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May Half-Term Breaks

441 properties found

A living room with a sofa, chair, coffee table and television at 123 On The Sea – Victoria’s Place in Weymouth

123 On The Sea - Victoria’s Place

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

Fri 30th Apr for 3 nights

£385

A window with champagne and glasses overlooking the sea at 123 On The Sea – The Eaves in Weymouth
New

123 On The Sea - The Eaves

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

Fri 30th Apr for 3 nights

£390

A living room with furniture including a sofa and a dresser at 4 The Beaches in Weymouth
New

4 The Beaches

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

Tue 4th May for 3 nights

£580

An exterior view of a rustic building with tiled roof and multiple glass doors opening onto a cobblestone courtyard with potted plants and a garden area at The Shippon in Honiton

The Shippon

Honiton, Devon

2 Guests
1 Beds
No pets
Wifi

Mon 3rd May for 3 nights

£642

An entrance with double doors and window at Frome Gazey in Frampton
New

Frome Gazey Barn

Frampton, Dorset

2 Guests
1 Beds
No pets
Wifi

Fri 30th Apr for 3 nights

£532

A hallway with door opening to the sea at 123 On The Sea - The Cubby in Weymouth
New

123 On The Sea - The Cubby

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

Fri 30th Apr for 3 nights

£374

An outdoor patio area with tables, chairs, and flower beds outside cream walls with blue doors and windows at The Compass in Swanage

The Compass

Swanage, Dorset

2 Guests
1 Beds
No pets
Wifi

Sun 2nd May for 3 nights

£372

A stone cottage with a white door and windows a wooden gate and gravel driveway at Little Brook in Nottington near Weymouth

Little Brook

Nottington near Weymouth, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

Fri 30th Apr for 3 nights

£556

A white house with a glass porch and wooden railings on a paved patio at Village View in Burton Bradstock

Village View

Burton Bradstock, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

Sun 2nd May for 3 nights

£504

A living room with a sofa and coffee table at 6 Bedford Place in Bridport

No. 6

Bridport, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

Fri 30th Apr for 3 nights

£472

A small stone patio with a round table and chairs next to a wooden bench outside a stone house at Tiddlers Cottage in Uploders near Bridport

Tiddlers Cottage

Uploders near Bridport, Dorset

2 Guests
1 Beds
No pets
Wifi

Tue 4th May for 3 nights

£407

An outdoor patio with furniture and plants at Flat 1, 2 Wooperton Street Weymouth
New

The Secret Courtyard

Weymouth, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

Fri 30th Apr for 3 nights

£569

A garden with a table and chairs at Tipsy Turtle in Weymouth

Tipsy Turtle

Portland, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

Fri 7th May for 3 nights

£442

A house with a garage and garden at Farthing Cottage in Corfe Castle
New

Farthing Cottage

Corfe Castle, Dorset

4 Guests
2 Beds
Pet Friendly
Wifi

Sun 2nd May for 3 nights

£448

A small brick and stone building with a slate roof surrounded by trees and bushes in a garden at The Folly at Castlebridge in Mere

The Folly at Castlebridge

Mere, Wiltshire

2 Guests
1 Beds
Pet Friendly
Wifi

Fri 30th Apr for 3 nights

£564

A small dining area with a round table set for four near a window with a view of the beach and ocean at 5 The Beaches Weymouth

5 The Beaches

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

Fri 7th May for 3 nights

£527

An outside view of a small brick building with a red door and a window with plants and a green utility box at Fountain Cottage in Weymouth

Fountain Cottage

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

Fri 30th Apr for 3 nights

£495

An outdoor view of a building with a driveway at Frome View in Wool

Frome View

Wool, Dorset

2 Guests
1 Beds
No pets
Wifi

Fri 30th Apr for 3 nights

£661

A thatched roof cottage next to a white building with parking spaces near trees at Thimble Cottage in Winterborne Stickland near Blandford Forum

Thimble Cottage

Winterborne Stickland near Blandford Forum, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

Fri 7th May for 3 nights

£606

A small white building with a shingled roof and two small trees in pots on either side of the door at Roundham Cottage in West Bay

Roundham Cottage

West Bay, Dorset

2 Guests
1 Beds
No pets
Wifi

Fri 30th Apr for 3 nights

£538

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!  

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