Dorset Cottage Holidays, holiday homes to rent in Dorset
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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

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 - 23rd October  £800.80
21st - 24th October  £800.80
+12 more stays
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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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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
20th - 23rd October  £741.02
17th - 18th October  £741.02
22nd - 23rd October  £741.02
+25 more stays
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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
21st - 24th October  £813.84
17th - 22nd October  £1,109.50
+18 more stays
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Garden Flat
Swanage
5/5
Gorgeous, ground floor flat in Swanage with parking and a garden.
4
2
2
0
18th - 19th October  £508.60
19th - 20th October  £508.60
17th - 19th October  £572.65
+18 more stays
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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
21st - 24th October  £740.18
20th - 24th October  £846.44
22nd - 24th October  £740.18
+25 more stays
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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  £1,681.75
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Ridgeview Cottage
Corfe Castle
4.6/5
Located in the sought-after National Trust-owned village of Corfe Castle, Ridgeview Cottage is a modern, detached, family home found moments away from many of Dorset’s prolific attractions.
6
3
2
0
17th - 19th October  £754.44
17th - 22nd October  £929.07
21st - 23rd October  £833.00
+18 more stays
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Compass Cottage
Swanage
4.9/5
A boutique, contemporary seaside cottage, nestled in the heart of the town centre of Swanage.
4
2
1
1
17th - 18th October  £616.20
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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
22nd - 23rd October  £920.54
18th - 22nd October  £1,191.02
17th - 23rd October  £1,422.40
+25 more stays
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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
20th - 22nd October  £287.50
17th - 20th October  £418.75
17th - 24th October  £958.75
+18 more stays
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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  £580.05
20th - 22nd October  £675.10
19th - 23rd October  £768.54
+18 more stays
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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 - 20th October  £932.14
20th - 24th October  £1,069.58
17th - 19th October  £932.14
+2 more stays
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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  £1,254.40
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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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Dream Cottage
Portland
5/5
One of our dream cottages a stylish, compact cottage - ideal for friends and small families to get together to enjoy the coast, walking and watersports.
6
3
2
0
19th - 20th October  £579.24
20th - 21st October  £579.24
18th - 20th October  £654.37
+25 more stays
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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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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  £703.65
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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
17th - 20th October  £917.31
17th - 21st October  £1,047.25
19th - 21st October  £917.31
+25 more stays
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Bucknowle Lodge
Church Knowle
5/5
Beautiful, spacious Dorset lodge for large parties. Within walking distance of Corfe Castle and a short drive to the coast.
8
4
3
2
17th - 24th October  £2,216.25
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