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Dorset Cottage Holidays | A cosy, autumn outdoor seating area at a Dorset Holiday Cottage in Sandford.
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What's on in Dorset in October 2025

Which Trusted Trader
Your Guide to Autumn Magic, Half Term & Local Events

What’s On in Dorset in October

As October settles over Dorset, the county shifts gear: summer crowds fade, misty mornings drift over heathland, and the landscapes glow with amber and gold. Whether you’re staying in one of our holiday cottages for October Half Term or just planning a day trip, here’s your go-to guide to what’s on in Dorset in October, half term fun, seasonal walks, spooky thrills — and cosy indoor escapes.

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October Events & Activities

Autumn in Dorset is packed with family fun, spooky trails, music festivals, fireworks, and more! Whether you’re chasing Halloween thrills, enjoying local food and drink, or taking in the changing colours of the countryside, there’s plenty to see and do this October – and here our some of the things we are looking forward to the most.

Corfe Castle in October

Corfe Castle in October

Dates: 25th October – 2nd November 2025

Bring your teddy bear (or borrow one) and send them whizzing down the famous teddy zip wire this October Half Term. Families can also take part in a fun-filled quest to find the critters that call Corfe Castle home.

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Gillingham Carnival

Gillingham Carnival

Dates: 28th September – 4th October 2025

 

A week of fun culminating in the spectacular carnival procession on 4th October. Expect floats, music, and plenty of community spirit.

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Swanage Blues Festival

Swanage Blues Festival

Dates: 3rd – 5th October 2025

Enjoy a weekend of open mics, jam sessions and headline blues performances across multiple venues in Swanage.

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Weymouth Oktoberfestfest

Weymouth Oktoberfest

Dates: 3rd – 4th October 2025

Held in the Ocean Room at Weymouth Pavilion on 3rd to 4th October, this seaside beer festival features over sixty real ales and ciders from Dorset and beyond.

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Pirate Festival

Weymouth Pirate Festival

Dates: 3rd – 5th October 2025

Ahoy, matey! Dive into a weekend of pirate antics with live music, cannon fire, and re-enactments. Great family fun in Weymouth – especially if you’re stying in a Weymouth holiday cottage nearby.

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Halloween

Halloween Trail at the Walled Garden in Moreton

Dates: 18th October – 2nd November 2025

Follow a spooky trail through the gardens, complete quizzes, and discover ghostly surprises along the way.

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Halloween Trails in October

Halloween Trails at Minterne Gardens

Dates: 17th – 31st October 2025

Explore the Himalayan Garden filled with pumpkin creatures, spiders, and bats. Treats and home-grown pumpkins await at the end!

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Sherborne Old Castle

Sherborne Castle & Gardens Children’s Pumpkin Trail

Dates: 25th October – 2nd November 2025

Hunt for pumpkins hidden around the castle grounds and solve clues for a prize. Fancy dress welcome!

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Halloween Trail

Halloween at Moors Valley

Dates: 23rd October – 2nd November 2025

A dazzling illuminated Halloween trail with ghostly walks, scarecrows, and delicious food and drink. Perfect for families (and dogs!).

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Swannary

October Half Term at Abbotsbury Swannery

Dates: 25th October – 2nd November 2025


Six spooky games designed for under-10s, including skeleton hunts, spider challenges, and gooey fun. Kids just £1 with a paying adult.

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11

October Half Term at Farmer Palmers

Dates: 25th – 31st October 2025

Enjoy spooky fun for little ones, with daily Halloween activities at this popular family farm park.

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12

Halloween Fun at Monkey World

Date: 31st October 2025

Children in full Halloween costume get free entry! Enjoy themed fun and spooky surprises at this famous rescue centre.

