Celebrate the arrival of early summer with a May half term break in Dorset. Our selection of holiday homes provides the perfect home base for exploring the county’s breathtaking landscapes, from the rolling hills of the countryside to the dramatic cliffs of the Jurassic Coast. Whether you’re seeking adventure or relaxation, Dorset has something for everyone, making it the ideal destination for your May half term holiday in the UK.
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,
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,
Save 15% on stays between 7th Oct 2025 - 4th Jan 2028
Allington Barn
Nr Blandford Forum
5/5
18
7
6
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Set quietly within the rolling countryside of North Dorset, Allington Barn is a place designed for gathering - where long tables fill with food and conversation, where mornings begin slowly with coffee on the terrace, and evenings stretch into laughter
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
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.
Bright third-floor apartment on Swanage's high street, moments from the beach with fantastic beach view. Lift access, with shops, cafés and the seafront right outside.
This traditional home embodies all the distinct qualities of a quintessential English country retreat in Dorset. This ‘chocolate box’ thatched cottage, located on a quiet country lane is surrounded by a beautiful garden.
1 Bedroom spacious holiday cottage near Corfe Castle. Nestled in the heart of the countryside within walking distance of Corfe Castle and the coast. Excellent quality detached accommodation which is highly recommended for walking and beach holidays.
Leap House is a well-presented three-bedroom semi-detached holiday retreat, sitting peacefully within a short walk of Wareham Quay. This well-presented holiday accommodation, is an excellent base to explore one of England’s Saxon Walled towns and nearby beaches of the Jurassic
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.
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
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Enjoy
May half term family holidays
Make the most of your time spent with your family with a stay in one of our well-appointed holiday cottages for May half term. Dorset offers a wealth of family-friendly activities. Sandy beaches and coastal walks to fascinating historical sites and charming market towns. Our cottages are designed with families in mind. They offer spacious living areas, comfortable bedrooms, and all the amenities you need for a stress-free holiday. Whether you’re planning a week-long stay or a shorter break, our May half term family-friendly cottages ensure everyone enjoys a memorable holiday.
Indulge in a
Luxury cottage for May half term
Add a touch of luxury to your May half term break by choosing one of our cottages with hot tubs. After a day spent exploring Dorset’s beautiful countryside, there’s nothing better than relaxing in the warm bubbles of a private hot tub. Our luxury cottages combine modern comforts with picturesque settings. They are the perfect choice for those who want to unwind and indulge during their holiday in May.
Pet-friendly
Self-catering for May half term
Our dog-friendly cottages for May half term welcome pets. They offer easy access to dog-friendly beaches, walking trails, and open spaces where your pets can roam freely. Most of the beaches in Dorset are still open to pets in May. So its the ideal time to plan your getaway.
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