May Half-Term Breaks
440 properties found
440 properties found

123 On The Sea - The Eaves
Weymouth, Dorset
123 On The Sea – The Eaves is a delightful apartment resting in Weymouth, Dorset, featuring beach views, off-road parking, and nearby attractions.
- Wifi
- Baby Friendly
- Dishwasher
- Off Road Parking
Fri 30th Apr for 3 nights
£390

123 On The Sea - Victoria’s Place
Weymouth, Dorset
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.
- Wifi
- Baby Friendly
- Dishwasher
- Off Road Parking
Fri 30th Apr for 3 nights
£385

The Shippon
Honiton, Devon
The Shippon is a spacious and inviting home, with characterful yet chic features, perfect for a romantic getaway at Lower Lye, in the Blackdown Hills AONB.
- Wifi
- Baby Friendly
- Dishwasher
- EV Charging
- Ground Floor Bedroom
- Hot Tub
- Washing Machine
Mon 3rd May for 3 nights
£642

123 On The Sea - The Cubby
Weymouth, Dorset
The Cubby is a delightful first-floor apartment in Weymouth, Dorset, boasting a central location close to shops, pubs, beaches and coastal attractions.
- Wifi
- Dishwasher
Fri 30th Apr for 3 nights
£374

4 The Beaches
Weymouth, Dorset
4 The Beaches is a delightful beach view apartment in Weymouth, Dorset, featuring sea views, a furnished balcony, parking permit, and beachside appeal throughout.
- Wifi
- Dishwasher
- Washing Machine
Tue 4th May for 3 nights
£580

Frome Gazey Barn
Frampton, Dorset
Frome Gazey Barn is an inviting house in Frampton, Dorset, boasting a mezzanine double bedroom, woodburning stove, and furnished courtyard patio for two.
- Wifi
- Dishwasher
- EV Charging
- Washing Machine
Fri 30th Apr for 3 nights
£532

The Compass
Swanage, Dorset
This first floor flat is located in the lively town of Swanage in Dorset and can sleep two people in one bedroom.
- Wifi
- Dishwasher
- Off Road Parking
- Washing Machine
Sun 2nd May for 3 nights
£372

Little Brook
Nottington near Weymouth, Dorset
A charming, stone-built property resting within the village of Nottington, Dorset.
- Wifi
- EV Charging
- Ground Floor Bedroom
- Off Road Parking
- Washing Machine
Fri 30th Apr for 3 nights
£556

Village View
Burton Bradstock, Dorset
A romantic retreat resting within the village of Burton Bradstock.
- Wifi
- Baby Friendly
- Dishwasher
- Ground Floor Bedroom
- Off Road Parking
- Washing Machine
Sun 2nd May for 3 nights
£504

Tipsy Turtle
Portland, Dorset
Tipsy Turtle is an inviting, ground-floor apartment in Portland, Dorset, close to the beach, offering open-plan living and an enclosed courtyard.
- Wifi
- Ground Floor Bedroom
- Off Road Parking
Fri 7th May for 3 nights
£442

Tiddlers Cottage
Uploders near Bridport, Dorset
This attractive, one-bedroom cottage resides in Uploders near Bridport, Dorset.
- Wifi
- Off Road Parking
- Washing Machine
Tue 4th May for 3 nights
£407

The Folly at Castlebridge
Mere, Wiltshire
Set in wonderfully private surroundings within the grounds of the owners house, The Folly is a real gem if you're looking for peace and quiet in an exceptional location.
- Wifi
- Dishwasher
- Off Road Parking
- Washing Machine
Fri 30th Apr for 3 nights
£564

5 The Beaches
Weymouth, Dorset
A modern second-floor apartment in the popular Dorset resort of Weymouth.
- Wifi
- Dishwasher
Fri 7th May for 3 nights
£527

Fountain Cottage
Weymouth, Dorset
A delightful cottage with charm and character but a modern touch.
- Wifi
- Baby Friendly
- Dishwasher
- Ground Floor Bedroom
- Off Road Parking
- Washing Machine
Fri 30th Apr for 3 nights
£495

Thimble Cottage
Winterborne Stickland near Blandford Forum, Dorset
Thimble Cottage near Blandford Forum, Dorset, sleeps two guests in one bedroom.
- Wifi
- Dishwasher
- EV Charging
- Off Road Parking
- Washing Machine
Fri 7th May for 3 nights
£524

Roundham Cottage
West Bay, Dorset
A pretty converted property within the popular coastal town of West Bay, Dorset.
- Wifi
- Ground Floor Bedroom
- Off Road Parking
Fri 30th Apr for 3 nights
£538

The Secret Courtyard
Weymouth, Dorset
The Secret Courtyard is a welcoming ground-floor apartment in Weymouth, Dorset, featuring contemporary styling, a bright kitchen and enclosed courtyard.
- Wifi
- Ground Floor Bedroom
- Washing Machine
Fri 30th Apr for 3 nights
£569

Frome View
Wool, Dorset
Frome View is a one-bedroom property in Wool, Dorset, and a well-proportioned retreat for couples, perfectly positioned for coast and countryside views.
- Wifi
- EV Charging
- Off Road Parking
- Washing Machine
Fri 30th Apr for 3 nights
£661

The Sunday School Room
Glanvilles Wootton, Dorset
The Sunday School Room, a romantic 19th-century cottage in Glanvilles Wootton, Dorset, offers a Japanese bath, underfloor heating, and a woodburning stove.
- Wifi
- Dishwasher
- Off Road Parking
- Washing Machine
Fri 30th Apr for 3 nights
£350
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!

