Destinations and properties
Dates and flexibility
Sun 26 May 24
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Kent and Sussex • Sun 26 May 24 • Guests
Kent and Sussex • Sun 26 May 24 • Guests

Cottages for May Half Term

137 properties found
Benenden, Kent Countryside

The Barn Studio

2111

Our grading

Sat 25 May 2024

7 nights

Sat 25 May 2024

£670

Was £739

View
Pett, Sussex

The Woodland Wagon

211

Our grading

Sun 26 May 2024

7 nights

Sun 26 May 2024

£730

Was £806

View
Tenterden, Kent Countryside

The Lookers Legacy

2111

Our grading

Sun 26 May 2024

7 nights

Sun 26 May 2024

£1,161

View
Goodnestone, Kent Countryside

The Nut Hatch

211

Our grading

Mon 27 May 2024

7 nights

Mon 27 May 2024

£811

View
Hythe, Kent Coast

Squirrel

211

Our grading

Mon 27 May 2024

7 nights

Mon 27 May 2024

£1,187

View

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Tunbridge Wells (3.5mls NE), Kent

The Coach House Tonbridge

211

Our grading

Sat 25 May 2024

7 nights

Sat 25 May 2024

£681

View
Goudhurst, Kent Countryside

Cooks Hopper Hut

2111

Our grading

Sat 25 May 2024

7 nights

Sat 25 May 2024

£677

View
Goudhurst, Kent Countryside

London Hopper Hut

2111

Our grading

Sat 25 May 2024

7 nights

Sat 25 May 2024

£835

View
Benenden, Kent

The Secret Hideaway

211

Our grading

Sun 26 May 2024

7 nights

Sun 26 May 2024

£732

Was £769

View
Sevenoaks, Kent Countryside

Middle Barn

2111

Our grading

Sat 25 May 2024

7 nights

Sat 25 May 2024

£800

View
Brighton, Sussex Coast

Brighton Rock

211

Our grading

Sat 25 May 2024

7 nights

Sat 25 May 2024

£746

View
Eastbourne, Sussex

Dovecote Cottage

211

Our grading

Sat 25 May 2024

7 nights

Sat 25 May 2024

£822

View
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Showing 13-24 of 137 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.