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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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    Larkspur

    St Leonards-on-Sea, near Hastings, Sussex

    9.4 18 reviews
    9.4 18 reviews
    Ref: UKC1890
    Coastal Wifi Enclosed Garden / Patio Pub within 1 mile Coast within 1 mile Garden / Patio
    2
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    Little Ponds

    Cross In Hand, near Heathfield, Sussex

    9.5 17 reviews
    9.5 17 reviews
    Ref: UKC129
    Wifi Car parking on site Pub within 1 mile Detached Garden / Patio
    6
    3
    2
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    The Buttery

    Guestling, Sussex

    7.5 2 reviews
    7.5 2 reviews
    Ref: M490022
    Luxury Wifi Car parking on site Rural Location
    2
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    Newly listed

    Newhope

    Winchelsea Beach, near Rye, Sussex

    0 0 reviews
    0 0 reviews
    Ref: UK12299
    Coastal Car parking on site Enclosed Garden / Patio Pub within 1 mile Coast within 1 mile Detached Garden / Patio
    2
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    Knowle Lodge - Petit Knowle

    Cuckfield, near Haywards Heath, Sussex

    9 5 reviews
    9 5 reviews
    Ref: UKC2003
    Wifi Car parking on site Pub within 1 mile Detached Garden / Patio Ground Floor Facilities
    2
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    Henley Cottage

    Catsfield, near Battle, Sussex

    8.9 11 reviews
    8.9 11 reviews
    Ref: POOT
    Luxury Wifi Car parking on site Detached Garden / Patio Ground Floor Facilities Rural Location Woodburning Stove
    2
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    Lower Marley Farm - Quince Cottage

    Sedlescombe, near Battle, Sussex

    8.6 14 reviews
    8.6 14 reviews
    Ref: 27443
    Coastal Wifi Car parking on site Enclosed Garden / Patio Pub within 1 mile Garden / Patio Rural Location
    2
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    Lower Marley Farm - Apple Cottage
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    5 The Boathouse

    Rye, Sussex

    7.3 6 reviews
    7.3 6 reviews
    Ref: UKC654
    Coastal Wifi Car parking on site Pub within 1 mile
    2
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    The Nissen

    Tenterden, Kent

    10 1 reviews
    10 1 reviews
    Ref: M550129
    Luxury Wifi Car parking on site Enclosed Garden / Patio Rural Location
    2
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    Beaton Studio

    Fairlight, Sussex

    0 0 reviews
    0 0 reviews
    Ref: M408370
    Coastal Wifi Car parking on site Enclosed Garden / Patio Coast within 1 mile Garden / Patio Rural Location
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    Water’s Edge

    Rolvenden Layne, near Tenterden, Kent

    8.6 8 reviews
    8.6 8 reviews
    Ref: PNNO
    Car parking on site Pub within 1 mile Detached Garden / Patio Rural Location
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    Windmill Barn

    Windmill Hill, near Hailsham, Sussex

    9.9 31 reviews
    9.9 31 reviews
    Ref: UKC2485
    Luxury Wifi Car parking on site Pub within 1 mile Detached Garden / Patio Woodburning Stove
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