Your search returned 459 cottages.
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- Sleeps2
- Bedrooms1
- Pet FriendlyNo
123 On The Sea – Victoria’s Place is a beautifully appointed seafront apartment in Weymouth, Dorset, featuring beach views, private parking, and a bright open-plan layout. (Ref. 1133962)
- Wi-fi
- Off-road parking
- Dishwasher
- Baby-friendly
3 nights from Sun 2nd May From £578
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- Sleeps10
- Bedrooms5
- Pet FriendlyYes
Harbins Farm is a farmhouse dating back 200 years, in Glanvilles Wootton Near Sherborne, Dorset, pet-friendly with woodburning stoves. (Ref. 1200098)
- Pets go free
- Wi-fi
- Off-road parking
- Ground floor bedroom
- Dishwasher
- Washing machine
3 nights from Sun 2nd May From £1060
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- Sleeps8
- Bedrooms4
- Pet FriendlyYes
The Watch House is a simply beautiful terraced townhouse nestled into the bustling seaside town of Weymouth, Dorset, close to shops and beaches. (Ref. 1205646)
- Pets go free
- Wi-fi
- Dishwasher
- Washing machine
3 nights from Fri 30th Apr From £896
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- Sleeps4
- Bedrooms2
- Pet FriendlyNo
Beck House, a welcoming mews house within a secure gated development in the heart of Weymouth, just a short walk from the harbour, beach and amenities. (Ref. 1201741)
- Wi-fi
- Dishwasher
- Washing machine
3 nights from Sun 2nd May From £498
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- Sleeps6
- Bedrooms3
- Pet FriendlyYes
Woodbine Cottage is a welcoming holiday home in Weymouth, Dorset, boasting a woodburning stove, enclosed rear patio and easy access to local amenities. (Ref. 1203009)
- Pets go free
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
- Baby-friendly
3 nights from Fri 7th May From £685
Book nowLast booked 2 days ago -
- Sleeps4
- Bedrooms2
- Pet FriendlyNo
Swanny View is a welcoming caravan featuring open‑plan living, enclosed decking with furniture, EV charging on‑site and easy access to local amenities. (Ref. 1201196)
- Wi-fi
- Off-road parking
- Ground floor bedroom
3 nights from Sun 2nd May From £412
Book nowLast booked yesterday -
- Sleeps6
- Bedrooms3
- Pet FriendlyNo
Rose Cottage, a charming thatched cottage nestled in Osmington, within Dorset National Landscape, boasts a large garden and proximity to local amenities. (Ref. 1200211)
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
3 nights from Fri 30th Apr From £727
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- Sleeps2
- Bedrooms1
- Pet FriendlyNo
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 3rd May From £623
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- Sleeps6
- Bedrooms3
- Pet FriendlyYes
Fairways House is a welcoming, semi-detached home resting in the riverside town of Weymouth, Dorset, with close by shops, pubs, a garden, and parking. (Ref. 1177908)
- Pets go free
- Wi-fi
- Off-road parking
- Dishwasher
- Washing machine
3 nights from Fri 30th Apr From £717
Book nowLast booked yesterday -
- Sleeps5
- Bedrooms3
- Pet FriendlyNo
Cove Cottage is a well-located cottage in Weymouth, Dorset, boasting close proximity to the beach and easy access to local shops and nearby amenities. (Ref. 1094256)
- Wi-fi
- Off-road parking
- Washing machine
3 nights from Fri 30th Apr From £683
Book 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!