Dorset Cottage Holidays, holiday homes to rent in Dorset
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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

Greenhayes
Langton Matravers
4.8/5
4
2
1
2
26th - 29th September  £603.81
19th - 26th September  £821.80
19th - 28th September  £1,056.60
+5 more stays
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Compass Cottage
Swanage
4.9/5
4
2
1
1
23rd - 24th September  £616.20
22nd - 26th September  £794.70
23rd - 26th September  £696.52
+42 more stays
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Little Strouds
Sturminster Newton
5/5
2
1
1
2
28th - 29th September  £124.25
13th - 26th September  £1,341.81
3rd - 10th September  £836.23
+312 more stays
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Billet Doux
Swanage
5/5
3
1
1
1
20th - 22nd September  £530.85
4th - 14th September  £1,576.00
28th - 29th September  £530.85
+312 more stays
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The Old Butcher’s Cottage
Corfe Castle
4.9/5
6
3
2
2
13th - 20th September  £1,243.90
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Westport Cottage
Wareham
4.9/5
5
3
2
0
27th - 30th September  £619.14
28th - 30th September  £619.14
26th - 28th September  £619.14
+3 more stays
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Juniper Cottage
West Lulworth
4.9/5
5
2
1
2
27th - 29th September  £527.50
26th - 29th September  £569.50
19th - 26th September  £805.00
+9 more stays
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Stone Quay Cottage
Swanage
4.9/5
3
2
1
2
28th - 30th September  £287.50
21st - 27th September  £932.50
26th - 29th September  £418.75
+53 more stays
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Markham House
Weymouth
5/5
5
3
2
1
27th - 30th September  £686.45
5th - 12th September  £1,070.00
26th - 27th September  £686.45
+10 more stays
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Sea Tower
Weymouth
5/5
6
3
2
0
27th - 30th September  £955.64
20th - 27th September  £1,303.75
20th - 28th September  £2,204.39
+7 more stays
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Honeysuckle Cottage
Kingston, Nr Corfe Castle
4.8/5
6
3
2
2
12th - 19th September  £1,367.80
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Sea Reach
Swanage
4.9/5
4
2
1
0
19th - 26th September  £549.00
12th - 19th September  £601.00
12th - 26th September  £1,110.00
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Harbour Vista
Weymouth
5/5
4
2
2
0
27th - 28th September  £536.75
20th - 28th September  £1,365.50
26th - 28th September  £674.04
+16 more stays
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Hill View
Weymouth
5/5
4
2
1
1
25th - 28th September  £629.37
5th - 12th September  £1,114.75
25th - 29th September  £721.19
+73 more stays
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Garden Flat
Swanage
5/5
4
2
2
0
28th - 29th September  £542.20
20th - 29th September  £1,376.70
20th - 27th September  £821.25
+11 more stays
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Dorset Farmhouse
Portesham, Nr Abbotsbury
5/5
6
3
2
0
29th - 30th September  £630.00
2nd - 4th September  £822.00
4th - 5th September  £822.00
+25 more stays
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Seacombe
Langton Matravers
4.9/5
8
4
3
2
27th - 30th September  £840.66
28th - 30th September  £840.66
27th - 29th September  £840.66
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St Marks Cottage
Swanage
5/5
4
2
2
0
24th - 27th September  £725.69
24th - 29th September  £988.75
23rd - 29th September  £988.75
+42 more stays
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Castle View House
Corfe Castle
5/5
9
5
4
1
5th - 12th September  £2,479.75
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Newton House
Swanage
4.6/5
6
3
2
0
22nd - 25th September  £485.01
20th - 22nd September  £485.01
23rd - 25th September  £485.01
+8 more stays
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