October Half Term Cottages in Dorset
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October Half Term Holiday Cottages

As autumn settles over Dorset, the countryside comes alive with a stunning palette of gold, amber, and crimson, and the gentle rustle of fallen leaves beneath your feet and the crisp air mark the arrival of the October half term. This is the perfect time to explore Dorset’s rugged coast and countryside, with fewer crowds and a peaceful scene that makes for a truly memorable getaway. Whether you’re seeking October half term breaks in the UK for the whole family or a quiet retreat, our selection of holiday cottages for October half term offers something for everyone.

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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
1 night fromNone available
3 nights from £668.75
7 nights fromNone available
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Owls Roost
Ringstead Bay
5/5
2
1
1
0
Luxury couples' retreat near Ringstead Bay with a super-king bedroom, freestanding bath, peaceful estate gardens and Jurassic Coast walks nearby.
Allocated Parking
Allocated Parking
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
BBQ
BBQ
Walk to Pub
Walk to Pub
Coffee Machine
Coffee Machine
1 night from £443.20
3 nights from £614.88
7 nights from £887.50
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Save 12% on stays before 11th November
Stone Quay Cottage
Swanage
4.9/5
3
2
1
2
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
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Near Supermarket
Near Supermarket
Public transport travel
Public transport travel
Walk to Pub
Walk to Pub
1 night fromNone available
3 nights from £510.76
7 nights fromNone available
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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
1 night from £575.46
3 nights from £663.87
7 nights from £929.10
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Save 10% on stays before 24th October
Malvern Apartment
Swanage
4.5/5
2
1
1
0
A spacious Edwardian apartment for two, just a short walk from Swanage Beach, with period charm and a glimpse of the bay.
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
1 night fromNone available
3 nights from £360.76
7 nights from £499.25
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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
1 night from £362.86
3 nights from £387.69
7 nights from £556.65
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Sea Breeze
Swanage
5/5
4
2
2
0
Tucked away in the centre of Swanage, Sea Breeze is a bright and welcoming second-floor apartment just a short stroll from the beach, shops, and restaurants. With two bedrooms, two bathrooms, and all the comforts of home, this well-located flat
Allocated Parking
Allocated Parking
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Near Supermarket
Near Supermarket
Public transport travel
Public transport travel
Walk to Pub
Walk to Pub
1 night from £297.00
3 nights fromNone available
7 nights from £911.25
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Abbeydale
Wool
5/5
5
3
2
2
A gorgeous family home just 5 miles from Luworth Cove and Durdle Door.
Beach Under 5 Miles
Beach Under 5 Miles
BBQ
BBQ
Walk to Pub
Walk to Pub
Bathroom Towels
Bathroom Towels
Bed Linen Is Provided
Bed Linen Is Provided
1 night from £529.34
3 nights fromNone available
7 nights fromNone available
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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
1 night fromNone available
3 nights from £642.75
7 nights from £970.00
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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
1 night fromNone available
3 nights from £848.33
7 nights fromNone available
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Underhill
Nr Corfe Castle
5/5
7
4
3
3
Tucked away on a quiet lane just a short drive from Corfe Castle, Underhill offers the rare combination of seclusion, space, and true dog-friendliness near one of Dorset’s most iconic villages. Set entirely on one level and surrounded by greenery,
Allocated Parking
Allocated Parking
Beach Under 5 Miles
Beach Under 5 Miles
Woodburner Provided
Woodburner Provided
Wheelchair Friendly
Wheelchair Friendly
Ground Floor Bathroom
Ground Floor Bathroom
Ground Floor Bedroom
Ground Floor Bedroom
1 night fromNone available
3 nights fromNone available
7 nights from £1,865.00
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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
1 night fromNone available
3 nights from £571.25
7 nights from £860.00
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Newton House
Swanage
4.6/5
6
3
2
0
A spacious family home with 3 bedrooms just a 10-minute walk from Swanage Beach, with a secluded garden, balcony and room for everyone to unwind.
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
Near Supermarket
Near Supermarket
Balcony
Balcony
1 night fromNone available
3 nights fromNone available
7 nights from £936.25
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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
1 night fromNone available
3 nights fromNone available
7 nights from £639.60
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Bluebell Cottage
Dorchester
5/5
3
2
1
1
Bluebell Cottage is a bright and welcoming ground-floor retreat, set within the courtyard of a peaceful Dorset estate. Perfect for a couple or small family, it offers two bedrooms, a cosy open-plan living space, and dog-friendly touches. With landscaped gardens,
Allocated Parking
Allocated Parking
Beach Under 5 Miles
Beach Under 5 Miles
Ground Floor Bathroom
Ground Floor Bathroom
Ground Floor Bedroom
Ground Floor Bedroom
Bathroom Towels
Bathroom Towels
Bed Linen Is Provided
Bed Linen Is Provided
1 night fromNone available
3 nights from £587.50
7 nights from £885.00
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Seaspray
Swanage
5/5
5
3
2
0
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
Sea Views
Sea Views
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Balcony
Balcony
Public transport travel
Public transport travel
1 night from £617.80
3 nights fromNone available
7 nights from £1,047.55
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Brook Cottage
Corfe Castle
4.8/5
6
3
3
0
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
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Ground Floor Bathroom
Ground Floor Bathroom
BBQ
BBQ
Public transport travel
Public transport travel
Walk to Pub
Walk to Pub
2 nights from £937.24
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Thistledown
Dorchester
5/5
2
1
1
1
Thistledown is a light and inviting single-storey cottage, tucked within a peaceful Dorset estate and designed for couples seeking a romantic retreat. With a super king-size bedroom, private garden, and dog-friendly touches, it blends country charm with modern comfort. Estate
Allocated Parking
Allocated Parking
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
BBQ
BBQ
1 night fromNone available
3 nights from £571.25
7 nights from £825.00
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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
1 night from £470.92
3 nights fromNone available
7 nights from £1,135.75
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Historic Country Estate
Kings House
Minterne Magna
5/5
4
2
1
2
A stylish village retreat with a secure garden, open fire and access to Minterne Estate's pool, tennis court and gardens.
Swimming Pool
Swimming Pool
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to places to eat
Walk to places to eat
Woodburner Provided
Woodburner Provided
1 night from £632.00
3 nights from £1,002.25
7 nights from £1,315.71
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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
1 night fromNone available
3 nights fromNone available
7 nights from £1,162.00
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Save 30% on stays before 24th October
Bucknowle Lodge
Church Knowle
4.8/5
8
4
3
2
Beautiful, spacious Dorset lodge for large parties. Within walking distance of Corfe Castle and a short drive to the coast.
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to places to eat
Walk to places to eat
Beach Under 5 Miles
Beach Under 5 Miles
Woodburner Provided
Woodburner Provided
1 night fromNone available
3 nights from £815.00
7 nights fromNone available
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The Lookout
Silverlake
5/5
10
4
4
0
An exceptional and unique luxury lakeside home. Thoughtfully designed with style, comfort, and indulgence in mind, The Lookout is a modern lakeside home set within the award-winning Silverlake Estate near Dorchester. Every element of this contemporary four-bedroom property has been
Hot Tub
Hot Tub
Swimming Pool
Swimming Pool
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Woodburner Provided
Woodburner Provided
EV Charge Point
EV Charge Point
1 night from £1,839.12
3 nights fromNone available
7 nights fromNone available
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Wisteria Cottage
Dorchester
5/5
4
2
1
0
Wisteria Cottage is a welcoming 4-Star retreat set within a peaceful Dorset estate, overlooking the courtyard pond at the front and gardens at the back. Sleeping four, this dog-friendly two-storey cottage offers a light modern interior, flexible bedrooms, and French
Hot Tub
Hot Tub
Allocated Parking
Allocated Parking
EV Charge Point
EV Charge Point
Near Supermarket
Near Supermarket
BBQ
BBQ
Bathroom Towels
Bathroom Towels
1 night fromNone available
3 nights fromNone available
7 nights from £1,000.00
View & Book
Explore our

