Dorset Cottage Holidays, holiday homes to rent in Dorset
Discover

What's on in Dorset in October 2025

Keep up to date with Dorset

SUBSCRIBE TO OUR NEWSLETTER

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

Capstone
Swanage
5/5
8
4
2
0
17th - 19th October  £763.75
19th - 21st October  £763.75
22nd - 24th October  £763.75
+25 more stays
View & Book
Juniper Cottage
West Lulworth
4.9/5
5
2
1
2
19th - 21st October  £720.28
19th - 23rd October  £834.62
17th - 19th October  £720.28
+18 more stays
View & Book
Billet Doux
Swanage
5/5
3
1
1
1
22nd - 24th October  £549.75
20th - 22nd October  £549.75
18th - 21st October  £636.38
+25 more stays
View & Book
The Wedge
Swanage
4.9/5
6
3
2
1
23rd - 24th October  £920.54
19th - 20th October  £920.54
17th - 23rd October  £1,422.40
+25 more stays
View & Book
Valley View
Swanage
4.5/5
8
4
3
2
20th - 22nd October  £1,248.85
17th - 24th October  £2,059.75
18th - 24th October  £1,860.78
+25 more stays
View & Book
Stone Quay Cottage
Swanage
4.9/5
3
2
1
2
20th - 22nd October  £287.50
18th - 24th October  £827.50
17th - 24th October  £958.75
+18 more stays
View & Book
Heathlands
Studland
4.6/5
6
3
1
0
21st - 24th October  £800.80
18th - 20th October  £800.80
18th - 23rd October  £1,091.65
+12 more stays
View & Book
Dorset Farmhouse
Portesham, Nr Abbotsbury
5/5
6
3
2
0
19th - 21st October  £702.00
20th - 22nd October  £702.00
21st - 22nd October  £702.00
+25 more stays
View & Book
St Marks Cottage
Swanage
5/5
4
2
2
0
18th - 21st October  £741.02
23rd - 24th October  £741.02
17th - 18th October  £741.02
+25 more stays
View & Book
West Lodge
Church Knowle, Nr Corfe Castle
4.9/5
10
5
3
0
17th - 24th October  £1,681.75
View & Book
Newton House
Swanage
4.6/5
6
3
2
0
17th - 19th October  £580.05
17th - 22nd October  £867.37
21st - 24th October  £675.10
+18 more stays
View & Book
Seaspray
Swanage
5/5
5
3
2
0
17th - 24th October  £1,009.75
View & Book
Sea Tower
Weymouth
5/5
6
3
2
0
17th - 20th October  £955.64
22nd - 23rd October  £1,147.26
18th - 22nd October  £1,311.85
+18 more stays
View & Book
Old Stone House
Swanage
4.8/5
7
3
2
2
18th - 21st October  £740.18
17th - 19th October  £740.18
21st - 22nd October  £740.18
+25 more stays
View & Book
Coastguard Cottage
Worth Matravers
4.6/5
8
4
3
0
17th - 24th October  £1,016.05
View & Book
Littlecot
Weymouth
5/5
8
4
2
2
20th - 23rd October  £888.70
17th - 19th October  £888.70
17th - 24th October  £1,210.00
+2 more stays
View & Book
Bronte Cottage
Wareham
4.8/5
4
3
2
1
17th - 24th October  £842.80
View & Book
Honeysuckle Cottage
Kingston, Nr Corfe Castle
4.8/5
6
3
2
2
17th - 24th October  £1,178.80
View & Book
Compass Cottage
Swanage
4.9/5
4
2
1
1
17th - 18th October  £616.20
View & Book
Greenhayes
Langton Matravers
4.8/5
4
2
1
2
17th - 24th October  £989.80
View & Book