Your search returned 345 cottages.
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- Sleeps6
- Bedrooms3
- PetsNo
A beautifully presented property resting in the pretty village of Burton Bradstock. (Ref. 1069147)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
3 nights from Fri 29th May £1072
Book nowLast booked yesterday -
- Sleeps4
- Bedrooms2
- PetsNo
A beautifully furnished annexe cottage on the edge of the little hamlet of Hazelbury Bryan in Dorset. (Ref. 969185)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
3 nights from Wed 27th May £391
Book nowLast booked yesterday -
- Sleeps4
- Bedrooms2
- PetsNo
The Hayloft is a versatile, characterful, quirky, and Grade II-listed home, perfect for families or friends at Lower Lye, in the Blackdown Hills AONB. (Ref. 1120037)
- Wi-fi
- Electric car charging
- Ground floor bedroom
- Hot Tub
- Dishwasher
- Washing machine
- Baby-friendly
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20% off - Fri 27th Mar to 3rd Apr 2026
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10% off - Mon 13th Apr to 20th Apr 2026
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5% off - Mon 20th Apr to 27th Apr 2026
3 nights from Mon 1st Jun £682
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- Sleeps2
- Bedrooms1
- PetsNo
The Shippon is a spacious and inviting home, with characterful yet chic features, perfect for a couples retreat at Lower Lye, in the Blackdown Hills AONB. (Ref. 1087064)
- Wi-fi
- Electric car charging
- Ground floor bedroom
- Hot Tub
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Mon 25th May £910
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- Sleeps8
- Bedrooms4
- PetsYes
Unwind in this stylish countryside retreat with a private, screened hot tub, cosy woodburner, pool table and spacious enclosed garden. (Ref. 1070465)
- Wi-fi
- Off-road parking
- Hot Tub
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Mon 1st Jun £1050
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- Sleeps2
- Bedrooms1
- PetsNo
This attractive, one-bedroom cottage resides in Uploders near Bridport, Dorset. (Ref. 1117867)
- Wi-fi
- Off-road parking
- Washing machine
3 nights from Mon 1st Jun £402
Book nowLast booked 2 days ago -
- Sleeps4
- Bedrooms2
- PetsNo
A well-presented barn conversion resting on the outskirts of Okeford Fitzpaine, Dorset. (Ref. 1137516)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
3 nights from Sun 31st May £584
Book nowLast booked yesterday -
- Sleeps4
- Bedrooms2
- PetsNo
A stylish property resting in the resort of Weymouth, Dorset. (Ref. 1100742)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Fri 22nd May £788
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- Sleeps6
- Bedrooms3
- PetsYes
An exceptional detached property resting on the outskirts of Langport, Somerset. (Ref. 1074556)
- Wi-fi
- Off-road parking
- Hot Tub
- Dishwasher
- Washing machine
- Baby-friendly
- Sky TV
3 nights from Sun 31st May £902
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- Sleeps7
- Bedrooms3
- PetsNo
This all-ground-floor cottage rests in the charming seaside resort of Swanage on the Jurassic Coast of Dorset. (Ref. 1012027)
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
3 nights from Fri 29th May
was £751£739Book nowLast booked yesterday
Make the most of the May half term with a relaxing and memorable stay in a holiday cottage.
As the spring season transitions into summer, it's the perfect time to head away and explore picturesque destinations and soak up the beauty of the countryside or coastline.
From cosy rural retreats to luxury seaside escapes, find your perfect getaway this May half term.
Why stay in a Holiday Cottages for May Half Term?
Staying in a holiday cottage in Dorset during May half term is the perfect way to embrace the beauty of late spring.
Dorset’s mild climate comes alive in May, with blooming flowers and picturesque coastal towns and villages which offer an idyllic backdrop for your getaway.
May half term is also the perfect time to visit Dorset, with some of the county’s iconic attractions less crowded than in the peak summer months.
So, whether you’re planning a family adventure or a group holiday, a stay in a Dorset holiday cottage during May half term allows you to tailor your trip to your pace.
Places to visit from Holiday Cottages in in May Half Term
May half term is a wonderful time to explore Dorset, with its vibrant landscapes and family-friendly attractions offering something for everyone.
If you are into history, then make sure you head to Corfe Castle, this spectacular ruin allows you to take in the stunning views of the region whilst also showcasing the rich history of the area, transporting you back in time.
Next on your adventures should be the stunning Jurassic Coast, a UNESCO World Heritage Site, take a walk along some of the dramatic cliffs, thanks to the fantastic coastal footpaths and head to the iconic landmarks of this coastline, from Durdle Door to Lulworth Cove.
For great family days out, don’t miss the chance to head to attractions such as the Monkey World Ape Rescue Centre or the Tank Museum, both offering educational experiences for all ages.
With so much to see and do, Dorset is the ideal destination for a memorable May half-term holiday.
Types of Dorset Holiday Cottages
Secure your next half term break with a holiday cottage over May half-term today!
Looking at other options, then check out cottages with a thatched roof or cosy roaring fire. Or why not take a look at some luxury holiday cottages that boast a hot tub or swimming pool.
Looking for the perfect romantic getaway, a family get together then these should guide you in the right direction. For more half term breaks, browse February half term breaks and October half term breaks. If you are wanting a break over the festive season, then view Christmas breaks in Dorset, for those seeking a magical holiday this year.
Explore the full collection of Dorset holiday cottages today!