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Sun 26 Oct 25
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Kent • Sun 26 Oct 25 • Guests

October half-term breaks in Kent

278 properties found

Rolvenden, Kent

Hexden Lea

211

Our grading

Sat 25 Oct 2025

7 nights

Sat 25 Oct 2025

£629

Was £653

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Wadhurst, Sussex

Treetops at Bewl Water

211

Our grading

Fri 24 Oct 2025

7 nights

Fri 24 Oct 2025

£788

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Tenterden, Kent

The Lookers Legacy

2111

Our grading

Fri 24 Oct 2025

7 nights

Fri 24 Oct 2025

£1,029

Was £1,048

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Luddesdown, Kent

Darnley Lodge

2111

Our grading

Fri 24 Oct 2025

7 nights

Fri 24 Oct 2025

£723

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Chillenden, near Canterbury, Kent

The Griffins Retreat

211

Our grading

Fri 24 Oct 2025

7 nights

Fri 24 Oct 2025

£877

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Benenden, near Cranbrook, Kent

Little Swaylands

2112

Our grading

Fri 24 Oct 2025

7 nights

Fri 24 Oct 2025

£833

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Hythe, Kent

Coastal Nest - Hythe

211

Our grading

Fri 24 Oct 2025

7 nights

Fri 24 Oct 2025

£749

Was £799

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Bodiam, near Robertsbridge, Sussex

The Lady Stella

2112

Our grading

Fri 24 Oct 2025

7 nights

Fri 24 Oct 2025

£572

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Bodiam, near Robertsbridge, Sussex

Lady Jane

2112

Our grading

Fri 24 Oct 2025

7 nights

Fri 24 Oct 2025

£547

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Biddenden, Kent

The Apple Barn

2112

Our grading

Fri 24 Oct 2025

7 nights

Fri 24 Oct 2025

£671

Was £704

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Northiam, near Rye, Sussex

Elsie Cottage

2111

Our grading

Fri 24 Oct 2025

7 nights

Fri 24 Oct 2025

£622

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Bodiam, Sussex

Jessie's Place

211

Our grading

Sat 01 Nov 2025

7 nights

Sat 01 Nov 2025

£419

Was £429

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Showing 1-12 of 278 properties

Kent cottages for October half-term

Embrace autumn together this October half term in one of our fantastic handpicked properties in Kent. With the vibrant colours of autumn, this ‘Garden of England’ with its natural beauty and 350 miles of coastline is a true spectacle, providing the ultimate backdrop for creating great memories on a family staycation.

With holiday cottages to suit everyone from cosy seaside properties in Whitstable to barn conversions in rural idylls, you’re guaranteed to find your ideal Kent getaway this October half term.

Whether you’re looking to spend some quality family time this October half term or you fancied whisking the whole brood away for a short break, you’ll find the ideal Kent cottage amongst our collection. Some of our cottages also have late availability enabling you to be spontaneous and get away for less.