Destinations and properties:
Dates and flexibility:
Sun 25 May 25
Party makeup:
Guests
Dorset • Sun 25 May 25 • Guests

May half-term cottages in Dorset

361 properties found

Charmouth, Dorset

Captain's Cabin

2111

Our grading

Fri 23 May 2025

7 nights

Fri 23 May 2025

£561

Was £619

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Ringwood, Hampshire

The Annexe at Avon Glen

2111

Our grading

Fri 23 May 2025

7 nights

Fri 23 May 2025

£664

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Swanage, Dorset

SeaBreeze Holiday Apartment

211

Our grading

Fri 23 May 2025

7 nights

Fri 23 May 2025

£933

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Salwayash, Dorset

Homeleigh Hut

2111

Our grading

Fri 23 May 2025

7 nights

Fri 23 May 2025

£696

Was £769

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Weymouth, Dorset

Honeypot Cottage - Weymouth

2111

Our grading

Sat 24 May 2025

7 nights

Sat 24 May 2025

£818

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Charmouth (2mls N), Dorset

Stubbs Bridge Woodland - Hazel Hut

2111

Our grading

Fri 23 May 2025

7 nights

Fri 23 May 2025

£775

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Sturminster Newton (2mls SE), Dorset

The Brick Barn - Darknoll Farm

2111

Our grading

Fri 23 May 2025

7 nights

Fri 23 May 2025

£780

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Beaminster (3mls N), Dorset

Daisy - Buckham Mills

2111

Our grading

Sat 24 May 2025

7 nights

Sat 24 May 2025

£727

View

Lyme Regis (2mls NW), Devon

Dove Cottage - Uplyme

2112

Our grading

Sat 24 May 2025

7 nights

Sat 24 May 2025

£952

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Blandford Forum (4mls S), Dorset

Dorset View

2112

Our grading

Fri 23 May 2025

7 nights

Fri 23 May 2025

£707

Was £780

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Bridport, Dorset

The Dairy At Wanderwell

211

Our grading

Sat 24 May 2025

7 nights

Sat 24 May 2025

£727

View

Swanage, Dorset

Arnewood

211

Our grading

Fri 23 May 2025

7 nights

Fri 23 May 2025

£701

View

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Showing 1-12 of 361 properties

May half-term holidays in Dorset

There’s a wonderfully wide and varied choice of May half-term cottages in Dorset, a spectacular coastal county in the South West. With its stunning coastline, beautiful rural landscapes and thriving seaside towns, Dorset makes a tranquil and idyllic holiday destination for couples, friends and families in search of excellent self-catering accommodation.

Dorset May half-term cottage inspiration

The fantastic variety of May half-term holiday cottages in Dorset includes tranquil country houses, stylish coastal apartments, pretty family cottages, stone farmhouses, traditional rural retreats and delightfully re-imagined barn conversions. Dorset cottages are perfect half-term holiday homes, providing the ideal base for exploring both the Dorset and Cranborne Chase Areas of Outstanding Natural Beauty which encompass the county, and the Jurassic Coast World Heritage Site, which stretches from Studland Bay to Exmouth. Fancy getting away another time of year? We have Dorset cottages with Christmas, New Year and Easter availability, as well as cottages for the October or February half terms.