Dorset Cottage Holidays, holiday homes to rent in Dorset
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What's on in Dorset in May 2025

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As we wrap up an exciting May in Dorset, with its sunny bank holidays, blooming countryside, and lively festivals, we’d like to thank everyone who joined in the fun! While this year’s calendar is coming to a close, we’re already gearing up for an even more thrilling 2025. Stay tuned for next year’s itinerary of must-see events and special offers. Do you want to keep up-to-date with what’s on in May in Dorset this year and the next? Our email newsletter will keep you up-to-date with the ins and outs of our lovely coastal county, including upcoming events, our favourite attractions and landmarks, and our latest accommodation offers. Sign up today and be the first to hear about what’s happening in 2025!

Find your perfect

May Half Term Cottage

Save 15% on stays before 27th June
Save 10% on stays before 11th July
St Marks Cottage image
St Marks Cottage
Swanage
5/5
4
2
2
0
30th - 31st May  £657.25 £566.91
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Save 15% on stays before 27th June
Seaspray image
Seaspray
Swanage
5/5
5
3
2
0
30th - 31st May  £681.34 £587.39
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Save 20% on stays before 6th June
Save 10% on stays before 27th June
Orchid House image
Orchid House
Langton Matravers
4.9/5
8
4
3
2
30th May - 1st June  £949.25 £770.40
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Save 20% on stays before 6th June
Save 10% on stays before 27th June
Compass Cottage image
Compass Cottage
Swanage
4.9/5
4
2
1
1
30th - 31st May  £395.00 £325.00
31st May - 1st June  £509.00 £416.20
30th May - 1st June  £811.50 £658.20
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Save 15% on stays before 27th June
IMG 7696
Daisy’s
Swanage
4.7/5
6
3
3
1
31st May - 1st June  £686.45
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Save 20% on stays before 8th August
Save 20% on stays before 27th June
Littlecot image
Littlecot
Weymouth
5/5
8
4
2
2
30th - 31st May  £839.20 £675.36
30th May - 1st June  £954.40 £767.52
31st May - 1st June  £839.20 £675.36
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Save 10% on stays before 11th July
Capstone image
Capstone
Swanage
5/5
8
4
2
0
31st May - 1st June  £652.00 £592.30
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Save 20% on stays before 6th June
Save 10% on stays before 27th June
Harbour Vista image
Harbour Vista
Weymouth
5/5
4
2
2
0
31st May - 1st June  £605.00 £500.00
30th - 31st May  £677.00 £557.60
30th May - 1st June  £806.35 £661.08
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Save 20% on stays before 27th June
Little Strouds image
Little Strouds
Sturminster Newton
5/5
2
1
1
2
30th - 31st May  £120.00 £115.00
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Save 20% on stays before 13th June
Angel Cottage
Angel Cottage
Swanage
4.7/5
2
1
1
2
31st May - 1st June  £420.68 £345.54
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Save 20% on stays before 6th June
Save 10% on stays before 27th June
holiday home wareham with hot tub
Cherry Lodge
Wareham
4.8/5
9
4
2
2
31st May - 1st June  £985.75 £799.60
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Save 10% on stays before 13th June
Billet Doux image
Billet Doux
Swanage
5/5
3
1
1
1
30th May - 1st June  £447.00 £405.30
31st May - 1st June  £447.00 £405.30
30th - 31st May  £447.00 £405.30
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Save 20% on stays before 27th June
Owl Cottage image
Owl Cottage
Wareham
0/5
4
2
1
1
31st May - 1st June  £490.00
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