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Find an October Half Term

Holiday Cottage in Dorset

Angel Cottage cosy couples cottage in Swanage Dorset
Angel Cottage
Swanage
4.7/5
2
1
1
2
Nothing is more refreshing than a coastal holiday near the sea and if you’re looking for a cosy, quaint cottage, Angel Cottage should be first on your wishlist. This mid terrace cottage is the perfect base to discover miles of
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Ground Floor Bathroom
Ground Floor Bathroom
Near Supermarket
Near Supermarket
28th - 29th October  £362.86
25th - 31st October  £556.65
+33 more stays
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Westport Cottage image
Westport Cottage
Wareham
4.9/5
5
3
2
0
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.
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Beach Under 5 Miles
Beach Under 5 Miles
Woodburner Provided
Woodburner Provided
Near Supermarket
Near Supermarket
Public transport travel
Public transport travel
23rd - 31st October  £995.40
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Oak Cottage image
Oak Cottage
Weymouth
5/5
4
2
1
2
Characterful two-bedroom cottage with a secluded courtyard garden and beautiful bathroom, close to Dorset's top attractions.
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Woodburner Provided
Woodburner Provided
Walk to Pub
Walk to Pub
26th - 30th October  £707.62
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Forget Me Not Cottage image
Forget Me Not Cottage
Dorchester
4.8/5
4
2
1
0
Forget Me Not Cottage is a cosy 4-Star retreat set within a peaceful Dorset estate, perfect for couples or families. Sleeping four, this dog-friendly two-storey cottage features comfortable interiors, flexible bedrooms, and French doors opening onto the shared gardens and
Hot Tub
Hot Tub
Allocated Parking
Allocated Parking
EV Charge Point
EV Charge Point
Near Supermarket
Near Supermarket
BBQ
BBQ
Bathroom Towels
Bathroom Towels
24th - 28th October  £833.00
24th - 31st October  £1,032.50
+18 more stays
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Lavender Cottage image
Lavender Cottage
Dorchester
5/5
2
1
1
1
Lavender Cottage is a stylish single-storey retreat set within a peaceful Dorset estate, thoughtfully designed for couples seeking rest and relaxation. With a super king bedroom, private enclosed garden, and dog-friendly welcome, it blends modern comfort with countryside charm. Estate
Hot Tub
Hot Tub
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
EV Charge Point
EV Charge Point
Ground Floor Bedroom
Ground Floor Bedroom
Bathroom Towels
Bathroom Towels
26th - 31st October  £736.25
25th - 27th October  £530.00
+25 more stays
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Rose Cottage image
Rose Cottage
Dorchester
5/5
3
2
1
1
Rose Cottage is a welcoming 4-Star ground-floor retreat, perfect for a couple or small family. Sleeping three, this dog-friendly cottage features a light open-plan living space and flexible bedrooms, with shared gardens and hot tubs just outside the door. With
Hot Tub
Hot Tub
Allocated Parking
Allocated Parking
EV Charge Point
EV Charge Point
Ground Floor Bathroom
Ground Floor Bathroom
Ground Floor Bedroom
Ground Floor Bedroom
Near Supermarket
Near Supermarket
24th - 31st October  £970.00
24th - 27th October  £736.25
+25 more stays
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Willow Cottage image
Willow Cottage
Weymouth
5/5
2
1
1
2
Romantic retreat for two with a private wood-fired hot tub, sunny courtyard and easy access to Dorset's coast.
Hot Tub
Hot Tub
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
26th - 31st October  £700.00
26th - 30th October  £560.00
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3 Puddledock Cottage image
3 Puddledock Cottage
Sutton Poyntz, Nr Weymouth
5/5
6
3
1
0
Enjoy soaking up the Dorset sunshine in this newly renovated countryside cottage, tucked away in the quiet village of Sutton Poyntz.
Allocated Parking
Allocated Parking
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Woodburner Provided
Woodburner Provided
Ground Floor Bathroom
Ground Floor Bathroom
Near Supermarket
Near Supermarket
23rd - 26th October  £498.04
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dog at dog friendly holiday home in weymouth
Markham House
Weymouth
5/5
5
3
2
1
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.
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
23rd - 30th October  £1,135.75
23rd - 31st October  £1,232.25
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The Bungalow
Little Westport
Wareham
4.8/5
8
4
2
0
Little Westport is a charming large cottage in Wareham with four-bedroom. This former Colt House, is in a peaceful setting with a large garden overlooking the Purbeck Hills.
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Beach Under 5 Miles
Beach Under 5 Miles
Woodburner Provided
Woodburner Provided
Ground Floor Bathroom
Ground Floor Bathroom
23rd - 30th October  £1,162.00
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Dog Friendly
pretty thatched dorset cottage with wisteria
Milton Cottage
Winfrith Newburgh
5/5
4
2
1
2
A charming thatched cottage in Winfrith Newburgh, perfect for a cosy countryside escape and welcoming dogs for scenic Dorset adventures.
