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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

Old Stone House image
Old Stone House
Swanage
4.8/5
If you want to stay in well proportioned, historic cottage by the sea - The Old Stone has to be at the top of your list.
7
3
2
2
17th - 20th October  £671.60
21st - 23rd October  £671.60
20th - 21st October  £671.60
+25 more stays
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3 Puddledock Cottage image
3 Puddledock Cottage
Sutton Poyntz, Nr Weymouth
5/5
Enjoy soaking up the Dorset sunshine in this newly renovated countryside cottage, tucked away in the quiet village of Sutton Poyntz.
6
3
1
0
17th - 24th October  £1,070.65
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Markham House image
Markham House
Weymouth
5/5
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  £1,114.75
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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  £827.05
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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
18th - 20th October  £285.00
20th - 23rd October  £410.00
18th - 24th October  £800.00
+18 more stays
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St Marks Cottage image
St Marks Cottage
Swanage
5/5
Come and stay in this beautifully appointed cottage, ideal for families and cottage in a quiet spot in the town - walk to beach and coastal path.
4
2
2
0
17th - 20th October  £741.02
21st - 23rd October  £741.02
22nd - 23rd October  £741.02
+25 more stays
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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
20th - 23rd October  £813.84
18th - 20th October  £813.84
18th - 21st October  £813.84
+18 more stays
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Sea Tower image
Sea Tower
Weymouth
0/5
Breathtaking holiday home with wide ranging coastal views and exquisite interior for a luxury break.
6
3
2
0
17th - 20th October  £857.75
18th - 20th October  £1,040.25
20th - 21st October  £1,040.25
+18 more stays
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Castle View House image
Castle View House
Corfe Castle
5/5
Escape the ordinary at Castle View House, a haven in the countryside that accommodates up to nine guests. With its enchanting views of Corfe Castle, stylish open-plan interiors, and dog-friendly atmosphere, this residence promises a unique and memorable retreat. Nestled in the heart of Corfe Castle village, it provides an ideal setting for switching off from the demands of everyday life and savoring every moment with friends and family. Whether you're captivated by the historic charm of the surroundings or indulging in the comfort of the stylish interiors, Castle View House invites you to create lasting memories in a tranquil and welcoming escape.
9
5
4
1
17th - 24th October  £2,319.10
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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  £988.75
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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
22nd - 23rd October  £579.24
18th - 22nd October  £746.19
17th - 21st October  £746.19
+25 more stays
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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  £1,383.55
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The Wedge image
The Wedge
Swanage
4.9/5
A spacious 3 bedroom bungalow, set on the cliff top in a private part of Swanage overlooking picturesque Purbeck Hills. Situated just outside of the town centre on a quiet road but with all amenities nearby, this holiday home is within a short walk of the beach. It is ideal for those wishing to explore most spectacular walks and enjoy the scenery of a pretty coastline.
6
3
2
1
19th - 20th October  £920.54
18th - 24th October  £1,422.40
19th - 24th October  £1,422.40
+25 more stays
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1 Westport Cottage Ph3 Web
Westport Cottage
Wareham
4.9/5
3 bedrooms. A distinctive period holiday cottage to rent in Wareham, in a unique location with tastefully presented interior. This is one of only three cottages built on top of the old Saxon walls in Wareham.
5
3
2
0
17th - 24th October  £881.65
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Honeysuckle Cottage image
Honeysuckle Cottage
Kingston, Nr Corfe Castle
4.8/5
This two-bedroom + annex Purbeck stone cottage is tucked away in the very quiet village of Kingston, near Corfe Castle. Escape the everyday, with luxury interiors and enhancing views! Pet-friendly.
6
3
2
2
17th - 24th October  £1,178.80
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Elizabeth Cottage image
Elizabeth Cottage
Lulworth Cove,
5/5
2 bed chocolate box thatched cottage. Ideal for a romantic break by the sea. Just a short walk to Lulworth Cove.
4
2
2
1
17th - 24th October  £820.75
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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  £1,009.75
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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
18th - 21st October  £917.31
17th - 19th October  £917.31
17th - 24th October  £1,251.25
+25 more stays
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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
18th - 21st October  £800.80
20th - 24th October  £913.19
22nd - 24th October  £800.80
+12 more stays
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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  £713.65
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