Whether you’re planning a summer holiday on the Jurassic Coast, a cosy winter retreat, or a special family gathering, our Dorset holiday cottages for 2027 are now available to book.
From beachfront apartments overlooking Swanage Bay to countryside cottages surrounded by rolling hills, our collection offers something for every type of holiday. Choose from dog-friendly cottages, luxury homes with hot tubs, large properties for group celebrations, and romantic retreats perfect for couples.
Booking early for 2027 gives you the widest choice of properties and dates, particularly during school holidays, bank holiday weekends, and the peak summer season. Many of our most popular cottages are reserved well in advance by returning guests who know just how special a Dorset holiday can be.
As a local, family-run business, we’re passionate about helping guests discover the very best of Dorset. Every cottage in our collection has been personally selected for its character, comfort, and location. Whether you’re looking for a peaceful countryside hideaway or a cottage within walking distance of the beach, our experienced team can help you find the perfect match.
Browse our Dorset holiday cottages below and start planning your 2027 getaway today.
Swanage
5/5
Langton Matravers
4.9/5
Swanage
4.8/5
Dorchester
4.9/5
Swanage
4.9/5
Swanage
4.8/5
Wareham
5/5
Weymouth
5/5
Lulworth Cove,
5/5
Weymouth
4.8/5
Swanage
5/5
Minterne Magna
5/5
Worth Matravers
4.6/5
Charlton Marshall, Nr Blandford
4.8/5
Minterne Magna
5/5
Swanage
4.9/5
Langton Matravers
4.8/5
Corfe Castle
5/5
Dorchester
5/5
Swanage
5/5
Dorchester
4.8/5
Dorchester
5/5
Swanage
4.8/5
Weymouth
4.9/5
Dorchester
5/5
Langton Matravers
4.9/5
Swanage
5/5
Swanage
4.9/5
Sandford
4.8/5
Dorchester
5/5
Ringstead Bay
5/5
Weymouth
5/5
Dorchester
5/5
Swanage
4.8/5
Dorchester
5/5
Wareham
5/5
Corfe Castle
4.8/5
Swanage
5/5
Dorchester
5/5
Corfe Castle
5/5
A cottage holiday in Dorset offers the perfect opportunity to slow down, explore, and reconnect with nature. With over 95 miles of spectacular coastline, charming villages, rolling countryside and historic landmarks, Dorset is a destination that rewards every type of traveller.
The county is home to the world-famous Jurassic Coast, England’s only natural UNESCO World Heritage Site, where dramatic cliffs, hidden coves and fossil-rich beaches create some of the country’s most breathtaking scenery. Beyond the coast, you’ll discover ancient castles, traditional market towns, picturesque harbours and miles of walking and cycling routes waiting to be explored.
Dorset is equally appealing throughout the seasons. Summer brings beach days and coastal adventures, spring fills the countryside with colour, autumn offers quieter walking trails and cosy pub lunches, while winter provides the perfect backdrop for peaceful escapes and festive breaks.
Whether you’re looking for a romantic retreat, a family holiday by the sea, a dog-friendly adventure or a large gathering with friends, Dorset offers something for everyone. From coastal cottages with sea views to countryside hideaways with hot tubs, our collection of Dorset holiday cottages for 2027 provides the perfect base from which to discover this remarkable county.
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