01929 481547
beautiful dorset landscape to be enjoyed on a dorset holiday
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.

Subscribe to our Newsletter
Find an October Half Term

Holiday Cottage in Dorset

Ridgeview Cottage image
Ridgeview Cottage
Corfe Castle
4.5/5
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
18th - 23rd October  £965.23
17th - 24th October  £1,105.00
+18 more stays
View & Book
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
23rd - 24th October  £920.54
17th - 24th October  £1,422.40
17th - 22nd October  £1,422.40
+25 more stays
View & Book
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 - 20th October  £923.70
17th - 24th October  £1,260.00
20th - 24th October  £1,054.60
+2 more stays
View & Book
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  £580.05
18th - 24th October  £919.45
17th - 21st October  £713.85
+18 more stays
View & Book
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
22nd - 24th October  £285.00
18th - 24th October  £800.00
17th - 21st October  £535.00
+18 more stays
View & Book
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  £579.24
19th - 22nd October  £654.37
18th - 23rd October  £894.75
+25 more stays
View & Book
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
View & Book
Froxfield Cottage image
Froxfield Cottage
Langton Matravers
4.9/5
3 Bedrooms. Froxfield Cottage is a cosy renovated quarryman’s cottage built in the 1850’s, sympathetically decorated in a mix of contemporary and traditional style.
6
3
2
1
17th - 24th October  £893.50
View & Book
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  £800.80
19th - 23rd October  £913.19
18th - 20th October  £800.80
+12 more stays
View & Book
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  £813.84
17th - 19th October  £813.84
17th - 21st October  £928.18
+18 more stays
View & Book
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
19th - 22nd October  £741.02
22nd - 24th October  £741.02
18th - 19th October  £741.02
+25 more stays
View & Book
Sea reach external
Sea Reach
Swanage
4.9/5
2 Bedrooms. We are delighted to introduce Sea Reach, this spacious and modern ground floor apartment is in a prime holiday hotspot, just 3/4 minutes’ walk from the beach.
4
2
1
0
17th - 24th October  £638.05
View & Book
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
18th - 21st October  £671.60
18th - 19th October  £671.60
17th - 22nd October  £920.00
+25 more stays
View & Book
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
19th - 22nd October  £917.31
17th - 24th October  £1,251.25
17th - 22nd October  £1,251.25
+25 more stays
View & Book
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
View & Book
Greenhayes image
Greenhayes
Langton Matravers
4.8/5
Lovely, traditional cottage with stunning country views to the coast. Ideal for a romantic getaway or for small families. Pet friendly.
4
2
1
2
17th - 24th October  £989.80
View & Book
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  £1,141.00
View & Book
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
View & Book
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
View & Book
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  £1,356.25
View & Book
Stay Connected
Subscribe to our newsletter to get the latest updates and offers.