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What's on in Dorset in May 2026

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What's on in Dorset in May

May is a wonderful time to enjoy Dorset, with longer days, blooming countryside and the coast looking its best. Spring is well and truly underway, bringing a relaxed atmosphere, outdoor events, local festivals and plenty of opportunities to explore the county’s towns, gardens and walking routes. With bank holidays and popular events throughout the month, booking ahead is recommended if you’re planning a spring break in Dorset.

What's on in may in dorset

Dorset Spring Show

Dates: 9th – 10th May

Dorset Spring Show is a lively May countryside event celebrating spring with farm animals, pony racing, craft demonstrations, food, flowers and family fun.

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What's on in may in dorset

Swanage Pirate Festival

Dates: 23rd & 24th May

Swanage Pirate Festival is a free, family-friendly weekend of pirate parades, cannon and sword displays, living history, sea shanties and beach battles.

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What's on in may in dorset

Dorchester Walking Festival

Date: 2nd – 10th May

Dorchester Walking Festival offers a week of guided and self-guided walks exploring Dorchester’s landscapes, history and countryside for all ages and abilities.

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What's on in may in dorset

Sunset Fish & Chips Cruise - Weymouth

Dates: 11th & 18th May

Weymouth’s Sunset Fish and Chips Cruise is a relaxing 3-hour golden-hour sail with Bennett’s fish and chips and scenic Jurassic Coast views.

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What's on in may in dorset

Bournemouth 7’s Festival

Dates: 22nd – 24th May

Bournemouth 7s Festival is a huge three-day sport and music event with competitions, live DJs, entertainment arenas and festival fun over the May Bank Holiday.

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What's on in may in dorset

May Half Term - Stories and Seedlings at Corfe Castle

Dates: 23rd – 31st May

Corfe Castle’s May Half Term – Stories and Seedlings offers family planting fun and interactive medieval storytelling tours bringing castle life to life.

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Keep Up to Date with Dorset

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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 2026/27!

