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

Cottages for May Half Term

177 properties found
Hawkhurst, Kent Countryside

The Stables at Skelcrosse

211

Our grading

Mon 27 May 2024

7 nights

Mon 27 May 2024

£757

View
Stowting, Kent Countryside

Swift

2112

Our grading

Sat 25 May 2024

7 nights

Sat 25 May 2024

£635

Was £644

View
Goudhurst, Kent Countryside

London Hopper Hut

2111

Our grading

Sat 25 May 2024

7 nights

Sat 25 May 2024

£835

View
Eastbourne, Sussex

Dovecote Cottage

211

Our grading

Sat 25 May 2024

7 nights

Sat 25 May 2024

£822

View
Tenterden, Kent

Pocket Cottage

2113

Our grading

Sat 25 May 2024

7 nights

Sat 25 May 2024

£680

View

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Sevenoaks, Kent Countryside

Middle Barn

2111

Our grading

Sat 25 May 2024

7 nights

Sat 25 May 2024

£800

View
Hythe, Kent Coast

Squirrel

211

Our grading

Mon 27 May 2024

7 nights

Mon 27 May 2024

£1,187

View
Benenden, Kent Countryside

The Barn Studio

2111

Our grading

Sat 25 May 2024

7 nights

Sat 25 May 2024

£729

Was £739

View
Kemp Town, Sussex Coast

Maisie's Place

211

Our grading

Sat 25 May 2024

7 nights

Sat 25 May 2024

£747

View
Chillenden, Kent

The Griffins Retreat

211

Our grading

Sun 26 May 2024

7 nights

Sun 26 May 2024

£890

View
Goodnestone, Kent Countryside

The Nut Hatch

211

Our grading

Mon 27 May 2024

7 nights

Mon 27 May 2024

£811

View
Pett, Sussex

The Woodland Wagon

211

Our grading

Sun 26 May 2024

7 nights

Sun 26 May 2024

£806

View
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Showing 1-12 of 177 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.