October Half-Term Family Holidays

Dorset is an ideal destination for a family holiday during October half term, offering a variety of activities that cater to all ages. Picture the kids collecting conkers in the woodlands or running through piles of leaves in the park. Visit one of the many local attractions, from historic Corfe Castle to interactive fossil museums, where the whole family can learn and have fun together. Our October half term cottages in Dorset provide the perfect base for your adventures, with many located close to family-friendly spots.

In the evenings, retreat to one of our holiday cottages with woodburners, where you can unwind by the fire with a cup of hot chocolate. Our self-catering cottages for October half term are fully equipped to make your stay as comfortable as possible, and our large cottages have plenty of space for the whole family to relax after a day of exploring.

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Dog-Friendly Cottages for October Half-Term

No family holiday is complete without your four-legged friend, and Dorset is a paradise for dogs in autumn. With our Dorset dog-friendly cottages, your pets can enjoy a holiday as much as you. Imagine long walks along the coast path, where your dog can roam freely and enjoy the fresh sea air. Many of our October half term cottages are also close to the beach, which are all open for dogs from the end of September, and expansive countryside trails, offering endless opportunities for adventures in nature.

After a day of exploration, return to your welcoming self-catering cottage, where both you and your dog can relax in comfort. These dog-friendly holiday cottages often feature enclosed gardens, for your peace of mind while you’re away.

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Escape to the Countryside

For those who prefer the tranquillity of rural settings, our cottages to rent for October half term are nestled in some of Dorset’s most picturesque landscapes. Here, you can enjoy the slower pace of life, with scenic walks through the countryside, visits to quaint villages, and afternoons spent in cosy tearooms sampling local delicacies. Whether you’re planning a serene escape in a romantic cottage or a family trip, our October half term holiday cottages offer a perfect retreat from the hustle and bustle of everyday life.

Whether you’re looking for family-friendly accommodation or a quiet Dorset country cottage, we have the perfect self-catering holiday for October half term. And if you’re seeking inspiration for family activities during the half-term holiday, explore our local expert guide on the best things to do in Dorset in October.