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Find your perfect

May Half Term Cottage

Bluebell Cottage image
Bluebell Cottage
Dorchester
5/5
3
2
1
1
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,
Allocated Parking
Allocated Parking
Beach Under 5 Miles
Beach Under 5 Miles
Ground Floor Bathroom
Ground Floor Bathroom
Ground Floor Bedroom
Ground Floor Bedroom
Bathroom Towels
Bathroom Towels
Bed Linen Is Provided
Bed Linen Is Provided
4th - 6th June 2027  £805.00
30th May 2027 - 5th June 2027  £1,025.00
+33 more stays
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Pool and Tennis Court Access
Pool House image
Pool House
Minterne Magna
5/5
2
1
1
2
Romantic countryside escape for two with exclusive evening pool access, a wood burner and beautiful estate surroundings.
Swimming Pool
Swimming Pool
Allocated Parking
Allocated Parking
Woodburner Provided
Woodburner Provided
Ground Floor Bathroom
Ground Floor Bathroom
BBQ
BBQ
28th May 2027 - 4th June 2027  £1,075.00
29th May 2027 - 1st June 2027  £786.35
+42 more stays
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Leap House image
Leap House
Wareham
5/5
4
3
1
0
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
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Beach Under 5 Miles
Beach Under 5 Miles
Woodburner Provided
Woodburner Provided
Near Supermarket
Near Supermarket
28th May 2027 - 4th June 2027  £1,010.25
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Sea View
Penlu image
Penlu
Swanage
5/5
4
2
2
0
Central Swanage apartment sleeping four, just a short stroll from the beach, independent shops, cafés and the Jurassic Coast.
Sea Views
Sea Views
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Near Supermarket
Near Supermarket
Walk to Pub
Walk to Pub
1st - 6th June 2027  £839.35
3rd - 5th June 2027  £553.59
+33 more stays
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Hill View image
Hill View
Weymouth
4.9/5
4
2
1
1
Set in the peaceful Weymouth suburb of Preston, Hill View offers a delightful retreat for couples or small families.
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
5th - 6th June 2027  £627.92
2nd - 4th June 2027  £661.52
+42 more stays
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Primrose Cottage image
Primrose Cottage
Dorchester
5/5
2
1
1
1
Primrose Cottage is a romantic single-storey hideaway for two — dog-friendly and tucked within a tranquil Dorset estate. With a king-size bedroom and en-suite, a private enclosed garden, and woodland walks and estate amenities on the doorstep, it’s perfect for
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Beach Under 5 Miles
Beach Under 5 Miles
EV Charge Point
EV Charge Point
BBQ
BBQ
30th May 2027 - 4th June 2027  £960.65
31st May 2027 - 2nd June 2027  £688.40
+33 more stays
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Harbour Vista image
Harbour Vista
Weymouth
5/5
4
2
2
0
Set within a striking Grade II listed building on Weymouth’s historic harbour, Harbour Vista is a stylish third-floor apartment offering a front-row seat to one of Dorset’s most vibrant seaside towns.
Sea Views
Sea Views
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Near Supermarket
Near Supermarket
Public transport travel
Public transport travel
29th May 2027 - 5th June 2027  £1,181.75
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Ash Cottage image
Ash Cottage
Weymouth
5/5
2
1
1
1
Cosy single-storey retreat for two with vaulted ceilings, a log burner and sunny courtyard, perfect for romantic escapes.
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Woodburner Provided
Woodburner Provided
Ground Floor Bathroom
Ground Floor Bathroom
Ground Floor Bedroom
Ground Floor Bedroom
Coffee Machine
Coffee Machine
31st May 2027 - 3rd June 2027  £626.85
29th May 2027 - 5th June 2027  £1,497.65
+20 more stays
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Compass Cottage image
Compass Cottage
Swanage
4.8/5
4
2
1
1
A boutique, contemporary seaside cottage, nestled in the heart of the town centre of Swanage.
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Beach Under 5 Miles
Beach Under 5 Miles
Near Supermarket
Near Supermarket
Balcony
Balcony
3rd - 5th June 2027  £695.03
31st May 2027 - 3rd June 2027  £695.03
+33 more stays
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Lounge with Wood Burning Fire
Birch Cottage
Weymouth
5/5
4
2
1
2
A charming former stable conversion with two bedrooms, a wood burner and private courtyard, ideal for relaxed coastal stays.
Allocated Parking
Allocated Parking
Walk to places to eat
Walk to places to eat
Beach Under 5 Miles
Beach Under 5 Miles
Woodburner Provided
Woodburner Provided
Walk to Pub
Walk to Pub
Coffee Machine
Coffee Machine
1st - 6th June 2027  £1,497.50
28th May 2027 - 1st June 2027  £1,170.00
+20 more stays
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Westport Cottage image
Westport Cottage
Wareham
4.9/5
5
3
2
0
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.
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Beach Under 5 Miles
