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What's on in Dorset in May 2025

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As we wrap up an exciting May in Dorset, with its sunny bank holidays, blooming countryside, and lively festivals, we’d like to thank everyone who joined in the fun! While this year’s calendar is coming to a close, we’re already gearing up for an even more thrilling 2025. Stay tuned for next year’s itinerary of must-see events and special offers. Do you want to keep up-to-date with what’s on in May in Dorset this year and the next? Our email newsletter will keep you up-to-date with the ins and outs of our lovely coastal county, including upcoming events, our favourite attractions and landmarks, and our latest accommodation offers. Sign up today and be the first to hear about what’s happening in 2025!

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Find your perfect

May Half Term Cottage

Heathlands image
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.
6
3
1
0
24th - 31st May 2025  £1,422.40
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Daisy’s
Swanage
4.7/5
Stylishly decorated 3 bedroom holiday home in Swanage. Daisy's offers everything you need for a relaxing break, from comfortable bedrooms with ensuite for each room to a private bubbling hot tub, perfect for unwinding after a long day exploring the coast!
6
3
3
1
24th - 31st May 2025  £1,303.75
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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.
6
3
2
0
24th - 31st May 2025  £1,303.75
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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.
5
3
2
2
24th - 31st May 2025  £1,589.35
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Angel Cottage
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
2
1
1
2
24th - 31st May 2025  £724.65
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2018 Front PHOTO
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.
6
3
2
0
24th - 31st May 2025  £1,302.70
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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.
2
1
1
0
24th - 31st May 2025  £589.75
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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.
3
2
1
2
25th - 28th May 2025  £775.95
26th - 29th May 2025  £775.95
24th - 28th May 2025  £887.60
+18 more stays
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Ridgeview Cottage image
Ridgeview Cottage
Corfe Castle
4.5/5
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.
6
3
2
0
24th - 31st May 2025  £1,198.75
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Dream Cottage
Portland
5/5
A stylish, compact cottage - ideal for friends and small families to get together to enjoy the coast, walking and watersports.
6
3
2
0
30th - 31st May 2025  £498.60
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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.
4
2
2
2
24th - 31st May 2025  £761.95
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Flat 3 4 Cranborne Rd Ph2 Web
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.
4
2
1
0
24th - 31st May 2025  £842.80
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