beautiful dorset landscape to be enjoyed on a dorset holiday
Discover

What's on in Dorset in May 2025

Keep Up to Date with Dorset

Subscribe to our Newsletter

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!

Find your perfect

May Half Term Cottage

Save 10% on stays before 8th March
Winspit View image
Winspit View
Worth Matravers
4.8/5
3 Bedrooms. The bungalow is located on the edge of the village of Worth Matravers, in a rural idyll with fantastic views across open farmland to Winspit and the sea. A lovely holiday cottage to rent in Worth Matravers, an exclusive village in Dorset.
6
3
2
1
Holiday prices from  £682
View & Book
Save 10% on stays before 22nd March
Ridgeview Cottage image
Ridgeview Cottage
Corfe Castle
4.6/5
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
Holiday prices from  £475
View & Book
Save 25% on stays between 1st Nov - 19th Dec
+2 more discounts
Orchid House image
Orchid House
Langton Matravers
4.9/5
A delightful big cottage in Purbeck, set right on the doorstep of Dorset’s most breath-taking coastal walks, in the village of Langton Matravers.
8
4
3
2
Holiday prices from  £652
View & Book
Save 20% on stays before 8th March
Save 15% on stays before 22nd March
1 Westport Cottage Ph3 Web
Westport Cottage
Wareham
4.9/5
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.
5
3
2
0
Holiday prices from  £446
View & Book
Old Stone House
Swanage
4.8/5
If you want to stay in well proportioned, historic cottage by the sea - The Old Stone has to be at the top of your list.
7
3
2
2
Holiday prices from  £377
View & Book
Save 10% on stays before 22nd March
3 Puddledock Cottage image
3 Puddledock Cottage
Sutton Poyntz, Nr Weymouth
5/5
Enjoy soaking up the Dorset sunshine in this newly renovated countryside cottage, tucked away in the quiet village of Sutton Poyntz.
6
3
1
0
Holiday prices from  £431
View & Book
Save 20% on stays before 22nd March
Wye Knot image
Wye Knot
Swanage
4.8/5
A delightful ground floor apartment with private garden is perfectly placed for a family's getaway, within easy access to Swanage beach and town attractions.
4
2
2
1
Contact us for prices
View & Book
Save 20% on stays before 22nd March
Froxfield Cottage image
Froxfield Cottage
Langton Matravers
4.9/5
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.
6
3
2
1
Holiday prices from  £481
View & Book
Save 10% on stays before 22nd March
Coastguard Cottage image
Coastguard Cottage
Worth Matravers
4.6/5
A lovely semi-detached cottage in the much sought after village of Worth Matravers, within walking distance of the Jurassic Coast.
8
4
3
0
Holiday prices from  £509
View & Book
Save 10% on stays before 22nd March
Save 10% on stays between 14th - 22nd Feb
Lulwind image
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
Holiday prices from  £639
View & Book
Save 20% on stays before 22nd March
Cheesemans Cottage Perfect Country Retreat In The Dorset Countryside External 2
Cheesemans Cottage
Muckleford, Dorchester
4.6/5
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.
5
2
1
3
Contact us for prices
View & Book
Save 15% on stays before 22nd March
Forest Edge image
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
Holiday prices from  £364
View & Book
Sea Tower
Weymouth
0/5
Breathtaking luxury holiday home which is yards from Weymouth beach. Sea Tower has wide ranging coastal views and an exquisite interior for a luxury break.
6
3
2
0
Holiday prices from  £742
View & Book
Save 20% on stays before 8th March
Save 10% on stays before 22nd March
Purbeck Cottage (Kings) image
Purbeck Cottage (Kings)
Swanage
4.7/5
3 bedroom family home with two parking spaces and large covered patio to enjoy outside dining whatever the weather.
6
3
1
0
Holiday prices from  £376
View & Book
Save 15% on stays before 22nd March
Canaan image
Canaan
Worth Matravers
4.9/5
4 bedrooms. A wonderful architecturally designed, large family holiday home in Worth Matravers. Completed to the highest standard and incorporating a sumptuous interior. It’s open plan design, galleried first floor landing and very large kitchen makes this the ideal choice for the extended family, walkers and those of you who wish to relax in this stylish property set in the heart of the English coastal countryside.
8
4
3
2
Holiday prices from  £834
View & Book
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
Holiday prices from  £339
View & Book
Save 10% on stays between 4th - 25th Apr
Bronte Cottage image
Bronte Cottage
Wareham
4.8/5
3 Bedrooms. Bronte Cottage is a charming holiday cottage in Wareham, hidden away in a fabulous location a few strides from Wareham Quay and the river Frome.
4
3
2
1
Holiday prices from  £449
View & Book
Save 20% on stays before 1st March
Save 15% on stays before 22nd March
Sea reach external
Sea Reach
Swanage
4.9/5
2 Bedrooms. We are delighted to introduce Sea Reach, this spacious and modern ground floor apartment is in a prime place to stay in Swanage, just 3/4 minutes’ walk from the beach.
4
2
1
0
Holiday prices from  £429
View & Book
Save 10% on stays before 22nd March
Greenhayes image
Greenhayes
Langton Matravers
4.8/5
Lovely, traditional cottage with stunning country views to the coast. Ideal for a romantic getaway or for small families. Pet friendly.
4
2
1
2
Holiday prices from  £508
View & Book
Save 20% on stays before 22nd March
+4 more discounts
Littlecot image
Littlecot
Weymouth
5/5
A gorgeous, detached family home within stones throw of Smallmouth Bay and the Rodwell trail. Ideal for those who want a comfy base for friends or extended family.
8
4
2
2
Holiday prices from  £550
View & Book