Your search returned 351 cottages.
REFINE SEARCH-
- Sleeps2
- Bedrooms1
- Pet FriendlyNo
123 On The Sea – Victoria’s Place is a beautifully appointed seafront apartment in Weymouth, Dorset, featuring beach views, private parking, and a bright open-plan layout. (Ref. 1133962)
- Wi-fi
- Off-road parking
- Dishwasher
- Baby-friendly
3 nights from Wed 28th Oct From £571
-
- Sleeps2
- Bedrooms1
- Pet FriendlyNo
123 On The Sea - The Eaves is a charming apartment overlooking the beach in Weymouth, Dorset, boasting off-road parking and ample nearby attractions. (Ref. 1133964)
- Wi-fi
- Off-road parking
- Dishwasher
- Baby-friendly
3 nights from Mon 26th Oct From £442
-
- Sleeps10
- Bedrooms5
- Pet FriendlyYes
Harbins Farm is a farmhouse dating back 200 years, in Glanvilles Wootton Near Sherborne, Dorset, pet-friendly with woodburning stoves. (Ref. 1200098)
- Pets go free
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
3 nights from Fri 30th Oct
was £1182From £1046 -
- Sleeps4
- Bedrooms2
- Pet FriendlyYes
2 North Road is a welcoming, detached bungalow situated in Maiden Newton, Dorset, with gardens, off-road parking, and close by countryside. (Ref. 1200259)
- Pets go free
- Wi-fi
- Off-road parking
- Electric car charging
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Sun 25th Oct From £454
-
- Sleeps4
- Bedrooms2
- Pet FriendlyNo
Swanny View is a welcoming caravan featuring open‑plan living, enclosed decking with furniture, EV charging on‑site and easy access to local amenities. (Ref. 1201196)
- Wi-fi
- Off-road parking
- Ground floor bedroom
3 nights from Sun 25th Oct From £407
Book nowLast booked 7 hours ago -
- Sleeps5
- Bedrooms3
- Pet FriendlyNo
Cove Cottage is a well-located cottage in Weymouth, Dorset, boasting close proximity to the beach and easy access to local shops and nearby amenities. (Ref. 1094256)
- Wi-fi
- Off-road parking
- Washing machine
3 nights from Sat 24th Oct From £674
-
- Sleeps4
- Bedrooms2
- Pet FriendlyNo
Beck House, a welcoming mews house within a secure gated development in the heart of Weymouth, just a short walk from the harbour, beach and amenities. (Ref. 1201741)
- Wi-fi
- Dishwasher
- Washing machine
3 nights from Sat 24th Oct From £492
-
- Sleeps4
- Bedrooms2
- Pet FriendlyNo
A detached barn conversion set within the village of Long Bredy. (Ref. 998739)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Sat 24th Oct From £787
-
- Sleeps6
- Bedrooms3
- Pet FriendlyNo
Rose Cottage, a charming thatched cottage nestled in Osmington, within Dorset National Landscape, boasts a large garden and proximity to local amenities. (Ref. 1200211)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
3 nights from Sat 24th Oct From £718
-
- Sleeps2
- Bedrooms1
- Pet FriendlyNo
The Shippon is a spacious and inviting home, with characterful yet chic features, perfect for a couples retreat at Lower Lye, in the Blackdown Hills AONB. (Ref. 1087064)
- Wi-fi
- Electric car charging
- Ground floor bedroom
- Hot Tub
- Dishwasher
- Washing machine
- Baby-friendly
-
5% off - Mon 26th Oct to 2nd Nov 2026
3 nights from Mon 26th Oct
was £514From £502Book nowLast booked 8 hours ago
Take advantage of our hand-picked cottages for October Half-Term to experience Dorset's stunning fall beauty. Discover inviting cottages amidst gorgeous seaside scenery and golden landscapes, ideal for making enduring family memories.
Why a Holiday Cottages For October Half-Term
Choosing vacation rentals in Dorset for October Half-Term provides a charming getaway to a location immersed in seasonal splendour. The natural beauty of Dorset is enhanced by the changing colours of the leaves and the crispness of the air.
This is the best time of year for families to experience the gorgeous Jurassic Coast, mediaeval villages, and dynamic towns because of the season's charm and lack of tourists.
After a day of touring historic castles like Corfe Castle or strolling along Lyme Regis' fossil-rich beaches, picture yourself spending the nights by a roaring fire while drinking hot chocolate. The many outdoor pursuits available in Dorset, such as beautiful treks and animal viewing, are ideal for a family holiday.
Additionally, the regional cuisine will warm your soul, from hearty pub grub to freshly caught fish. When you choose Dorset vacation rentals for October Half-Term, you'll be immersed in a verdant beauty where you may make priceless memories with your loved ones.
Places to Visit in and Around your October Holiday Cottage
Your October Half-Term vacation in Dorset is sure to be filled with enthralling places to discover. The Jurassic Coast's calm charm and beautiful cliffs are what make West Bay, a coastal jewel, so special.
With its extensive fossil history and recognisable Cobb Harbour, Lyme Regis beckons. Here, you may spend hours beachcombing and admiring the coastal scenery. For a lively waterfront experience that includes leisurely boat excursions, charming quayside shops, and delectable seafood, head to Poole.
The historic ruins of Corfe Castle provide breath-taking panoramic views while affording a window into the past. Sand beaches, a historic pier, and a picturesque railway may be found in the Victorian seaside town of Swanage. The sandy beaches and active harbour in Weymouth also offer plenty of chances for watersports and beach recreation.
Your October Half-Term vacation will be packed with treasured memories and wonderful experiences thanks to Dorset's many charming towns and villages, each of which has its own special charm and attractions.
Types of Self-Catering Homes for October Half-Term
At Dream Cottages, there are a wide selection of holiday homes to reside in this Autumn. Treat yourself to some extra splendour with a luxury cottage or a cottage with a hot tub. You can also browse this collection of romantic cottages, February half term cottages, May half term cottages or this collection of cottages for New Years Eve for an escape you’re sure to remember.
For an unforgettable escape to the South Coast this Autumn, choose a holiday cottage for October half-term in Dorset. Book your cosy holiday home with Dream Cottages today.