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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.

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Find an October Half Term

Holiday Cottage in Dorset

Dream Cottage image
Dream Cottage
Portland
5/5
A stylish, compact cottage - ideal for friends and small families to get together to enjoy the coast, walking and watersports.
6
3
2
0
17th - 18th October 2025  £579.24
18th - 21st October 2025  £654.37
19th - 22nd October 2025  £654.37
+25 more stays
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Coastguard Cottage image
Coastguard Cottage
Worth Matravers
4.6/5
A lovely semi-detached cottage in the much sought after village of Worth Matravers, within walking distance of the Jurassic Coast.
8
4
3
0
17th - 24th October 2025  £1,016.05
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The Aspens image
The Aspens
Swanage
4.8/5
Delightful light-filled family holiday home, situated just a stone’s throw from beautiful Swanage Pier.
5
2
2
0
17th - 24th October 2025  £713.65
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Bronte Cottage image
Bronte Cottage
Wareham
4.8/5
3 Bedrooms. Bronte Cottage is a charming holiday cottage in Wareham, hidden away in a fabulous location a few strides from Wareham Quay and the river Frome.
4
3
2
1
17th - 24th October 2025  £842.80
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Heathlands image
Heathlands
Studland
4.6/5
3 bedrooms. Heathlands is a modern cottage, the ideal base for family holidays in Studland. This light and airy holiday home is a short walk from Studlands long sandy beach.
6
3
1
0
21st - 24th October 2025  £800.80
20th - 24th October 2025  £913.19
18th - 23rd October 2025  £1,091.65
+12 more stays
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Markham House image
Markham House
Weymouth
0/5
A spacious family home with off road parking and large, enclosed garden. The house is ideal for family and friends who want to stroll through the town to the Harbour and beach.
5
3
2
1
17th - 24th October 2025  £1,114.75
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Hill View image
Hill View
Weymouth
5/5
Set in the peaceful Weymouth suburb of Preston, Hill View offers a delightful retreat for couples or small families.
4
2
1
1
17th - 24th October 2025  £988.75
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Capstone image
Capstone
Swanage
5/5
A beautiful Edwardian home, which is an ideal base for friends and extended family to share adventures on the South coast. Two minute flat walk from beach and town.
8
4
2
0
20th - 23rd October 2025  £876.25
17th - 21st October 2025  £1,000.00
17th - 19th October 2025  £876.25
+25 more stays
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Littlecot image
Littlecot
Weymouth
5/5
A gorgeous, detached family home within stones throw of Smallmouth Bay and the Rodwell trail. Ideal for those who want a comfy base for friends or extended family.
8
4
2
2
17th - 24th October 2025  £1,260.00
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Newton House image
Newton House
Swanage
4.6/5
3 bedrooms. The owners of this spacious seaside home, which is very close to Swanage beach have stylishly furnished with a contemporary and comfortable interior.
6
3
2
0
17th - 19th October 2025  £580.05
20th - 23rd October 2025  £675.10
20th - 22nd October 2025  £675.10
+18 more stays
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Seaspray image
Seaspray
Swanage
5/5
Located steps away from the sandy beach and traditional promenade in Swanage, Seaspray is a three-bedroom, 1930s-style apartment with panoramic sea views. Situated on the wonderful seafront parade, this town centre location is perfect for families or friends seeking a relaxing coastal escape within a stone’s throw of many of Dorset’s prolific attractions.
5
3
2
0
17th - 24th October 2025  £1,009.75
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Orchid House image
Orchid House
Langton Matravers
4.9/5
A delightful four-bedroom holiday accommodation, set right on the doorstep of Dorset’s most breath-taking coastal walks, in the village of Langton Matravers.
8
4
3
2
17th - 24th October 2025  £1,383.55
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Stone Quay Cottage image
Stone Quay Cottage
Swanage
4.9/5
Stone Quay Cottage is right in the heart of the beautiful old fishing town of Swanage, just a stones throw away from the historic Stone Quay, the lovely sandy beaches, the Victorian Pier and all the amenities. This two bedroom cottage dates back to the 1850’s but has been completely renovated to provide a beautiful modern home.
3
2
1
2
21st - 24th October 2025  £673.75
19th - 22nd October 2025  £673.75
17th - 21st October 2025  £770.00
+18 more stays
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Brook Cottage image
Brook Cottage
Corfe Castle
4.8/5
Step back in time and enjoy this delightful semi-detached cottage, exuding charm and character throughout. Built in the early 1730s, this distinctive Grade II red bricked cottage, is set in the heart of the historic village of Corfe Castle. This cosy retreat, nestled in the heart of the Purbecks, would surely be able to tell a tale or two! Sitting peacefully at the bottom of the romantic Castle ruins, you will enjoy morning coffee with arguably one of the most impressive backdrops in Dorset.
6
3
3
0
17th - 24th October 2025  £1,254.40
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Mimosa House image
Mimosa House
Sandford, Wareham
5/5
Mimosa House is a delightful, newly refurbished two-bedroom bungalow, set in a quiet cul-de-sac in Sandford, Wareham. This self-catering accommodation offers plenty of space for a family of 4 and is an ideal spot for a coastal break in Dorset.
4
2
1
0
17th - 24th October 2025  £791.00
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West Lodge image
West Lodge
Church Knowle, Nr Corfe Castle
4.9/5
Tastefully presented and finished to a high standard, this fabulous holiday home in Church Knowle, will appeal to those of you visiting with extended family and friends. Located just a mile outside Corfe Castle, as the crow flies between Kimmeridge Bay and the golden sands of Studland, you will be truly spoilt for things to see and do.
10
5
3
0
17th - 24th October 2025  £1,681.75
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The Bungalow
Little Westport
Wareham
4.8/5
Little Westport is a charming 1960s four-bedroom Colt House, in a peaceful setting with a large garden overlooking the Purbeck Hills. A perfect location for a break to enjoy walking, cycling or exploring the area.
8
4
2
0
17th - 24th October 2025  £1,141.00
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Purbeck Cottage (Kings) image
Purbeck Cottage (Kings)
Swanage
4.7/5
3 bedroom family home with two parking spaces and large covered patio to enjoy outside dining whatever the weather.
6
3
1
0
17th - 18th October 2025  £530.65
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Juniper Cottage image
Juniper Cottage
West Lulworth
4.9/5
Juniper Cottage is a recently refurbished Victorian terraced cottage tucked away off the main road in the scenic village of West Lulworth, close to both Lulworth Cove and one of the Jurassic Coast’s most iconic features, Durdle Door. This two-storey, dog-friendly cottage accommodates up to 4 adults or a family of 5. The ground floor is an open-plan living and dining space with small, private front and rear gardens, upstairs are two bedrooms and a bathroom.
5
2
1
2
19th - 22nd October 2025  £813.84
19th - 21st October 2025  £813.84
22nd - 24th October 2025  £813.84
+18 more stays
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holiday home wareham with hot tub
Cherry Lodge
Wareham
4.7/5
Comfort and space to be enjoyed by friends and family in this large, modern home complete with bubbling hot tub. Its pet friendly and has plenty of parking. The quality of this home and the size of the garden are what attracts guests to Cherry Lodge.
9
4
2
2
17th - 24th October 2025  £1,295.00
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