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Beach Under 5 Miles
Beach Under 5 Miles
Woodburner Provided
Woodburner Provided
Public transport travel
Public transport travel
Walk to Pub
Walk to Pub
23rd - 29th October  £810.00
25th - 28th October  £542.50
+33 more stays
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Sea reach external
Sea Reach
Swanage
4.9/5
4
2
1
0
2 Bedrooms. We are delighted to introduce Sea Reach, this spacious and modern ground floor apartment is in a prime place to stay in Swanage, just 3/4 minutes’ walk from the beach.
Allocated Parking
Allocated Parking
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Ground Floor Bathroom
Ground Floor Bathroom
Ground Floor Bedroom
Ground Floor Bedroom
23rd - 31st October  £737.60
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Poppy Cottage image
Poppy Cottage
Dorchester
5/5
4
2
1
1
Poppy Cottage is a welcoming 4-Star Gold retreat designed with families in mind, set within a peaceful Dorset estate. Sleeping four plus a cot, this dog-friendly, single-storey cottage features a light open-plan living space, a secure garden, and a sunny
Hot Tub
Hot Tub
Allocated Parking
Allocated Parking
EV Charge Point
EV Charge Point
Ground Floor Bathroom
Ground Floor Bathroom
Ground Floor Bedroom
Ground Floor Bedroom
Near Supermarket
Near Supermarket
25th - 30th October  £1,157.00
23rd - 30th October  £1,355.00
+12 more stays
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Penlu image
Penlu
Swanage
5/5
4
2
2
0
Central Swanage apartment sleeping four, just a short stroll from the beach, independent shops, cafés and the Jurassic Coast.
Sea Views
Sea Views
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Near Supermarket
Near Supermarket
Walk to Pub
Walk to Pub
23rd - 29th October  £737.50
26th - 31st October  £716.50
+25 more stays
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large holiday cottage near the jurassic coast
Coastguard Cottage
Worth Matravers
4.6/5
8
4
3
0
A lovely semi-detached cottage in the much sought after village of Worth Matravers, within walking distance of the Jurassic Coast.
Allocated Parking
Allocated Parking
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to places to eat
Walk to places to eat
Beach Under 5 Miles
Beach Under 5 Miles
Ground Floor Bathroom
Ground Floor Bathroom
BBQ
BBQ
23rd - 30th October  £1,034.95
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Sweet Pea Cottage
Dorchester
5/5
4
2
1
1
Sweet Pea Cottage is a stylish 4-Star retreat set within a peaceful Dorset estate, perfect for couples, families or friends. Sleeping four, this dog-friendly cottage features a fresh modern interior, flexible bedrooms, and French doors leading to the shared gardens
Hot Tub
Hot Tub
Allocated Parking
Allocated Parking
EV Charge Point
EV Charge Point
Near Supermarket
Near Supermarket
BBQ
BBQ
Bathroom Towels
Bathroom Towels
27th - 30th October  £668.75
27th - 29th October  £620.00
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Ridgeview Cottage image
Ridgeview Cottage
Corfe Castle
4.7/5
6
3
2
0
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.
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Beach Under 5 Miles
Beach Under 5 Miles
EV Charge Point
EV Charge Point
Ground Floor Bathroom
Ground Floor Bathroom
Ground Floor Bedroom
Ground Floor Bedroom
26th - 28th October  £848.33
27th - 29th October  £848.33
+7 more stays
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Greenhayes image
Greenhayes
Langton Matravers
4.8/5
4
2
1
2
Lovely, traditional cottage with stunning country views to the coast. Ideal for a romantic getaway or for small families. Pet friendly.
Sea Views
Sea Views
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Woodburner Provided
Woodburner Provided
BBQ
BBQ
Public transport travel
Public transport travel
23rd - 30th October  £1,008.70
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A spacious seaside retreat for couples in Swanage, just yards from the beach and stunning sea views on the Dorset coast.
Billet Doux
Swanage
5/5
2
1
1
1
Set on a quiet, private road in a peaceful part of Swanage, Billet Doux is a beautifully presented ground-floor retreat. It is ideal for couples or solo travellers looking to slow down and enjoy a more relaxed pace of life.
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
EV Charge Point
EV Charge Point
Ground Floor Bathroom
Ground Floor Bathroom
24th - 30th October  £840.69
23rd - 29th October  £840.69
+25 more stays
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Rosemary Cottage image
Rosemary Cottage
Dorchester
5/5
4
2
1
0
Rosemary Cottage is a welcoming 4-Star retreat set within a lively Dorset estate, perfect for families or friends. Sleeping four across two flexible bedrooms, this dog-friendly cottage blends antique character with modern comfort, opening directly onto the badminton lawn and
Hot Tub
Hot Tub
Allocated Parking
Allocated Parking
EV Charge Point
EV Charge Point
Near Supermarket
Near Supermarket
BBQ
BBQ
Bathroom Towels
Bathroom Towels
24th - 30th October  £975.50
26th - 30th October  £818.75
+18 more stays
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