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 October 2025

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As we wrap up an exciting October in Dorset, filled with Halloween celebrations, autumnal landscapes, and seasonal fun, 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 October 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 an October Half Term

Holiday Cottage in Dorset

Save 15% on stays between 30th Aug - 31st Oct
Save 10% on stays before 26th October
holiday home wareham with hot tub
Cherry Lodge
Wareham
4.8/5
9
4
2
2
19th - 24th October  £1,347.06 £1,163.31
23rd - 24th October  £987.26 £853.12
+25 more stays
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Save 20% on stays before 26th October
Save 10% on stays before 9th November
Sandy Shores Apartment image
Sandy Shores Apartment
Swanage
5/5
5
2
1
0
17th - 18th October  £411.80 £340.30
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Brook Cottage image
Brook Cottage
Corfe Castle
4.9/5
6
3
3
0
22nd - 24th October  £911.38 £746.69
20th - 23rd October  £911.38 £746.69
+18 more stays
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1 Westport Cottage Ph3 Web
Westport Cottage
Wareham
4.9/5
5
3
2
0
17th - 22nd October  £875.85 £759.90
19th - 23rd October  £731.92 £634.52
+18 more stays
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Save 15% on stays before 26th October
Sea reach external
Sea Reach
Swanage
4.9/5
4
2
1
0
18th - 22nd October  £518.75 £450.58
20th - 22nd October  £456.71 £397.47
+18 more stays
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Billet Doux
Swanage
5/5
2
1
1
1
20th - 22nd October  £549.75
21st - 23rd October  £549.75
+25 more stays
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Save 15% on stays before 26th October
Tilshead image
Tilshead
Langton Matravers
4.8/5
8
4
3
2
20th - 23rd October  £1,172.18 £1,011.43
18th - 23rd October  £1,600.39 £1,380.19
+12 more stays
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Save 20% on stays before 26th October
IMG 8040 HDR Edit
Denbur Cottage
Gaunts Common
4.8/5
4
2
2
0
20th - 24th October  £666.52 £548.92
17th - 19th October  £586.44 £484.24
+18 more stays
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Beach Approach image
Beach Approach
Swanage
4.8/5
4
2
1
0
17th - 22nd October  £711.21 £649.85
19th - 23rd October  £606.26 £553.51
+18 more stays
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Owl Cottage image
Owl Cottage
Wareham
5/5
4
2
1
1
17th - 21st October  £786.61 £642.07
18th - 20th October  £653.50 £549.50
+25 more stays
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Save 15% on stays before 26th October
Below Decks image
Below Decks
Swanage
4.8/5
6
3
2
2
18th - 20th October  £622.12 £540.52
18th - 21st October  £701.87 £608.79
+12 more stays
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Save 10% on stays before 26th October
Old Orchard House image
Old Orchard House
Wareham
5/5
10
4
2
2
20th - 23rd October  £1,120.90 £1,018.90
22nd - 24th October  £1,120.90 £1,018.90
+7 more stays
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Greenhayes image
Greenhayes
Langton Matravers
4.8/5
4
2
1
2
20th - 24th October  £723.26 £659.31
17th - 24th October  £985.42 £897.82
+25 more stays
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Save 10% on stays before 26th October
Sea Tower image
Sea Tower
Weymouth
4.8/5
6
3
2
0
18th - 20th October  £1,142.06 £1,038.03
23rd - 24th October  £1,142.06 £1,038.03
+18 more stays
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Save 15% on stays before 26th October
big cottage in swanage exterior and gardens
Lizards Rest
Swanage
4.7/5
9
4
2
0
20th - 24th October  £970.97
21st - 23rd October  £858.04
+18 more stays
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Save 10% on stays before 26th October
Lulwind image
Lulwind
Lulworth Cove
4.8/5
5
3
2
2
19th - 24th October  £1,146.35 £1,043.35
20th - 24th October  £959.13 £872.61
+3 more stays
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Underhill
Nr Corfe Castle
5/5
7
4
3
3
19th - 20th October  £1,170.00
18th - 24th October  £1,610.00
+25 more stays
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Bluebell Cottage
Dorchester
5/5
3
2
1
1
17th - 19th October  £444.50
17th - 20th October  £476.25
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Jasmine Cottage
Dorchester
0/5
4
2
1
0
17th - 19th October  £553.70
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Save 20% on stays before 26th October
Heathlands image
Heathlands
Studland
4.6/5
6
3
1
0
18th - 21st October  £800.80
21st - 23rd October  £800.80
+18 more stays
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