May Half Term Holiday Cottages

May Half Term Holiday Cottages

With a cool breeze and warm sunshine, May marks the start of summer and many happy times to come. Kick start your summer properly and hop in the car; a holiday in a luxury self-catering cottage awaits. Browse through our list of 805 available cottages and find your favourite. All of our cottages are handpicked; personally inspected and fully equipped so your holiday is the best it can be.Read more

Spend your days exploring deep, green countryside and skim stones across lazy streams. Follow the scent of salty air and head to the coast, spending long days on the beach flitting between soft sands and cool sea. Perch on a bench and watch as life goes by, before heading to a local restaurant to dine on fresh, local produce lovingly crafted and prepared by skilled hands. Then, when you've had your fill of exploring, turn your attention to relaxing. Throw yourself into the holiday spirit and land in your own private self-catering cottage, primed and ready for you. An early summer break in your own slice of paradise can give you the chance to unwind, catch up and settle into a slower, more considered rhythm.  

Spend your May-Half Term in a Luxury Retreat

Whether you are looking for a solo retreat or want to bring the whole family away for a much-needed break, May half term provides ample opportunity to escape to greener grass for a while. However you'd like to spend your time, our cottages offer wide variety and consistent quality. Many of our cottages are dog-friendly too, meaning everyone can join in this May half term. 

Our exclusive ferry discounts will make your island trip with Classic plain sailing.

We have 805 cottages available for May half term

Seymour Barn is a 2 bedroom, dog friendly barn conversion in Bridport, Dorset.
  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1020

Seymour Barn

5314

2 bedroom, dog friendly barn conversion in Bridport, Dorset.


With the bustling market town of Bridport within striking distance, this beautiful barn conversion is the perfect home-away-from-home. A delightful spot to explore all the beauty a...

  • Sleeps 4 + cot
  • Dogs welcome
  • Changeover Fri

7 nights from £1020

Pheasant Cottage is a 1 bedroom self catering cottage in Tealby.
  • Sleeps 2
  • No pets
  • Changeover Sat

From £101 per night

Pheasant Cottage

5326

1 bedroom self catering cottage in Tealby.


Pheasant Cottage is a charming and cosy retreat nestled in the beautiful rear garden of the owners' property and located in Tealby, the most beautiful village in the Lincolnshire W...

  • Sleeps 2
  • No pets
  • Changeover Sat

From £101 per night

The Swallows is a 3 bedroom, dog friendly holiday cottage near Chagford, Dartmoor.
  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1153

The Swallows

5294

3 bedroom, dog friendly holiday cottage near Chagford, Dartmoor.


The Swallows, a fabulous rural retreat awaits. Nestled in the most picturesque countryside, surrounded by the most special sights and sounds mother nature can offer, along with bei...

  • Sleeps 6 + 2 cots
  • Dogs welcome
  • Changeover Sat

7 nights from £1153

Rose Cottage is a 3 bedroom self catering cottage near the beach in Hythe.
  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £925

Rose Cottage

5304

3 bedroom self catering cottage near the beach in Hythe.


Rose Cottage is an enchanting Grade II Listed period property situated in the heart of Hythe within walking distance of the Royal Military Canal, the seafront, and local amenities....

  • Sleeps 6 + cot
  • No pets
  • Changeover Fri

7 nights from £925

Each and every one of our cottages is fully equipped with everything you’ll need on holiday.

Shar Mar is a 2 bedroom self catering cottage near Falmouth, West Cornwall.
  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £730

Shar Mar

5351

2 bedroom self catering cottage near Falmouth, West Cornwall.


A lovely dormer bungalow set within large, mature garden found in the heart of the charming village of Constantine. This property offers a home-from-home experience for families or...

  • Sleeps 4 + 2 cots
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £730

The Dovecote is a 1 bedroom self catering cottage near Chippenham.
  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £744

The Dovecote

5361

1 bedroom self catering cottage near Chippenham.


Peaceful, tranquil and surrounded by gorgeous greenery, welcome to The Dovecote. The clue is in the name, this pretty little hideaway is perfect for a romantic getaway and has been...

  • Sleeps 2 + cot
  • No pets
  • Changeover Fri

7 nights from £744

September Cottage is a 2 bedroom, dog friendly cottage near the beach near St. Mawes
  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £837

September Cottage

5329

2 bedroom, dog friendly cottage near the beach near St. Mawes


Nestled in the heart of the charming Roseland village of St Mawes, September Cottage is a delightful holiday abode, perfectly placed just moments away from the gorgeous beaches and...

  • Sleeps 4 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £837

Lofty Heights is a 1 bedroom holiday apartment with sea views in Shaldon, South Devon.
  • Sleeps 2 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £923

Lofty Heights

5337

1 bedroom holiday apartment with sea views in Shaldon, South Devon.


Looking for that special retreat for two, if so, welcome to Lofty Heights which is nestled in the very sought-after village of Shaldon, just moments from a fabulous sandy beach and...

  • Sleeps 2 + 2 cots
  • No pets
  • Changeover Sat

7 nights from £923

The Retreat is a 3 bedroom holiday apartment with sea views in Shaldon, South Devon.
  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £1408

The Retreat

5338

3 bedroom holiday apartment with sea views in Shaldon, South Devon.


Welcome to The Retreat, a gorgeous family holiday home, nestled in the beautiful village of Shaldon. Shaldon and The Retreat offer something special for all ages, from the sandy be...

  • Sleeps 6 + cot
  • No pets
  • Changeover Sat

7 nights from £1408

Green Place is a 1 bedroom, dog friendly cottage within walking distance of the cathedral in Wells, Somerset.
  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £473

Green Place

5313

1 bedroom, dog friendly cottage within walking distance of the cathedral in Wells, Somerset.


Wind your way through the historic streets of Wells to find Green Place nestling in a quiet mews offering a romantic getaway. With a vibrant and bustling high street, the city of W...

  • Sleeps 2 + cot
  • Dogs welcome (1 only)
  • Changeover Fri

7 nights from £473

Readymade beds and fluffy towels; this simple but appreciated welcome is standard with us.

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