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Kent and Sussex • Dates • Guests
Kent and Sussex • Dates • Guests

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£1,500+
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Cottages for May Half Term

529 properties found
Goudhurst, near Cranbrook, Kent

Smugley Cottage

211

Our grading

7 nights

£462 - £762

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Maidstone, Kent

Squirrels Oak - Shepherds Hut 1

2111

Our grading

7 nights

£800 - £864

View
Rolvenden, near Cranbrook, Kent

The Nissen

211

Our grading

7 nights

£794 - £1,088

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Luddesdown, near Gravesend, Kent

Darnley Lodge

2111

Our grading

7 nights

£558 - £872

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Ashburnham, near Battle, Sussex

Little Midge Barn

211

Our grading

7 nights

£556 - £968

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Benenden, near Cranbrook, Kent

The Secret Hideaway

211

Our grading

7 nights

£804 - £864

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Challock, near Ashford, Kent

The Old Post Office

2112

Our grading

7 nights

£603 - £868

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Ninfield near Battle, Sussex

The Shepherd's Retreat

211

Our grading

7 nights

£590 - £872

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Birchington-on-Sea, Kent

Stable Barn Cottages - Unit 1

2111

Our grading

7 nights

£624 - £926

View
Netherfield, near Battle, Sussex

Little Doctors Cottage

2111

Our grading

7 nights

£530 - £932

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Broadstairs, Kent

Kingsgate Cottage

2112

Our grading

7 nights

£529 - £918

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Etchingham, Sussex

Brand's Cottage

211

Our grading

7 nights

£596 - £900

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Showing 1-12 of 529 properties

May half term holiday cottages and self-catering accommodation

Spring is in full bloom and summer will soon be here! What better time to take a family holiday than May half term? Avoid the summer rush and head to a cosy cottage in Kent or Sussex for an unforgettable escape. From countryside retreats in stunning farmland surroundings to coastal cottages in quaint fishing villages, you will find something just perfect. Whether you’re looking for a short break over May bank holiday or a week-long retreat, head out and explore somewhere new this May.

Find your perfect springtime break from our collection of May half-term cottages above, with everything from dog-friendly self-catering accommodation to romantic holiday homes to choose from.