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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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    Water’s Edge

    Rolvenden Layne, near Tenterden, Kent

    8.9 11 reviews
    8.9 11 reviews
    Ref: PNNO
    Car parking on site Pub within 1 mile Detached Garden / Patio Rural Location
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    Sunnymead Cottages - Russets

    High Hurstwood, near Uckfield, Sussex

    14/05/2019
    9.4 10 reviews
    9.4 10 reviews
    Ref: PGZ
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    Sunnymead Cottages - Pippins
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    Lanterns

    Udimore, Rye, Sussex

    23/05/2019
    8.2 13 reviews
    8.2 13 reviews
    Ref: E4911
    Coastal Wifi Car parking on site Enclosed Garden / Patio Pub within 1 mile Detached Garden / Patio Rural Location
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    Brailsham Barn Holiday Cottages - Windmill Cottage

    Heathfield, near Broad Oak, Sussex

    23/05/2019
    9.7 9 reviews
    9.7 9 reviews
    Ref: 28698
    Car parking on site Pub within 1 mile Garden / Patio Ground Floor Facilities Rural Location
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    Brailsham Barn Holiday Cottages - Orchard Cottage
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    Lower Marley Farm - Quince Cottage

    Sedlescombe, near Battle, Sussex

    09/06/2019
    8.6 14 reviews
    8.6 14 reviews
    Ref: 27443
    Coastal Wifi Car parking on site Enclosed Garden / Patio Pub within 1 mile Pets go free Garden / Patio Rural Location
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    Lower Marley Farm - Apple Cottage
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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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    Windmill Barn

    Windmill Hill, near Hailsham, Sussex

    09/06/2019
    9.9 30 reviews
    9.9 30 reviews
    Ref: UKC2485
    Luxury Wifi Car parking on site Pub within 1 mile Detached Garden / Patio Woodburning Stove
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    Snaylham House Cottage

    Icklesham, Winchelsea, Sussex

    23/05/2019
    9.2 11 reviews
    9.2 11 reviews
    Ref: PMMF
    Coastal Wifi Car parking on site Pub within 1 mile Detached Garden / Patio Ground Floor Facilities Rural Location
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    Knowle Lodge - The Studio

    Cuckfield, near Haywards Heath, Sussex

    8.5 6 reviews
    8.5 6 reviews
    Ref: UKC1599
    Wifi Car parking on site Pub within 1 mile Garden / Patio
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    Knowle Lodge - Petit Knowle
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    Kiln Cottage

    Rye, Sussex

    23/05/2019
    9.2 19 reviews
    9.2 19 reviews
    Ref: W43953
    Coastal Wifi Car parking on site Enclosed Garden / Patio Pub within 1 mile Pets go free
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    Larkspur

    St Leonards-on-Sea, near Hastings, Sussex

    09/06/2019
    9.4 20 reviews
    9.4 20 reviews
    Ref: UKC1890
    Coastal Wifi Enclosed Garden / Patio Pub within 1 mile Pets go free Coast within 1 mile Garden / Patio
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    Knowle Lodge - Petit Knowle

    Cuckfield, near Haywards Heath, Sussex

    9.4 8 reviews
    9.4 8 reviews
    Ref: UKC2003
    Wifi Car parking on site Pub within 1 mile Detached Garden / Patio Ground Floor Facilities
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