Dorset Cottage Holidays | A cosy, autumn outdoor seating area at a Dorset Holiday Cottage in Sandford.
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What's on in Dorset in September 2025

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As we wrap up an exciting September in Dorset, with its harvest festivals, countryside walks, and crisp autumn air, 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 September 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 a September

Holiday Cottage in Dorset

Stone Quay Cottage
Swanage
4.9/5
3
2
1
2
23rd - 27th September  £585.00
22nd - 28th September  £870.00
+33 more stays
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Save 10% on stays before 16th October
IMG 5608 HDR Edit
Malvern Apartment
Swanage
4.5/5
2
1
1
0
28th - 30th September  £342.11 £330.00
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Sweet Pea Cottage
Nr Dorchester
5/5
4
2
1
1
20th - 22nd September  £574.00
19th - 22nd September  £615.00
+6 more stays
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Ridgeview Cottage image
Ridgeview Cottage
Corfe Castle
4.7/5
6
3
2
0
18th - 22nd September  £790.00
28th - 30th September  £646.30
+6 more stays
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Angel Cottage
Swanage
4.7/5
2
1
1
2
27th - 28th September  £318.28 £263.62
28th - 30th September  £318.28 £263.62
+3 more stays
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Save 30% on stays before 16th October
Save 20% on stays before 30th October
Bucknowle Lodge image
Bucknowle Lodge
Church Knowle
4.7/5
8
4
3
2
19th - 23rd September  £1,287.50 £925.25
19th - 22nd September  £1,115.00 £830.00
+3 more stays
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Juniper Cottage image
Juniper Cottage
West Lulworth
4.9/5
5
2
1
2
20th - 22nd September  £505.00
19th - 22nd September  £545.00
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Sea Breeze
Swanage
5/5
4
2
2
0
28th - 30th September  £509.00
28th - 29th September  £480.00
+7 more stays
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Save 10% on stays before 16th October
West Lodge image
West Lodge
Church Knowle, Nr Corfe Castle
4.9/5
10
5
3
0
19th - 21st September  £803.25 £653.60
20th - 22nd September  £803.25 £653.60
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Save 10% on stays before 16th October
Hill View image
Hill View
Weymouth
5/5
4
2
1
1
28th - 30th September  £600.35 £513.30
28th - 29th September  £600.35 £513.30
+8 more stays
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Heather Cottage
Higher Bockhampton
5/5
6
3
2
1
22nd - 25th September  £975.00
21st - 24th September  £975.00
+8 more stays
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Save 20% on stays before 16th October
Little Strouds image
Little Strouds
Sturminster Newton
5/5
2
1
1
2
20th - 22nd September  £198.58 £162.86
27th - 28th September  £105.00 £100.00
+6 more stays
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Poppy Cottage
Nr Dorchester
0/5
4
2
1
1
20th - 22nd September  £630.00
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Save 20% on stays before 16th October
Brook Cottage image
Brook Cottage
Corfe Castle
4.9/5
6
3
3
0
28th - 30th September  £712.73 £581.18
27th - 29th September  £712.73 £581.18
+3 more stays
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holiday home wareham with hot tub
Cherry Lodge
Wareham
4.8/5
9
4
2
2
25th - 29th September  £1,042.00 £967.97
21st - 29th September  £2,122.75 £1,792.43
+63 more stays
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Bluebell Cottage
Dorchester
5/5
3
2
1
1
27th - 29th September  £504.00
27th - 30th September  £518.75
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Save 15% on stays before 16th October
1 Westport Cottage Ph3 Web
Westport Cottage
Wareham
4.9/5
5
3
2
0
27th - 29th September  £592.28 £484.82
26th - 30th September  £673.24 £549.59
+3 more stays
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Save 15% on stays before 16th October
Save 10% on stays before 30th October
St Marks Cottage image
St Marks Cottage
Swanage
5/5
4
2
2
0
25th - 26th September  £693.75 £597.94
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Old Stone House
Swanage
4.8/5
7
3
2
2
29th - 30th September  £775.95
28th - 29th September  £775.95
+7 more stays
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dog at dog friendly holiday home in weymouth
Markham House
Weymouth
5/5
5
3
2
1
27th - 30th September  £686.45 £623.31
28th - 30th September  £686.45 £623.30
+7 more stays
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