reviews
    Ref: 19965
    Coastal Car parking on site Pub within 1 mile Garden / Patio Ground Floor Facilities Rural Location
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    Roadend Farm - The Wool Room Cottage
    6
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    Pipewell Cottage

    Winchelsea, Sussex

    23/05/2019
    8.5 8 reviews
    8.5 8 reviews
    Ref: 24664
    Coastal Enclosed Garden / Patio Pub within 1 mile Garden / Patio Rural Location
    6
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