Beach Under 5 Miles
Woodburner Provided
Woodburner Provided
Near Supermarket
Near Supermarket
Public transport travel
Public transport travel
28th May 2027 - 4th June 2027  £1,193.50
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large holiday cottage near the jurassic coast
Coastguard Cottage
Worth Matravers
4.6/5
8
4
3
0
A lovely semi-detached cottage in the much sought after village of Worth Matravers, within walking distance of the Jurassic Coast.
Allocated Parking
Allocated Parking
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to places to eat
Walk to places to eat
Beach Under 5 Miles
Beach Under 5 Miles
Ground Floor Bathroom
Ground Floor Bathroom
BBQ
BBQ
28th May 2027 - 4th June 2027  £1,114.75
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Pets Go Free
Wind Chimes image
Wind Chimes
Swanage
5/5
4
2
1
2
Cosy dog-friendly cottage in Swanage with an enclosed garden, log burner and parking, just a short walk from the beach and town centre.
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to places to eat
Walk to places to eat
Beach Under 5 Miles
Beach Under 5 Miles
BBQ
BBQ
31st May 2027 - 2nd June 2027  £534.81
3rd - 6th June 2027  £543.23
+12 more stays
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Thistledown image
Thistledown
Dorchester
5/5
2
1
1
1
Thistledown is a light and inviting single-storey cottage, tucked within a peaceful Dorset estate and designed for couples seeking a romantic retreat. With a super king-size bedroom, private garden, and dog-friendly touches, it blends country charm with modern comfort. Estate
Allocated Parking
Allocated Parking
Beach Under 5 Miles
Beach Under 5 Miles
EV Charge Point
EV Charge Point
Ground Floor Bathroom
Ground Floor Bathroom
Ground Floor Bedroom
Ground Floor Bedroom
BBQ
BBQ
28th May 2027 - 5th June 2027  £1,244.57
1st - 4th June 2027  £742.85
+33 more stays
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Oak Cottage image
Oak Cottage
Weymouth
5/5
4
2
1
2
Characterful two-bedroom cottage with a secluded courtyard garden and beautiful bathroom, close to Dorset's top attractions.
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Woodburner Provided
Woodburner Provided
Walk to Pub
Walk to Pub
28th May 2027 - 3rd June 2027  £1,722.50
28th May 2027 - 1st June 2027  £1,125.00
+20 more stays
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Ailwood Cottage couples holiday cottage for walking holidays in Purbeck Dorset
Ailwood Cottage
Nr Corfe Castle
4.8/5
2
1
1
2
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.
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Beach Under 5 Miles
Beach Under 5 Miles
Ground Floor Bathroom
Ground Floor Bathroom
Ground Floor Bedroom
Ground Floor Bedroom
Bathroom Towels
Bathroom Towels
29th May 2027 - 5th June 2027  £764.25
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The Dairy image
Beech Cottage
Osmington
5/5
2
1
1
0
Peaceful one-bedroom cottage for two, offering a king-size bed, wood burner and south-facing courtyard garden.
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to the beach
Walk to the beach
Walk to places to eat
Walk to places to eat
Woodburner Provided
Woodburner Provided
28th May 2027 - 1st June 2027  £899.08
28th May 2027 - 2nd June 2027  £1,158.85
+20 more stays
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Historic Country Estate
Kings House image
Kings House
Minterne Magna
5/5
4
2
1
2
A stylish village retreat with a secure garden, open fire and access to Minterne Estate's pool, tennis court and gardens.
Swimming Pool
Swimming Pool
Allocated Parking
Allocated Parking
Secure Garden (pets)
Secure Garden (pets)
Secure Garden (Toddlers)
Secure Garden (Toddlers)
Walk to places to eat
Walk to places to eat
Woodburner Provided
Woodburner Provided
28th May 2027 - 5th June 2027  £2,212.00
28th May 2027 - 6th June 2027  £2,259.80
+3 more stays
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Owl Cottage image
Owl Cottage
Wareham
4.9/5
4
2
1
1
A quaint stone cottage in the heart of Wareham. Beautifully decorated throughout.
Walk to places to eat
Walk to places to eat
Town Centre
Town Centre
Beach Under 5 Miles
Beach Under 5 Miles
Near Supermarket
Near Supermarket
Public transport travel
Public transport travel
Walk to Pub
Walk to Pub
28th May 2027 - 4th June 2027  £1,136.50
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Forget Me Not Cottage image
Forget Me Not Cottage
Dorchester
4.8/5
4
2
1
0
Forget Me Not Cottage is a cosy 4-Star retreat set within a peaceful Dorset estate, perfect for couples or families. Sleeping four, this dog-friendly two-storey cottage features comfortable interiors, flexible bedrooms, and French doors opening onto the shared gardens and
Hot Tub
Hot Tub
Allocated Parking
Allocated Parking
EV Charge Point
EV Charge Point
Near Supermarket
Near Supermarket
BBQ
BBQ
Bathroom Towels
Bathroom Towels
31st May 2027 - 5th June 2027  £1,311.28
2nd - 5th June 2027  £1,161.12
+33 more stays
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