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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.

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Beach Approach
Swanage
4.8/5
Settle into a lovely family holiday at Beach Approach. A two bedroom ground floor apartment. A flat walk will take you to Swanage beach and High Street, which is lined with cute cafés, boutiques, and fine restaurants. Beach Approach is perfect for families with top sights in easy reach: Swanage Railway is just a two minute stroll away; take a trip down memory lane on the vintage steam engine to the historic village of Corfe Castle.
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24th - 31st May 2025  £842.80
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Ridgeview Cottage
Corfe Castle
4.7/5
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.
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24th - 31st May 2025  £1,198.75
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Forest Edge
Sandford
4.8/5
Forest Edge is a two bedroom semi-detached chalet bungalow offering luxury accommodation near Wareham. Mainly laid out on the ground floor, this delightful holiday home has been completely refurbished to a very high standard.
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24th - 31st May 2025  £761.95
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Newton House
Swanage
4.6/5
3 bedrooms. The owners of this spacious seaside home, which is very close to Swanage beach have stylishly furnished with a contemporary and comfortable interior.
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24th - 31st May 2025  £1,303.75
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Seacombe
Langton Matravers
4.9/5
Nestled in the sleepy village of Langton Matravers proudly stands Seacombe, an exquisite 4 bedroom family home. This stunning link detached home could easily be the set to a photoshoot for Country Living magazine. Furnished with high quality new furniture, sumptuous duck down quilts, crisp white linen and beds so comfortable you will struggle to leave them, Seacombe is the holiday home you've been searching for. ?
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24th - 31st May 2025  £1,924.30
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Stone Quay Cottage
Swanage
4.9/5
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 cottage dates back to the 1850’s but has been completely renovated to provide a beautiful modern home.
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25th - 28th May 2025  £775.95
25th - 27th May 2025  £775.95
28th - 30th May 2025  £775.95
+18 more stays
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Cricket Cottage
Swanage
4.7/5
1 Bedroom. This quaint seaside cottage is the perfect destination for two to enjoy a romantic getaway in the heart of Swanage. Just a 20-minute meander from the main beach, sparkling clear Swanage shores, shops, restaurants and attractions. Space is plentiful in this deceptively generous cottage.
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24th - 31st May 2025  £611.25
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Angel Cottage
Swanage
4.7/5
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 heritage coastline or relax and unwind on the blue flag sandy beach
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24th - 31st May 2025  £724.65
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Malvern Apartment
Swanage
4.5/5
This appealing large, ground floor apartment is part of a modern conversion of a former Edwardian hotel, right in the heart of the seaside town of Swanage in a quiet residential, tree lined street, less than 5 mins walk to restaurants, pubs, shops and the beach. You can enjoy a lovely glimpse view across Swanage bay from the lounge bay window.
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24th - 31st May 2025  £589.75
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Newton Manor Grange
Swanage
4.6/5
3 bedrooms. This beautiful four star holiday home is the ideal choice for a self catering holiday in Swanage. This home boasts large picture windows and is an unusual upside down house that takes full advantage of the views, across the seaside town of Swanage to the sea and the Isle of White beyond. WIFI.
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24th - 31st May 2025  £1,302.70
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Lulwind
Lulworth Cove
4.8/5
3 bedrooms. Lulwind, a comfortable and pretty modern semi-detached thatched cottage, particularly suitable for families is set in the heart of this beautiful village, with views of the South West Coast path and only a two minute walk from Lulworth Cove. An excellent choice for a self catering cottage in Lulworth Cove.
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24th - 31st May 2025  £1,589.35
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Heathlands
Studland
4.6/5
3 bedrooms. Heathlands is a modern cottage, the ideal base for family holidays in Studland. This light and airy holiday home is a short walk from Studlands long sandy beach.
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1
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24th - 31st May 2025  £1,422.40
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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, from sandy beaches and coastal walks to fascinating historical sites and charming market towns. Our cottages are designed with families in mind, offering 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, making them 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, offering easy access to dog-friendly beaches, walking trails, and open spaces where your pets can roam freely. For those who prefer the flexibility of cooking their own meals, our self-catering May half term cottages are fully equipped with modern kitchens, allowing you to enjoy home-cooked meals at your convenience. Whether you’re planning a relaxing getaway or an adventure-packed holiday, our self-catering holidays provide the perfect base for a unique experience in Dorset.