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

Save 20% on stays before 23rd September
Save 15% on stays before 7th October
Sea reach external
Sea Reach
Swanage
4.9/5
4
2
1
0
27th - 29th September  £417.42 £369.45
26th - 29th September  £417.42 £369.45
+3 more stays
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West Lodge image
West Lodge
Church Knowle, Nr Corfe Castle
4.9/5
10
5
3
0
23rd - 26th September  £803.25 £728.43
19th - 21st September  £803.25 £728.43
+18 more stays
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Seacombe Ph40 Web
Seacombe
Langton Matravers
4.9/5
8
4
3
2
28th - 30th September  £840.66
27th - 29th September  £840.66
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Newton House image
Newton House
Swanage
4.6/5
6
3
2
0
28th - 30th September  £485.01
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Angel Cottage image
Angel Cottage
Swanage
4.7/5
2
1
1
2
29th - 30th September  £331.94
27th - 28th September  £331.94
+3 more stays
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IMG 5608 HDR Edit
Malvern Apartment
Swanage
4.5/5
2
1
1
0
28th - 30th September  £356.36 £344.25
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IMG 7696
Daisy’s
Swanage
4.7/5
6
3
3
1
21st - 26th September  £841.00
20th - 21st September  £617.83
+19 more stays
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Save 30% on stays before 7th October
Save 20% on stays before 21st October
Bucknowle Lodge image
Bucknowle Lodge
Church Knowle
4.8/5
8
4
3
2
17th - 22nd September  £1,470.00 £1,056.00
18th - 24th September  £1,642.50 £1,176.75
+23 more stays
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IMG 8040 HDR Edit
Denbur Cottage
Gaunts Common
4.8/5
4
2
2
0
25th - 30th September  £632.64 £524.44
14th - 20th September  £611.00 £448.70
+114 more stays
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The Lookout image
The Lookout
Silverlake
5/5
10
4
4
0
20th - 25th September  £2,070.00 £1,872.50
21st - 23rd September  £1,595.00
+62 more stays
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Save 10% on stays before 21st October
The Aspens image
The Aspens
Swanage
4.7/5
5
2
2
0
27th - 30th September  £465.73 £386.74
26th - 29th September  £465.73 £386.74
+7 more stays
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Billet Doux image
Billet Doux
Swanage
5/5
3
1
1
1
27th - 29th September  £530.85
28th - 29th September  £530.85
+4 more stays
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Orchid House image
Orchid House
Langton Matravers
4.9/5
8
4
3
2
22nd - 30th September  £1,255.71 £1,139.14
22nd - 27th September  £1,090.00 £967.60
+52 more stays
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Compass Cottage image
Compass Cottage
Swanage
4.9/5
4
2
1
1
24th - 28th September  £759.00 £687.60
23rd - 29th September  £867.50 £786.75
+42 more stays
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Save 10% on stays before 7th October
Purbeck Escape image
Purbeck Escape
Swanage
4.8/5
6
3
2
0
28th - 30th September  £532.53
27th - 29th September  £532.53
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Owl Cottage image
Owl Cottage
Wareham
5/5
4
2
1
1
22nd - 30th September  £1,399.40 £1,132.52
25th - 27th September  £569.90 £559.50
+34 more stays
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1 Westport Cottage Ph3 Web
Westport Cottage
Wareham
4.9/5
5
3
2
0
27th - 29th September  £615.11 £534.52
26th - 29th September  £615.11 £534.52
+3 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
10th - 11th September  £778.25 £703.42
+13 more stays
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Bayview
Swanage
5/5
5
3
2
2
25th - 30th September  £868.79
25th - 26th September  £665.84
+12 more stays
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Dorset Farmhouse image
Dorset Farmhouse
Portesham, Nr Abbotsbury
4.8/5
6
3
2
0
18th - 20th September  £702.00 £582.60
22nd - 26th September  £708.75 £612.94
+40 more stays
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